Chemoenzymatic synthesis of stable isotope labeled UDP-N-[2H]-acetyl-glucosamine and [2H]-acetyl-chitooligosaccharides.
Identifieur interne : 002152 ( PubMed/Checkpoint ); précédent : 002151; suivant : 002153Chemoenzymatic synthesis of stable isotope labeled UDP-N-[2H]-acetyl-glucosamine and [2H]-acetyl-chitooligosaccharides.
Auteurs : Hubert F. Becker [France] ; Annie Thellend ; Annie Piffeteau ; Anne Vidal-CrosSource :
- Glycoconjugate journal [ 0282-0080 ] ; 2006.
Descripteurs français
- KwdFr :
- Acétylation, Chitine (métabolisme), Chitine synthase (analyse), Chitine synthase (métabolisme), Chromatographie sur couche mince, Deutérium (métabolisme), Oligosaccharides (métabolisme), Spectrométrie de masse ESI, Structure moléculaire, Séquence glucidique, Uridine diphosphate N-acétylglucosamine (), Uridine diphosphate N-acétylglucosamine (synthèse chimique).
- MESH :
- analyse : Chitine synthase.
- métabolisme : Chitine, Chitine synthase, Deutérium, Oligosaccharides.
- synthèse chimique : Uridine diphosphate N-acétylglucosamine.
- Acétylation, Chromatographie sur couche mince, Spectrométrie de masse ESI, Structure moléculaire, Séquence glucidique, Uridine diphosphate N-acétylglucosamine.
English descriptors
- KwdEn :
- Acetylation, Carbohydrate Sequence, Chitin (metabolism), Chitin Synthase (analysis), Chitin Synthase (metabolism), Chromatography, Thin Layer, Deuterium (metabolism), Molecular Structure, Oligosaccharides (metabolism), Spectrometry, Mass, Electrospray Ionization, Uridine Diphosphate N-Acetylglucosamine (chemical synthesis), Uridine Diphosphate N-Acetylglucosamine (chemistry).
- MESH :
- chemical , analysis : Chitin Synthase.
- chemical , chemical synthesis : Uridine Diphosphate N-Acetylglucosamine.
- chemical , chemistry : Uridine Diphosphate N-Acetylglucosamine.
- chemical , metabolism : Chitin, Chitin Synthase, Deuterium, Oligosaccharides.
- Acetylation, Carbohydrate Sequence, Chromatography, Thin Layer, Molecular Structure, Spectrometry, Mass, Electrospray Ionization.
Abstract
Labeled UDP-GlcNAc and chitooligosaccharides should be powerful tools for studies of N-acetylglucosaminyltransferase such as chitin synthases. We describe here a rapid, inexpensive and a common strategie for the chemoenzymatic synthesis of uridine 5'-diphospho-N-[(2)H]-acetyl-glucosamine and the chemical preparation of N-[(2)H]-acetyl chitooligosaccharides (from 2 to 5 mers). Deuterated UDP-GlcNAc analogue was tested as chitin synthase substrate and it exhibited an incorporation level in chitin as the natural substrate. Deuterium labeling of carbohydrates present different advantages: it is a stable isotope and allows glycosyltransferase mechanism studies by a mass spectrometry approach.
DOI: 10.1007/s10719-006-9018-8
PubMed: 17123165
Affiliations:
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Becker</name><affiliation wicri:level="4"><nlm:affiliation>Synthèse, Structure et Fonction de Molécules Bioactives UMR7613, Université Pierre et Marie Curie, Tour 44-45, 3ème étage, 4 place Jussieu, 75252, Paris, France. hbecker@moka.ccr.jussieu.fr</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Synthèse, Structure et Fonction de Molécules Bioactives UMR7613, Université Pierre et Marie Curie, Tour 44-45, 3ème étage, 4 place Jussieu, 75252, Paris</wicri:regionArea><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Paris</settlement></placeName><orgName type="university">Université Pierre-et-Marie-Curie</orgName></affiliation></author><author><name sortKey="Thellend, Annie" sort="Thellend, Annie" uniqKey="Thellend A" first="Annie" last="Thellend">Annie Thellend</name></author><author><name sortKey="Piffeteau, Annie" sort="Piffeteau, Annie" uniqKey="Piffeteau A" first="Annie" last="Piffeteau">Annie Piffeteau</name></author><author><name sortKey="Vidal Cros, Anne" sort="Vidal Cros, Anne" uniqKey="Vidal Cros A" first="Anne" last="Vidal-Cros">Anne Vidal-Cros</name></author></analytic><series><title level="j">Glycoconjugate journal</title><idno type="ISSN">0282-0080</idno><imprint><date when="2006" type="published">2006</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Acetylation</term><term>Carbohydrate Sequence</term><term>Chitin (metabolism)</term><term>Chitin Synthase (analysis)</term><term>Chitin Synthase (metabolism)</term><term>Chromatography, Thin Layer</term><term>Deuterium (metabolism)</term><term>Molecular Structure</term><term>Oligosaccharides (metabolism)</term><term>Spectrometry, Mass, Electrospray Ionization</term><term>Uridine Diphosphate N-Acetylglucosamine (chemical synthesis)</term><term>Uridine Diphosphate N-Acetylglucosamine (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acétylation</term><term>Chitine (métabolisme)</term><term>Chitine synthase (analyse)</term><term>Chitine synthase (métabolisme)</term><term>Chromatographie sur couche mince</term><term>Deutérium (métabolisme)</term><term>Oligosaccharides (métabolisme)</term><term>Spectrométrie de masse ESI</term><term>Structure moléculaire</term><term>Séquence glucidique</term><term>Uridine