Literature DB >> 1148272

Cell-surface carbohydrates and their interactions. I. NMR or N-acetyl neuraminic acid.

E B Brown, W S Brey, W Weltner.   

Abstract

1. The proton nuclear magnetic resonance spectrum of the sialic acid N-acetyl neuraminic acid was measured and completely assigned. The coupling constants for interactions between protons are obtained and the assignments checked by calculating the observed line intensities. 2. It was verified that the pyranose ring exists in the 1C (1-C4) conformation as the alph-D anomer and no mutarotation was detectable. Coupling constants for the glycerol side chain were interpreted to yield its most likely conformation.

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Year:  1975        PMID: 1148272     DOI: 10.1016/0304-4165(75)90218-4

Source DB:  PubMed          Journal:  Biochim Biophys Acta        ISSN: 0006-3002


  11 in total

1.  Modeling ganglioside headgroups by conformational analysis and molecular dynamics.

Authors:  P Brocca; A Bernardi; L Raimondi; S Sonnino
Journal:  Glycoconj J       Date:  2000-05       Impact factor: 2.916

2.  Stereoselective Synthesis of the Equatorial Glycosides of Legionaminic Acid.

Authors:  Oskar Popik; Bibek Dhakal; David Crich
Journal:  J Org Chem       Date:  2017-06-02       Impact factor: 4.354

3.  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.

Authors:  Mohammed Hawsawi; Anura Wickramasinghe; David Crich
Journal:  J Org Chem       Date:  2019-10-29       Impact factor: 4.354

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.

Authors:  Bibek Dhakal; Szymon Buda; David Crich
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
Journal:  J Am Chem Soc       Date:  2018-10-25       Impact factor: 15.419

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

Authors:  Szymon Buda; David Crich
Journal:  J Am Chem Soc       Date:  2016-01-15       Impact factor: 15.419

7.  The solution conformation of sialyl-alpha (2----6)-lactose studied by modern NMR techniques and Monte Carlo simulations.

Authors:  L Poppe; R Stuike-Prill; B Meyer; H van Halbeek
Journal:  J Biomol NMR       Date:  1992-03       Impact factor: 2.835

8.  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

9.  GLYCAM06: a generalizable biomolecular force field. Carbohydrates.

Authors:  Karl N Kirschner; Austin B Yongye; Sarah M Tschampel; Jorge González-Outeiriño; Charlisa R Daniels; B Lachele Foley; Robert J Woods
Journal:  J Comput Chem       Date:  2008-03       Impact factor: 3.376

Review 10.  Exploration of the Sialic Acid World.

Authors:  Roland Schauer; Johannis P Kamerling
Journal:  Adv Carbohydr Chem Biochem       Date:  2018-11-28       Impact factor: 12.200

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