| Hydrolysis of the GlcNAc oxazoline: deamidation and acyl rearrangement. | |
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MedLine Citation:
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PMID: 8548785 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The specific deamidation of 2-acetamido-1,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose is achieved by p-toluenesulfonic acid-promoted hydrolysis of 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)-[2,1 -d]-2- oxazoline 2 to give quantitative formation of the 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-alpha-D-glucopyranose p-toluenesulfonate (5d). This two-step procedure provides an amino sugar which may be readily acylated to give novel glycoconjugates. Alternatively, base-catalyzed O-1-->N-2 acyl rearrangement of the amino tosylate 5d gives the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranose 4 as a 9:1 mixture of alpha and beta anomers. Thus, hydrolysis of GlcNAc oxazoline 2 gives the amino-ester 5 as the kinetic product and the amido-alcohol 4 as the thermodynamic product. |
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Authors:
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R Jha; J T Davis |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Carbohydrate research Volume: 277 ISSN: 0008-6215 ISO Abbreviation: Carbohydr. Res. Publication Date: 1995 Nov |
Date Detail:
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Created Date: 1996-02-21 Completed Date: 1996-02-21 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 0043535 Medline TA: Carbohydr Res Country: NETHERLANDS |
Other Details:
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Languages: eng Pagination: 125-34 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Biochemistry, University of Maryland, College Park 20742, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acylation Carbohydrate Sequence Glucose / analogs & derivatives*, chemistry Glycoconjugates / chemistry* Hydrolysis Magnetic Resonance Spectroscopy Models, Chemical Models, Molecular Molecular Sequence Data Molecular Structure Oxazoles / chemistry* |
| Chemical | |
Reg. No./Substance:
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0/2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxyglucopyrano)(2,1-d)-2-oxazoline; 0/Glycoconjugates; 0/Oxazoles; 50-99-7/Glucose |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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