Enantioseparation Using Cellulose Tris(3,5-dimethylphenylcarbamate) as Chiral Stationary Phase for HPLC: Influence of Molecular Weight of Cellulose †
Identifieur interne : 001839 ( Ncbi/Merge ); précédent : 001838; suivant : 001840Enantioseparation Using Cellulose Tris(3,5-dimethylphenylcarbamate) as Chiral Stationary Phase for HPLC: Influence of Molecular Weight of Cellulose †
Auteurs : Yuji Okada ; Chiyo Yamamoto ; Masami Kamigaito ; Yuan Gao ; Jun Shen ; Yoshio OkamotoSource :
- Molecules [ 1420-3049 ] ; 2016.
Descripteurs français
- KwdFr :
- MESH :
- analogues et dérivés : Cellulose.
- synthèse chimique : Cellulose, Phényl-carbamates.
- Acides phosphoriques, Cellulose, Chromatographie en phase liquide à haute performance, Hydrolyse, Masse moléculaire, Phényl-carbamates, Structure moléculaire, Stéréoisomérie.
English descriptors
- KwdEn :
- Cellulose (analogs & derivatives), Cellulose (chemical synthesis), Cellulose (chemistry), Chromatography, High Pressure Liquid (methods), Hydrolysis, Molecular Structure, Molecular Weight, Phenylcarbamates (chemical synthesis), Phenylcarbamates (chemistry), Phosphoric Acids (chemistry), Stereoisomerism.
- MESH :
- chemical , analogs & derivatives : Cellulose.
- chemical , chemical synthesis : Cellulose, Phenylcarbamates.
- chemical , chemistry : Cellulose, Phenylcarbamates, Phosphoric Acids.
- methods : Chromatography, High Pressure Liquid.
- Hydrolysis, Molecular Structure, Molecular Weight, Stereoisomerism.
Abstract
The cellulose oligomers with different degrees of polymerization (DP), 7, 11, 18, 24, 26, 40 and 52, were prepared by hydrolysis of microcrystalline cellulose with phosphoric acid. These oligomers including the starting microcrystalline cellulose (DP 124) were converted to tris(3,5-dimethylphenylcarbamate) (CDMPC) derivatives by the reaction with an excess of 3,5-dimethylphenyl isocyanate to be used as the chiral stationary phase (CSP) in high-performance liquid chromatography (HPLC). The structures of the CDMPC derivatives were investigated by infrared spectroscopy (IR), 1H-NMR, circular dichroism (CD) and size exclusion chromatography (SEC), and the DPs of the derivatives estimated by SEC agreed with those estimated by 1H-NMR. After coating the derivatives on silica gel, their chiral recognition abilities were evaluated using eight racemates under a normal phase condition with a hexane-2-propanol (99/1) mixture as an eluent. The chiral recognition abilities of 7- and 11-mers, particularly the former, were lower than those of the higher oligomers from DP 18 to 52, which had rather similar abilities to that of 124-mer, although the abilities depended on the racemates. DP 18 seems to be sufficient for CDMPC to exhibit chiral recognition similar to that of the CDMPC with larger DPs.
