Evidence of nanotubular self-organization in solution and solid states of heterochiral cyclo 1:1 [α/α-N(α)-Bn-hydrazino]mers series.
Identifieur interne : 001553 ( PubMed/Checkpoint ); précédent : 001552; suivant : 001554Evidence of nanotubular self-organization in solution and solid states of heterochiral cyclo 1:1 [α/α-N(α)-Bn-hydrazino]mers series.
Auteurs : Ralph-Olivier Moussodia [France] ; Samir Acherar [France] ; Eugénie Romero [France] ; Claude Didierjean [France] ; Brigitte Jamart-Grégoire [France]Source :
- The Journal of organic chemistry [ 1520-6904 ] ; 2015.
Descripteurs français
- KwdFr :
- MESH :
- analogues et dérivés : Alanine.
- synthèse chimique : Alanine.
- Alanine, Cristallographie aux rayons X, Cyclisation, Modèles moléculaires, Nanotubes, Solutions.
English descriptors
- KwdEn :
- MESH :
- chemical , analogs & derivatives : Alanine.
- chemical , chemical synthesis : Alanine.
- chemical , chemistry : Alanine.
- chemistry : Nanotubes.
- Crystallography, X-Ray, Cyclization, Models, Molecular, Solutions.
Abstract
The cyclization of heterochiral 1:1 [α/α-N(α)-Bn-hydrazino]mers leads to the corresponding cyclotetramer and cyclohexamer 3 and 4. X-ray crystallographic analysis of 3 unveils its ability to self-assemble into nanotubular structures. Further experiments conducted in the solid state through SEM analyses demonstrate the capability of 3 and 4 to form aerogels consisting of a network of nontwisted fibers, thus confirming the presence of self-organization within this series of mixed-hydrazinopeptides. Subsequent FTIR and NMR studies demonstrate the presence of an equilibrium between monomeric (intramolecular H-bonds) and nanotubular (intermolecular H-bonds) forms in solution. This equilibrium can be modified by varying the solvent.
DOI: 10.1021/jo502684g
PubMed: 25734802
Affiliations:
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wicri:level="3"><nlm:affiliation>†Laboratoire de Chimie Physique Macromoléculaire (LCPM), Université de Lorraine-CNRS, UMR 7375, 1 rue Grandville, BP 20451, 54001 Nancy cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>†Laboratoire de Chimie Physique Macromoléculaire (LCPM), Université de Lorraine-CNRS, UMR 7375, 1 rue Grandville, BP 20451, 54001 Nancy cedex</wicri:regionArea><placeName><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Lorraine (région)</region><settlement type="city">Nancy</settlement></placeName></affiliation></author><author><name sortKey="Didierjean, Claude" sort="Didierjean, Claude" uniqKey="Didierjean C" first="Claude" last="Didierjean">Claude Didierjean</name><affiliation wicri:level="3"><nlm:affiliation>‡Laboratoire de Crystallographie, Résonance Magnétique et Modélisations (CRM2), Université de Lorraine-CNRS, UMR 7036, Faculté des Sciences et Technologies, BP 20239, 54506 Vandœuvre-lès-Nancy cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>‡Laboratoire de Crystallographie, Résonance Magnétique et Modélisations (CRM2), Université de Lorraine-CNRS, UMR 7036, Faculté des Sciences et Technologies, BP 20239, 54506 Vandœuvre-lès-Nancy cedex</wicri:regionArea><placeName><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Lorraine (région)</region><settlement type="city">Vandœuvre-lès-Nancy</settlement></placeName></affiliation></author><author><name sortKey="Jamart Gregoire, Brigitte" sort="Jamart Gregoire, Brigitte" uniqKey="Jamart Gregoire B" first="Brigitte" last="Jamart-Grégoire">Brigitte Jamart-Grégoire</name><affiliation wicri:level="3"><nlm:affiliation>†Laboratoire de Chimie Physique Macromoléculaire (LCPM), Université de Lorraine-CNRS, UMR 7375, 1 rue Grandville, BP 20451, 54001 Nancy cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>†Laboratoire de Chimie Physique Macromoléculaire (LCPM), Université de Lorraine-CNRS, UMR 7375, 1 rue Grandville, BP 20451, 54001 Nancy cedex</wicri:regionArea><placeName><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Lorraine (région)</region><settlement type="city">Nancy</settlement></placeName></affiliation></author></analytic><series><title level="j">The Journal of organic chemistry</title><idno type="eISSN">1520-6904</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Alanine (analogs & derivatives)</term><term>Alanine (chemical synthesis)</term><term>Alanine (chemistry)</term><term>Crystallography, X-Ray</term><term>Cyclization</term><term>Models, Molecular</term><term>Nanotubes (chemistry)</term><term>Solutions</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Alanine ()</term><term>Alanine (analogues et dérivés)</term><term>Alanine (synthèse chimique)</term><term>Cristallographie aux rayons X</term><term>Cyclisation</term><term>Modèles moléculaires</term><term>Nanotubes ()</term><term>Solutions</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Alanine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Alanine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Alanine</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Alanine</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Nanotubes</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Alanine</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Crystallography, X-Ray</term><term>Cyclization</term><term>Models, Molecular</term><term>Solutions</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Alanine</term><term>Cristallographie aux rayons X</term><term>Cyclisation</term><term>Modèles moléculaires</term><term>Nanotubes</term><term>Solutions</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The cyclization of heterochiral 1:1 [α/α-N(α)-Bn-hydrazino]mers leads to the corresponding cyclotetramer and cyclohexamer 3 and 4. X-ray crystallographic analysis of 3 unveils its ability to self-assemble into nanotubular structures. Further experiments conducted in the solid state through SEM analyses