diphosphate N-acétylglucosamine ()</term><term>Uridine diphosphate N-acétylglucosamine (synthèse chimique)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analysis" xml:lang="en"><term>Chitin Synthase</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Uridine Diphosphate N-Acetylglucosamine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Uridine Diphosphate N-Acetylglucosamine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Chitin</term><term>Chitin Synthase</term><term>Deuterium</term><term>Oligosaccharides</term></keywords><keywords scheme="MESH" qualifier="analyse" xml:lang="fr"><term>Chitine synthase</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Chitine</term><term>Chitine synthase</term><term>Deutérium</term><term>Oligosaccharides</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Uridine diphosphate N-acétylglucosamine</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Acetylation</term><term>Carbohydrate Sequence</term><term>Chromatography, Thin Layer</term><term>Molecular Structure</term><term>Spectrometry, Mass, Electrospray Ionization</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Acétylation</term><term>Chromatographie sur couche mince</term><term>Spectrométrie de masse ESI</term><term>Structure moléculaire</term><term>Séquence glucidique</term><term>Uridine diphosphate N-acétylglucosamine</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Labeled UDP-GlcNAc and chitooligosaccharides should be powerful tools for studies of N-acetylglucosaminyltransferase such as chitin synthases. We describe here a rapid, inexpensive and a common strategie for the chemoenzymatic synthesis of uridine 5'-diphospho-N-[(2)H]-acetyl-glucosamine and the chemical preparation of N-[(2)H]-acetyl chitooligosaccharides (from 2 to 5 mers). Deuterated UDP-GlcNAc analogue was tested as chitin synthase substrate and it exhibited an incorporation level in chitin as the natural substrate. Deuterium labeling of carbohydrates present different advantages: it is a stable isotope and allows glycosyltransferase mechanism studies by a mass spectrometry approach.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">17123165</PMID><DateCompleted><Year>2007</Year><Month>03</Month><Day>15</Day></DateCompleted><DateRevised><Year>2018</Year><Month>11</Month><Day>13</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Print">0282-0080</ISSN><JournalIssue CitedMedium="Print"><Volume>23</Volume><Issue>9</Issue><PubDate><Year>2006</Year><Month>Dec</Month></PubDate></JournalIssue><Title>Glycoconjugate journal</Title><ISOAbbreviation>Glycoconj. J.</ISOAbbreviation></Journal><ArticleTitle>Chemoenzymatic synthesis of stable isotope labeled UDP-N-[2H]-acetyl-glucosamine and [2H]-acetyl-chitooligosaccharides.</ArticleTitle><Pagination><MedlinePgn>687-92</MedlinePgn></Pagination><Abstract><AbstractText>Labeled UDP-GlcNAc and chitooligosaccharides should be powerful tools for studies of N-acetylglucosaminyltransferase such as chitin synthases. We describe here a rapid, inexpensive and a common strategie for the chemoenzymatic synthesis of uridine 5'-diphospho-N-[(2)H]-acetyl-glucosamine and the chemical preparation of N-[(2)H]-acetyl chitooligosaccharides (from 2 to 5 mers). Deuterated UDP-GlcNAc analogue was tested as chitin synthase substrate and it exhibited an incorporation level in chitin as the natural substrate. Deuterium labeling of carbohydrates present different advantages: it is a stable isotope and allows glycosyltransferase mechanism studies by a mass spectrometry approach.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Becker</LastName><ForeName>Hubert F</ForeName><Initials>HF</Initials><AffiliationInfo><Affiliation>Synthèse, Structure et Fonction de Molécules Bioactives UMR7613, Université Pierre et Marie Curie, Tour 44-45, 3ème étage, 4 place Jussieu, 75252, Paris, France. hbecker@moka.ccr.jussieu.fr</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Thellend</LastName><ForeName>Annie</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Piffeteau</LastName><ForeName>Annie</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Vidal-Cros</LastName><ForeName>Anne</ForeName><Initials>A</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2006</Year><Month>11</Month><Day>23</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Glycoconj J</MedlineTA><NlmUniqueID>8603310</NlmUniqueID><ISSNLinking>0282-0080</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009844">Oligosaccharides</NameOfSubstance></Chemical><Chemical><RegistryNumber>1398-61-4</RegistryNumber><NameOfSubstance UI="D002686">Chitin</NameOfSubstance></Chemical><Chemical><RegistryNumber>528-04-1</RegistryNumber><NameOfSubstance UI="D014537">Uridine Diphosphate N-Acetylglucosamine</NameOfSubstance></Chemical><Chemical><RegistryNumber>AR09D82C7G</RegistryNumber><NameOfSubstance UI="D003903">Deuterium</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.4.1.16</RegistryNumber><NameOfSubstance UI="D002687">Chitin 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