Url:
DOI: 10.3390/molecules21111484
PubMed: 27834832
PubMed Central: 6273561
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464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation></author><author><name sortKey="Kamigaito, Masami" sort="Kamigaito, Masami" uniqKey="Kamigaito M" first="Masami" last="Kamigaito">Masami Kamigaito</name><affiliation><nlm:aff id="af1-molecules-21-01484">Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation></author><author><name sortKey="Gao, Yuan" sort="Gao, Yuan" uniqKey="Gao Y" first="Yuan" last="Gao">Yuan Gao</name><affiliation><nlm:aff id="af2-molecules-21-01484">Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, 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rid="fn1-molecules-21-01484">†</xref></title><author><name sortKey="Okada, Yuji" sort="Okada, Yuji" uniqKey="Okada Y" first="Yuji" last="Okada">Yuji Okada</name><affiliation><nlm:aff id="af1-molecules-21-01484">Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation></author><author><name sortKey="Yamamoto, Chiyo" sort="Yamamoto, Chiyo" uniqKey="Yamamoto C" first="Chiyo" last="Yamamoto">Chiyo Yamamoto</name><affiliation><nlm:aff id="af1-molecules-21-01484">Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation></author><author><name sortKey="Kamigaito, Masami" sort="Kamigaito, Masami" uniqKey="Kamigaito M" first="Masami" last="Kamigaito">Masami Kamigaito</name><affiliation><nlm:aff id="af1-molecules-21-01484">Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation></author><author><name sortKey="Gao, Yuan" sort="Gao, Yuan" uniqKey="Gao Y" first="Yuan" last="Gao">Yuan Gao</name><affiliation><nlm:aff id="af2-molecules-21-01484">Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China;<email>gaoyuan1@hrbeu.edu.cn</email></nlm:aff></affiliation></author><author><name sortKey="Shen, Jun" sort="Shen, Jun" uniqKey="Shen J" first="Jun" last="Shen">Jun Shen</name><affiliation><nlm:aff id="af2-molecules-21-01484">Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China;<email>gaoyuan1@hrbeu.edu.cn</email></nlm:aff></affiliation></author><author><name sortKey="Okamoto, Yoshio" sort="Okamoto, Yoshio" uniqKey="Okamoto Y" first="Yoshio" last="Okamoto">Yoshio Okamoto</name><affiliation><nlm:aff id="af1-molecules-21-01484">Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation><affiliation><nlm:aff id="af2-molecules-21-01484">Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China;<email>gaoyuan1@hrbeu.edu.cn</email></nlm:aff></affiliation></author></analytic><series><title level="j">Molecules</title><idno type="eISSN">1420-3049</idno><imprint><date when="2016">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Cellulose (analogs & derivatives)</term><term>Cellulose (chemical synthesis)</term><term>Cellulose (chemistry)</term><term>Chromatography, High Pressure Liquid (methods)</term><term>Hydrolysis</term><term>Molecular Structure</term><term>Molecular Weight</term><term>Phenylcarbamates (chemical synthesis)</term><term>Phenylcarbamates (chemistry)</term><term>Phosphoric Acids (chemistry)</term><term>Stereoisomerism</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acides phosphoriques ()</term><term>Cellulose ()</term><term>Cellulose (analogues et dérivés)</term><term>Cellulose (synthèse chimique)</term><term>Chromatographie en phase liquide à haute performance ()</term><term>Hydrolyse</term><term>Masse moléculaire</term><term>Phényl-carbamates ()</term><term>Phényl-carbamates (synthèse chimique)</term><term>Structure moléculaire</term><term>Stéréoisomérie</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Cellulose</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Cellulose</term><term>Phenylcarbamates</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Cellulose</term><term>Phenylcarbamates</term><term>Phosphoric Acids</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Cellulose</term></keywords><keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Chromatography, High Pressure Liquid</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Cellulose</term><term>Phényl-carbamates</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Hydrolysis</term><term>Molecular