Enantioseparation Using Cellulose Tris(3,5-dimethylphenylcarbamate) as Chiral Stationary Phase for HPLC: Influence of Molecular Weight of Cellulose.
Identifieur interne : 000E97 ( PubMed/Corpus ); précédent : 000E96; suivant : 000E98Enantioseparation 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 (Basel, Switzerland) [ 1420-3049 ] ; 2016.
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.
DOI: 10.3390/molecules21111484
PubMed: 27834832
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Kamigaito</name><affiliation><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. kamigait@apchem.nagoya-u.ac.jp.</nlm:affiliation></affiliation></author><author><name sortKey="Gao, Yuan" sort="Gao, Yuan" uniqKey="Gao Y" first="Yuan" last="Gao">Yuan Gao</name><affiliation><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></affiliation></author><author><name sortKey="Shen, Jun" sort="Shen, Jun" uniqKey="Shen J" first="Jun" last="Shen">Jun Shen</name><affiliation><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></affiliation></author><author><name sortKey="Okamoto, Yoshio" sort="Okamoto, Yoshio" uniqKey="Okamoto Y" first="Yoshio" last="Okamoto">Yoshio Okamoto</name><affiliation><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. okamoto@apchem.nagoya-u.ac.jp.</nlm:affiliation></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></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><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. column_okd@yahoo.co.jp.</nlm:affiliation></affiliation></author><author><name sortKey="Yamamoto, Chiyo" sort="Yamamoto, Chiyo" uniqKey="Yamamoto C" first="Chiyo" last="Yamamoto">Chiyo Yamamoto</name><affiliation><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. chiyo@chem.suzuka-ct.ac.jp.</nlm:affiliation></affiliation></author><author><name sortKey="Kamigaito, Masami" sort="Kamigaito, Masami" uniqKey="Kamigaito M" first="Masami" last="Kamigaito">Masami Kamigaito</name><affiliation><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. kamigait@apchem.nagoya-u.ac.jp.</nlm:affiliation></affiliation></author><author><name sortKey="Gao, Yuan" sort="Gao, Yuan" uniqKey="Gao Y" first="Yuan" last="Gao">Yuan Gao</name><affiliation><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></affiliation></author><author><name sortKey="Shen, Jun" sort="Shen, Jun" uniqKey="Shen J" first="Jun" last="Shen">Jun Shen</name><affiliation><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></affiliation></author><author><name sortKey="Okamoto, Yoshio" sort="Okamoto, Yoshio" uniqKey="Okamoto Y" first="Yoshio" last="Okamoto">Yoshio Okamoto</name><affiliation><nlm:affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. okamoto@apchem.nagoya-u.ac.jp.</nlm:affiliation></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="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="methods" xml:lang="en"><term>Chromatography, High Pressure Liquid</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Hydrolysis</term><term>Molecular Structure</term><term>Molecular Weight</term><term>Stereoisomerism</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><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">27834832</PMID><DateCompleted><Year>2017</Year><Month>04</Month><Day>13</Day></DateCompleted><DateRevised><Year>2020</Year><Month>02</Month><Day>25</Day></DateRevised><Article PubModel="Electronic"><Journal><ISSN IssnType="Electronic">1420-3049</ISSN><JournalIssue CitedMedium="Internet"><Volume>21</Volume><Issue>11</Issue><PubDate><Year>2016</Year><Month>Nov</Month><Day>08</Day></PubDate></JournalIssue><Title>Molecules (Basel, Switzerland)</Title><ISOAbbreviation>Molecules</ISOAbbreviation></Journal><ArticleTitle>Enantioseparation Using Cellulose Tris(3,5-dimethylphenylcarbamate) as Chiral Stationary Phase for HPLC: Influence of Molecular Weight of Cellulose.</ArticleTitle><ELocationID EIdType="pii" ValidYN="Y">E1484</ELocationID><Abstract><AbstractText>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.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Okada</LastName><ForeName>Yuji</ForeName><Initials>Y</Initials><AffiliationInfo><Affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. column_okd@yahoo.co.jp.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Yamamoto</LastName><ForeName>Chiyo</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. chiyo@chem.suzuka-ct.ac.jp.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kamigaito</LastName><ForeName>Masami</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. kamigait@apchem.nagoya-u.ac.jp.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gao</LastName><ForeName>Yuan</ForeName><Initials>Y</Initials><AffiliationInfo><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.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Shen</LastName><ForeName>Jun</ForeName><Initials>J</Initials><AffiliationInfo><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.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Okamoto</LastName><ForeName>Yoshio</ForeName><Initials>Y</Initials><AffiliationInfo><Affiliation>Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan. okamoto@apchem.nagoya-u.ac.jp.</Affiliation></AffiliationInfo><AffiliationInfo><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. okamoto@apchem.nagoya-u.ac.jp.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>11</Month><Day>08</Day></ArticleDate></Article><MedlineJournalInfo><Country>Switzerland</Country><MedlineTA>Molecules</MedlineTA><NlmUniqueID>100964009</NlmUniqueID><ISSNLinking>1420-3049</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D048448">Phenylcarbamates</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010756">Phosphoric Acids</NameOfSubstance></Chemical><Chemical><RegistryNumber>110735-13-2</RegistryNumber><NameOfSubstance UI="C065943">cellulose tris-3,5-dimethylphenyl-carbamate</NameOfSubstance></Chemical><Chemical><RegistryNumber>9004-34-6</RegistryNumber><NameOfSubstance UI="D002482">Cellulose</NameOfSubstance></Chemical><Chemical><RegistryNumber>E4GA8884NN</RegistryNumber><NameOfSubstance UI="C030242">phosphoric acid</NameOfSubstance></Chemical><Chemical><RegistryNumber>OP1R32D61U</RegistryNumber><NameOfSubstance 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Weight</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D048448" MajorTopicYN="N">Phenylcarbamates</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010756" MajorTopicYN="N">Phosphoric Acids</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="Y">chiral separation</Keyword><Keyword MajorTopicYN="Y">enantiomer</Keyword><Keyword MajorTopicYN="Y">phenylcarbamate</Keyword><Keyword MajorTopicYN="Y">polysaccharide</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2016</Year><Month>10</Month><Day>06</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2016</Year><Month>11</Month><Day>01</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2016</Year><Month>11</Month><Day>02</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>11</Month><Day>12</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>11</Month><Day>12</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2017</Year><Month>4</Month><Day>14</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>epublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">27834832</ArticleId><ArticleId IdType="pii">molecules21111484</ArticleId><ArticleId IdType="doi">10.3390/molecules21111484</ArticleId><ArticleId IdType="pmc">PMC6273561</ArticleId></ArticleIdList><ReferenceList><Reference><Citation>J Chromatogr A. 2012 Dec 21;1269:26-51</Citation><ArticleIdList><ArticleId 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