demonstrate the capability of 3 and 4 to form aerogels consisting of a network of nontwisted fibers, thus confirming the presence of self-organization within this series of mixed-hydrazinopeptides. Subsequent FTIR and NMR studies demonstrate the presence of an equilibrium between monomeric (intramolecular H-bonds) and nanotubular (intermolecular H-bonds) forms in solution. This equilibrium can be modified by varying the solvent. </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">25734802</PMID><DateCompleted><Year>2015</Year><Month>12</Month><Day>07</Day></DateCompleted><DateRevised><Year>2015</Year><Month>03</Month><Day>20</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6904</ISSN><JournalIssue CitedMedium="Internet"><Volume>80</Volume><Issue>6</Issue><PubDate><Year>2015</Year><Month>Mar</Month><Day>20</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Evidence of nanotubular self-organization in solution and solid states of heterochiral cyclo 1:1 [α/α-N(α)-Bn-hydrazino]mers series.</ArticleTitle><Pagination><MedlinePgn>3022-9</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jo502684g</ELocationID><Abstract><AbstractText>The cyclization of heterochiral 1:1 [α/α-N(α)-Bn-hydrazino]mers leads to the corresponding cyclotetramer and cyclohexamer 3 and 4. X-ray crystallographic analysis of 3 unveils its ability to self-assemble into nanotubular structures. Further experiments conducted in the solid state through SEM analyses demonstrate the capability of 3 and 4 to form aerogels consisting of a network of nontwisted fibers, thus confirming the presence of self-organization within this series of mixed-hydrazinopeptides. Subsequent FTIR and NMR studies demonstrate the presence of an equilibrium between monomeric (intramolecular H-bonds) and nanotubular (intermolecular H-bonds) forms in solution. This equilibrium can be modified by varying the solvent. </AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Moussodia</LastName><ForeName>Ralph-Olivier</ForeName><Initials>RO</Initials><AffiliationInfo><Affiliation>†Laboratoire de Chimie Physique Macromoléculaire (LCPM), Université de Lorraine-CNRS, UMR 7375, 1 rue Grandville, BP 20451, 54001 Nancy cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Acherar</LastName><ForeName>Samir</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>†Laboratoire de Chimie Physique Macromoléculaire (LCPM), Université de Lorraine-CNRS, UMR 7375, 1 rue Grandville, BP 20451, 54001 Nancy cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Romero</LastName><ForeName>Eugénie</ForeName><Initials>E</Initials><AffiliationInfo><Affiliation>†Laboratoire de Chimie Physique Macromoléculaire (LCPM), Université de Lorraine-CNRS, UMR 7375, 1 rue Grandville, BP 20451, 54001 Nancy cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Didierjean</LastName><ForeName>Claude</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>‡Laboratoire de Crystallographie, Résonance Magnétique et Modélisations (CRM2), Université de Lorraine-CNRS, UMR 7036, Faculté des Sciences et Technologies, BP 20239, 54506 Vandœuvre-lès-Nancy cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Jamart-Grégoire</LastName><ForeName>Brigitte</ForeName><Initials>B</Initials><AffiliationInfo><Affiliation>†Laboratoire de Chimie Physique Macromoléculaire (LCPM), Université de Lorraine-CNRS, UMR 7375, 1 rue Grandville, BP 20451, 54001 Nancy cedex, France.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2015</Year><Month>03</Month><Day>11</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D012996">Solutions</NameOfSubstance></Chemical><Chemical><RegistryNumber>OF5P57N2ZX</RegistryNumber><NameOfSubstance UI="D000409">Alanine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000409" MajorTopicYN="N">Alanine</DescriptorName><QualifierName UI="Q000031" MajorTopicYN="N">analogs & derivatives</QualifierName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D018360" MajorTopicYN="N">Crystallography, X-Ray</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D003500" MajorTopicYN="N">Cyclization</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008958" MajorTopicYN="N">Models, Molecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D043942" MajorTopicYN="N">Nanotubes</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012996" MajorTopicYN="N">Solutions</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2015</Year><Month>3</Month><Day>4</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2015</Year><Month>3</Month><Day>4</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2015</Year><Month>12</Month><Day>15</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">25734802</ArticleId><ArticleId IdType="doi">10.1021/jo502684g</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>France</li></country><region><li>Grand Est</li><li>Lorraine (région)</li></region><settlement><li>Nancy</li><li>Vandœuvre-lès-Nancy</li></settlement></list><tree><country name="France"><region name="Grand Est"><name sortKey="Moussodia, Ralph Olivier" sort="Moussodia, Ralph Olivier" uniqKey="Moussodia R" first="Ralph-Olivier" last="Moussodia">Ralph-Olivier Moussodia</name></region><name sortKey="Acherar, Samir" sort="Acherar, Samir" uniqKey="Acherar S" first="Samir" last="Acherar">Samir Acherar</name><name sortKey="Didierjean, Claude" sort="Didierjean, Claude" uniqKey="Didierjean C" first="Claude" last="Didierjean">Claude Didierjean</name><name sortKey="Jamart Gregoire, Brigitte" sort="Jamart Gregoire, Brigitte" uniqKey="Jamart Gregoire B" first="Brigitte" last="Jamart-Grégoire">Brigitte Jamart-Grégoire</name><name sortKey="Romero, Eugenie" sort="Romero, Eugenie" uniqKey="Romero E" first="Eugénie" last="Romero">Eugénie Romero</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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