Structure</term><term>Molecular Weight</term><term>Stereoisomerism</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Acides phosphoriques</term><term>Cellulose</term><term>Chromatographie en phase liquide à haute performance</term><term>Hydrolyse</term><term>Masse moléculaire</term><term>Phényl-carbamates</term><term>Structure moléculaire</term><term>Stéréoisomérie</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The cellulose oligomers with different degrees of polymerization (DP), 7, 11, 18, 24, 26, 40 and 52, were prepared by hydrolysis of microcrystalline cellulose with phosphoric acid. These oligomers including the starting microcrystalline cellulose (DP 124) were converted to tris(3,5-dimethylphenylcarbamate) (CDMPC) derivatives by the reaction with an excess of 3,5-dimethylphenyl isocyanate to be used as the chiral stationary phase (CSP) in high-performance liquid chromatography (HPLC). The structures of the CDMPC derivatives were investigated by infrared spectroscopy (IR), <sup>1</sup>H-NMR, circular dichroism (CD) and size exclusion chromatography (SEC), and the DPs of the derivatives estimated by SEC agreed with those estimated by <sup>1</sup>H-NMR. After coating the derivatives on silica gel, their chiral recognition abilities were evaluated using eight racemates under a normal phase condition with a hexane-2-propanol (99/1) mixture as an eluent. The chiral recognition abilities of 7- and 11-mers, particularly the former, were lower than those of the higher oligomers from DP 18 to 52, which had rather similar abilities to that of 124-mer, although the abilities depended on the racemates. DP 18 seems to be sufficient for CDMPC to exhibit chiral recognition similar to that of the CDMPC with larger DPs.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Allenmark, S G" uniqKey="Allenmark S">S.G. Allenmark</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Carreira, E M" uniqKey="Carreira E">E.M. Carreira</name></author><author><name sortKey="Yamamoto, H" uniqKey="Yamamoto H">H. Yamamoto</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kuang, X" uniqKey="Kuang X">X. Kuang</name></author><author><name sortKey="Ma, Y" uniqKey="Ma Y">Y. Ma</name></author><author><name sortKey="Su, H" uniqKey="Su H">H. Su</name></author><author><name sortKey="Zhang, J" uniqKey="Zhang J">J. Zhang</name></author><author><name sortKey="Dong, Y B" uniqKey="Dong Y">Y.-B. Dong</name></author><author><name sortKey="Tang, B" uniqKey="Tang B">B. Tang</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Shimomura, K" uniqKey="Shimomura K">K. Shimomura</name></author><author><name sortKey="Ikai, T" uniqKey="Ikai T">T. Ikai</name></author><author><name sortKey="Kanoh, S" uniqKey="Kanoh S">S. Kanoh</name></author><author><name sortKey="Yashima, E" uniqKey="Yashima E">E. Yashima</name></author><author><name sortKey="Maeda, K" uniqKey="Maeda K">K. Maeda</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kupai, J" uniqKey="Kupai J">J. Kupai</name></author><author><name sortKey="Rojik, E" uniqKey="Rojik E">E. Rojik</name></author><author><name sortKey="Huszthy, P" uniqKey="Huszthy P">P. Huszthy</name></author><author><name sortKey="Szekely, G" uniqKey="Szekely G">G. Szekely</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Chankvetadze, B" uniqKey="Chankvetadze B">B. Chankvetadze</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Shen, J" uniqKey="Shen J">J. Shen</name></author><author><name sortKey="Ikai, T" uniqKey="Ikai T">T. Ikai</name></author><author><name sortKey="Okamoto, Y" uniqKey="Okamoto Y">Y. Okamoto</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Shen, J" uniqKey="Shen J">J. Shen</name></author><author><name sortKey="Okamoto, Y" uniqKey="Okamoto Y">Y. Okamoto</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Aburatani, R" uniqKey="Aburatani R">R. Aburatani</name></author><author><name sortKey="Okamoto, Y" uniqKey="Okamoto Y">Y. Okamoto</name></author><author><name sortKey="Hatada, K" uniqKey="Hatada K">K. Hatada</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kasuya, N" uniqKey="Kasuya