Literature DB >> 3594474

On the side-chain conformation of N-acetylneuraminic acid and its epimers at C-7, C-8, and C-7,8.

R Christian, G Schulz, H H Brandstetter, E Zbiral.   

Abstract

The side-chain conformation of N-acetylneuraminic acid and analogs has been studied by n.m.r. spectroscopy. The results of the 1H-, 13C-n.m.r.-, and 1H-nuclear-Overhauser-enhancement measurements were used to distinguish between different local-minima conformations suggested by hard-sphere calculations. Attempts were made to correlate the major conformation determined for each compound with the behavior towards activation with N-acetylneuraminic acid-CMP-synthetase.

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Year:  1987        PMID： 3594474     DOI： 10.1016/0008-6215(87)80195-7

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  11 in total

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2.  Use of Phenols as Nucleophiles in the Zbiral Oxidative Deamination of N-Acetyl Neuraminic Acid: Isolation and Characterization of Tricyclic 3-Keto-2-deoxy-nonulosonic Acid (KDN) Derivatives via an Intermediate Vinyl Diazonium Ion.

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3.  Computational studies of sialyllactones: methods and uses.

Authors:  A L Parrill; N Mamuya; D P Dolata; J Gervay
Journal:  Glycoconj J       Date:  1997-06       Impact factor: 2.916

4.  Stereoselective Synthesis of 5-epi-α-Sialosides Related to the Pseudaminic Acid Glycosides. Reassessment of the Stereoselectivity of the 5-Azido-5-deacetamidosialyl Thioglycosides and Use of Triflate as Nucleophile in the Zbiral Deamination of Sialic Acids.

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Journal:  J Org Chem       Date:  2016-11-10       Impact factor: 4.354

5.  Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups.

Authors:  Bibek Dhakal; David Crich
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6.  Elucidation of the topological parameters of N-acetylneuraminic acid and some analogues involved in their interaction with the N-acetylneuraminate lyase from Clostridium perfringens.

Authors:  E Zbiral; R G Kleineidam; E Schreiner; M Hartmann; R Christian; R Schauer
Journal:  Biochem J       Date:  1992-03-01       Impact factor: 3.857

7.  Oxidative Deamination of N-Acetyl Neuraminic Acid: Substituent Effects and Mechanism.

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Journal:  J Am Chem Soc       Date:  2016-01-15       Impact factor: 15.419

8.  Application of 2D and 3D NMR experiments to the conformational study of a diantennary oligosaccharide.

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Journal:  J Biomol NMR       Date:  1992-05       Impact factor: 2.835

9.  Influence of side chain conformation and configuration on glycosyl donor reactivity and selectivity as illustrated by sialic acid donors epimeric at the 7-position.

Authors:  Pavan K Kancharla; David Crich
Journal:  J Am Chem Soc       Date:  2013-12-09       Impact factor: 15.419

10.  Synthesis of Conformationally-Locked cis- and trans-Bicyclo[4.4.0] Mono-, Di-, and Trioxadecane Modifications of Galacto- and Glucopyranose; Experimental Limiting 3JH,H Coupling Constants for the Estimation of Carbohydrate Side Chain Populations and Beyond.

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Journal:  J Org Chem       Date:  2018-01-03       Impact factor: 4.354
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