N">N. Kasuya</name></author><author><name sortKey="Kusaka, Y" uniqKey="Kusaka Y">Y. Kusaka</name></author><author><name sortKey="Habu, N" uniqKey="Habu N">N. Habu</name></author><author><name sortKey="Ohnishi, A" uniqKey="Ohnishi A">A. Ohnishi</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Isogai, A" uniqKey="Isogai A">A. Isogai</name></author><author><name sortKey="Usuda, M" uniqKey="Usuda M">M. Usuda</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kaida, Y" uniqKey="Kaida Y">Y. Kaida</name></author><author><name sortKey="Okamoto, Y" uniqKey="Okamoto Y">Y. Okamoto</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Yamamoto, C" uniqKey="Yamamoto C">C. Yamamoto</name></author><author><name sortKey="Yashima, E" uniqKey="Yashima E">E. Yashima</name></author><author><name sortKey="Okamoto, Y" uniqKey="Okamoto Y">Y. Okamoto</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Okamoto, Y" uniqKey="Okamoto Y">Y. Okamoto</name></author><author><name sortKey="Kawashima, M" uniqKey="Kawashima M">M. Kawashima</name></author><author><name sortKey="Hatada, K" uniqKey="Hatada K">K. Hatada</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Koller, M" uniqKey="Koller M">M. Koller</name></author><author><name sortKey="Rimbock, K H" uniqKey="Rimbock K">K.-H. Rimböck</name></author><author><name sortKey="Mannschrek, A" uniqKey="Mannschrek A">A. Mannschrek</name></author></analytic></biblStruct></listBibl></div1></back></TEI><double pmid="27834832"><pmc><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Enantioseparation Using Cellulose Tris(3,5-dimethylphenylcarbamate) as Chiral Stationary Phase for HPLC: Influence of Molecular Weight of Cellulose <xref ref-type="author-notes" rid="fn1-molecules-21-01484">†</xref></title><author><name sortKey="Okada, Yuji" sort="Okada, Yuji" uniqKey="Okada Y" first="Yuji" last="Okada">Yuji Okada</name><affiliation><nlm:aff id="af1-molecules-21-01484">Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation></author><author><name sortKey="Yamamoto, Chiyo" sort="Yamamoto, Chiyo" uniqKey="Yamamoto C" first="Chiyo" last="Yamamoto">Chiyo Yamamoto</name><affiliation><nlm:aff id="af1-molecules-21-01484">Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation></author><author><name sortKey="Kamigaito, Masami" sort="Kamigaito, Masami" uniqKey="Kamigaito M" first="Masami" last="Kamigaito">Masami Kamigaito</name><affiliation><nlm:aff id="af1-molecules-21-01484">Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation></author><author><name sortKey="Gao, Yuan" sort="Gao, Yuan" uniqKey="Gao Y" first="Yuan" last="Gao">Yuan Gao</name><affiliation><nlm:aff id="af2-molecules-21-01484">Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China;<email>gaoyuan1@hrbeu.edu.cn</email></nlm:aff></affiliation></author><author><name sortKey="Shen, Jun" sort="Shen, Jun" uniqKey="Shen J" first="Jun" last="Shen">Jun Shen</name><affiliation><nlm:aff id="af2-molecules-21-01484">Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China;<email>gaoyuan1@hrbeu.edu.cn</email></nlm:aff></affiliation></author><author><name sortKey="Okamoto, Yoshio" sort="Okamoto, Yoshio" uniqKey="Okamoto Y" first="Yoshio" last="Okamoto">Yoshio Okamoto</name><affiliation><nlm:aff id="af1-molecules-21-01484">Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation><affiliation><nlm:aff id="af2-molecules-21-01484">Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China;<email>gaoyuan1@hrbeu.edu.cn</email></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">27834832</idno><idno type="pmc">6273561</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273561</idno><idno type="RBID">PMC:6273561</idno><idno type="doi">10.3390/molecules21111484</idno><date when="2016">2016</date><idno type="wicri:Area/Pmc/Corpus">000F28</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000F28</idno><idno type="wicri:Area/Pmc/Curation">000F28</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000F28</idno><idno type="wicri:Area/Pmc/Checkpoint">000B82</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000B82</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Enantioseparation Using Cellulose Tris(3,5-dimethylphenylcarbamate) as Chiral Stationary Phase for HPLC: Influence of Molecular Weight of Cellulose <xref ref-type="author-notes" rid="fn1-molecules-21-01484">†</xref></title><author><name sortKey="Okada, Yuji" sort="Okada, Yuji" uniqKey="Okada Y" first="Yuji" last="Okada">Yuji Okada</name><affiliation><nlm:aff id="af1-molecules-21-01484">Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation></author><author><name sortKey="Yamamoto, Chiyo" sort="Yamamoto, Chiyo" uniqKey="Yamamoto C" first="Chiyo" last="Yamamoto">Chiyo Yamamoto</name><affiliation><nlm:aff id="af1-molecules-21-01484">Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation></author><author><name sortKey="Kamigaito, Masami" sort="Kamigaito, Masami" uniqKey="Kamigaito M" first="Masami" last="Kamigaito">Masami Kamigaito</name><affiliation><nlm:aff id="af1-molecules-21-01484">Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation></author><author><name sortKey="Gao, Yuan" sort="Gao, Yuan" uniqKey="Gao Y" first="Yuan" last="Gao">Yuan Gao</name><affiliation><nlm:aff id="af2-molecules-21-01484">Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China;<email>gaoyuan1@hrbeu.edu.cn</email></nlm:aff></affiliation></author><author><name sortKey="Shen, Jun" sort="Shen, Jun" uniqKey="Shen J" first="Jun" last="Shen">Jun Shen</name><affiliation><nlm:aff id="af2-molecules-21-01484">Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China;<email>gaoyuan1@hrbeu.edu.cn</email></nlm:aff></affiliation></author><author><name sortKey="Okamoto, Yoshio" sort="Okamoto, Yoshio" uniqKey="Okamoto Y" first="Yoshio" last="Okamoto">Yoshio Okamoto</name><affiliation><nlm:aff id="af1-molecules-21-01484">Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan;<email>column_okd@yahoo.co.jp</email> (Y.O.);<email>chiyo@chem.suzuka-ct.ac.jp</email> (C.Y.);<email>kamigait@apchem.nagoya-u.ac.jp</email> (M.K.)</nlm:aff></affiliation><affiliation><nlm:aff id="af2-molecules-21-01484">Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China;<email>gaoyuan1@hrbeu.edu.cn</email></nlm:aff></affiliation></author></analytic><series><title level="j">Molecules</title><idno type="eISSN">1420-3049</idno><imprint><date when="2016">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The cellulose oligomers with different degrees of polymerization (DP), 7, 11, 18, 24, 26, 40 and 52, were prepared by hydrolysis of microcrystalline cellulose with phosphoric acid. These oligomers including the starting microcrystalline cellulose (DP 124) were converted to tris(3,5-dimethylphenylcarbamate) (CDMPC) derivatives by the reaction with an excess of 3,5-dimethylphenyl isocyanate to be used as the chiral stationary phase (CSP) in high-performance liquid chromatography (HPLC). The structures of the CDMPC derivatives were investigated by infrared spectroscopy (IR), <sup>1</sup>H-NMR, circular dichroism (CD) and size exclusion chromatography (SEC), and the DPs of the derivatives estimated by SEC agreed with those estimated by <sup>1</sup>H-NMR. After coating the derivatives on silica gel, their chiral recognition abilities were evaluated using eight racemates under a normal phase condition with a hexane-2-propanol (99/1) mixture as an eluent. The chiral recognition abilities of 7- and 11-mers, particularly the former, were lower than those of the higher oligomers from DP 18 to 52, which had rather similar abilities to that of 124-mer, although the abilities depended on the racemates. DP 18 seems to be sufficient for CDMPC to exhibit chiral recognition similar to that of the CDMPC with larger DPs.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Allenmark, S G" uniqKey="Allenmark S">S.G. Allenmark</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Carreira, E M" uniqKey="Carreira E">E.M. Carreira</name></author><author><name sortKey="Yamamoto, H" uniqKey="Yamamoto H">H. Yamamoto</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kuang, X" uniqKey="Kuang X">X. Kuang</name></author><author><name sortKey="Ma, Y" uniqKey="Ma Y">Y. Ma</name></author><author><name sortKey="Su, H" uniqKey="Su H">H. Su</name></author><author><name sortKey="Zhang, J" uniqKey="Zhang J">J. Zhang</name></author><author><name sortKey="Dong, Y B" uniqKey="Dong Y">Y.-B. Dong</name></author><author><name sortKey="Tang, B" uniqKey="Tang B">B. Tang</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Shimomura, K" uniqKey="Shimomura K">K. Shimomura</name></author><author><name sortKey="Ikai, T" uniqKey="Ikai T">T. Ikai</name></author><author><name sortKey="Kanoh, S" uniqKey="Kanoh S">S. Kanoh</name></author><author><name sortKey="Yashima, E" uniqKey="Yashima E">E. Yashima</name></author><author><name sortKey="Maeda, K" uniqKey="Maeda K">K. Maeda</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kupai, J" uniqKey="Kupai J">J. Kupai</name></author><author><name sortKey="Rojik, E" uniqKey="Rojik E">E. Rojik</name></author><author><name sortKey="Huszthy, P" uniqKey="Huszthy P">P. Huszthy</name></author><author><name sortKey="Szekely, G" uniqKey="Szekely G">G. Szekely</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Chankvetadze, B" uniqKey="Chankvetadze B">B. Chankvetadze</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Shen, J" uniqKey="Shen J">J. Shen</name></author><author><name sortKey="Ikai, T" uniqKey="Ikai T">T. Ikai</name></author><author><name sortKey="Okamoto, Y" uniqKey="Okamoto Y">Y. Okamoto</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Shen, J" uniqKey="Shen J">J. Shen</name></author><author><name sortKey="Okamoto, Y" uniqKey="Okamoto Y">Y. Okamoto</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Aburatani, R" uniqKey="Aburatani R">R. Aburatani</name></author><author><name sortKey="Okamoto, Y" uniqKey="Okamoto Y">Y. Okamoto</name></author><author><name sortKey="Hatada, K" uniqKey="Hatada K">K. Hatada</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kasuya, N" uniqKey="Kasuya N">N. Kasuya</name></author><author><name sortKey="Kusaka, Y" uniqKey="Kusaka Y">Y. Kusaka</name></author><author><name sortKey="Habu, N" uniqKey="Habu N">N. Habu</name></author><author><name sortKey="Ohnishi, A" uniqKey="Ohnishi A">A. Ohnishi</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Isogai, A" uniqKey="Isogai A">A. Isogai</name></author><author><name sortKey="Usuda, M" uniqKey="Usuda M">M. Usuda</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kaida, Y" uniqKey="Kaida Y">Y. Kaida</name></author><author><name sortKey="Okamoto, Y" uniqKey="Okamoto Y">Y. Okamoto</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Yamamoto, C" uniqKey="Yamamoto C">C. Yamamoto</name></author><author><name sortKey="Yashima, E" uniqKey="Yashima E">E. Yashima</name></author><author><name sortKey="Okamoto, Y" uniqKey="Okamoto Y">Y. Okamoto</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Okamoto, Y" uniqKey="Okamoto Y">Y. Okamoto</name></author><author><name sortKey="Kawashima, M" uniqKey="Kawashima M">M. Kawashima</name></author><author><name sortKey="Hatada, K" uniqKey="Hatada K">K. Hatada</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Koller, M" uniqKey="Koller M">M. Koller</name></author><author><name sortKey="Rimbock, K H" uniqKey="Rimbock K">K.-H. Rimböck</name></author><author><name sortKey="Mannschrek, A" uniqKey="Mannschrek A">A. Mannschrek</name></author></analytic></biblStruct></listBibl></div1></back></TEI></pmc><pubmed><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Enantioseparation Using Cellulose Tris(3,5-dimethylphenylcarbamate) as Chiral Stationary Phase for HPLC: Influence of Molecular Weight of Cellulose.</title><author><name sortKey="Okada, Yuji" sort="Okada, Yuji" uniqKey="Okada Y" first="Yuji" last="Okada">Yuji Okada</name><affiliation wicri:level="1"><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. column_okd@yahoo.co.jp.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603</wicri:regionArea><wicri:noRegion>Nagoya 464-8603</wicri:noRegion></affiliation></author><author><name sortKey="Yamamoto, Chiyo" sort="Yamamoto, Chiyo" uniqKey="Yamamoto C" first="Chiyo" last="Yamamoto">Chiyo Yamamoto</name><affiliation wicri:level="1"><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. chiyo@chem.suzuka-ct.ac.jp.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603</wicri:regionArea><wicri:noRegion>Nagoya 464-8603</wicri:noRegion></affiliation></author><author><name sortKey="Kamigaito, Masami" sort="Kamigaito, Masami" uniqKey="Kamigaito M" first="Masami" last="Kamigaito">Masami Kamigaito</name><affiliation wicri:level="1"><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. kamigait@apchem.nagoya-u.ac.jp.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603</wicri:regionArea><wicri:noRegion>Nagoya 464-8603</wicri:noRegion></affiliation></author><author><name sortKey="Gao, Yuan" sort="Gao, Yuan" uniqKey="Gao Y" first="Yuan" last="Gao">Yuan Gao</name><affiliation wicri:level="1"><nlm:affiliation>Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China. gaoyuan1@hrbeu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001</wicri:regionArea><wicri:noRegion>Harbin 150001</wicri:noRegion></affiliation></author><author><name sortKey="Shen, Jun" sort="Shen, Jun" uniqKey="Shen J" first="Jun" last="Shen">Jun Shen</name><affiliation wicri:level="1"><nlm:affiliation>Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China. shenjun@hrbeu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001</wicri:regionArea><wicri:noRegion>Harbin 150001</wicri:noRegion></affiliation></author><author><name sortKey="Okamoto, Yoshio" sort="Okamoto, Yoshio" uniqKey="Okamoto Y" first="Yoshio" last="Okamoto">Yoshio Okamoto</name><affiliation wicri:level="1"><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. okamoto@apchem.nagoya-u.ac.jp.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603</wicri:regionArea><wicri:noRegion>Nagoya 464-8603</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2016">2016</date><idno type="RBID">pubmed:27834832</idno><idno type="pmid">27834832</idno><idno type="doi">10.3390/molecules21111484</idno><idno type="wicri:Area/PubMed/Corpus">000E97</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000E97</idno><idno type="wicri:Area/PubMed/Curation">000E97</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">000E97</idno><idno type="wicri:Area/PubMed/Checkpoint">001125</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">001125</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Enantioseparation Using Cellulose Tris(3,5-dimethylphenylcarbamate) as Chiral Stationary Phase for HPLC: Influence of Molecular Weight of Cellulose.</title><author><name sortKey="Okada, Yuji" sort="Okada, Yuji" uniqKey="Okada Y" first="Yuji" last="Okada">Yuji Okada</name><affiliation wicri:level="1"><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. column_okd@yahoo.co.jp.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603</wicri:regionArea><wicri:noRegion>Nagoya 464-8603</wicri:noRegion></affiliation></author><author><name sortKey="Yamamoto, Chiyo" sort="Yamamoto, Chiyo" uniqKey="Yamamoto C" first="Chiyo" last="Yamamoto">Chiyo Yamamoto</name><affiliation wicri:level="1"><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. chiyo@chem.suzuka-ct.ac.jp.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603</wicri:regionArea><wicri:noRegion>Nagoya 464-8603</wicri:noRegion></affiliation></author><author><name sortKey="Kamigaito, Masami" sort="Kamigaito, Masami" uniqKey="Kamigaito M" first="Masami" last="Kamigaito">Masami Kamigaito</name><affiliation wicri:level="1"><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. kamigait@apchem.nagoya-u.ac.jp.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603</wicri:regionArea><wicri:noRegion>Nagoya 464-8603</wicri:noRegion></affiliation></author><author><name sortKey="Gao, Yuan" sort="Gao, Yuan" uniqKey="Gao Y" first="Yuan" last="Gao">Yuan Gao</name><affiliation wicri:level="1"><nlm:affiliation>Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China. gaoyuan1@hrbeu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001</wicri:regionArea><wicri:noRegion>Harbin 150001</wicri:noRegion></affiliation></author><author><name sortKey="Shen, Jun" sort="Shen, Jun" uniqKey="Shen J" first="Jun" last="Shen">Jun Shen</name><affiliation wicri:level="1"><nlm:affiliation>Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China. shenjun@hrbeu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001</wicri:regionArea><wicri:noRegion>Harbin 150001</wicri:noRegion></affiliation></author><author><name sortKey="Okamoto, Yoshio" sort="Okamoto, Yoshio" uniqKey="Okamoto Y" first="Yoshio" last="Okamoto">Yoshio Okamoto</name><affiliation wicri:level="1"><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. okamoto@apchem.nagoya-u.ac.jp.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603</wicri:regionArea><wicri:noRegion>Nagoya 464-8603</wicri:noRegion></affiliation></author></analytic><series><title level="j">Molecules (Basel, Switzerland)</title><idno type="eISSN">1420-3049</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Cellulose (analogs & derivatives)</term><term>Cellulose (chemical synthesis)</term><term>Cellulose (chemistry)</term><term>Chromatography, High Pressure Liquid (methods)</term><term>Hydrolysis</term><term>Molecular Structure</term><term>Molecular Weight</term><term>Phenylcarbamates (chemical synthesis)</term><term>Phenylcarbamates (chemistry)</term><term>Phosphoric Acids (chemistry)</term><term>Stereoisomerism</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acides phosphoriques ()</term><term>Cellulose ()</term><term>Cellulose (analogues et dérivés)</term><term>Cellulose (synthèse chimique)</term><term>Chromatographie en phase liquide à haute performance ()</term><term>Hydrolyse</term><term>Masse moléculaire</term><term>Phényl-carbamates ()</term><term>Phényl-carbamates (synthèse chimique)</term><term>Structure moléculaire</term><term>Stéréoisomérie</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Cellulose</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Cellulose</term><term>Phenylcarbamates</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Cellulose</term><term>Phenylcarbamates</term><term>Phosphoric Acids</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Cellulose</term></keywords><keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Chromatography, High Pressure Liquid</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Cellulose</term><term>Phényl-carbamates</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Hydrolysis</term><term>Molecular Structure</term><term>Molecular Weight</term><term>Stereoisomerism</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Acides phosphoriques</term><term>Cellulose</term><term>Chromatographie en phase liquide à haute performance</term><term>Hydrolyse</term><term>Masse moléculaire</term><term>Phényl-carbamates</term><term>Structure moléculaire</term><term>Stéréoisomérie</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The cellulose oligomers with different degrees of polymerization (DP), 7, 11, 18, 24, 26, 40 and 52, were prepared by hydrolysis of microcrystalline cellulose with phosphoric acid. These oligomers including the starting microcrystalline cellulose (DP 124) were converted to tris(3,5-dimethylphenylcarbamate) (CDMPC) derivatives by the reaction with an excess of 3,5-dimethylphenyl isocyanate to be used as the chiral stationary phase (CSP) in high-performance liquid chromatography (HPLC). The structures of the CDMPC derivatives were investigated by infrared spectroscopy (IR), ¹H-NMR, circular dichroism (CD) and size exclusion chromatography (SEC), and the DPs of the derivatives estimated by SEC agreed with those estimated by ¹H-NMR. After coating the derivatives on silica gel, their chiral recognition abilities were evaluated using eight racemates under a normal phase condition with a hexane-2-propanol (99/1) mixture as an eluent. The chiral recognition abilities of 7- and 11-mers, particularly the former, were lower than those of the higher oligomers from DP 18 to 52, which had rather similar abilities to that of 124-mer, although the abilities depended on the racemates. DP 18 seems to be sufficient for CDMPC to exhibit chiral recognition similar to that of the CDMPC with larger DPs.</div></front></TEI></pubmed></double></record>Pour manipuler ce document sous Unix (Dilib)
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