Journal ArticleDOI
A simple method to determine the anomeric configuration of sialic acid and its derivatives by 13C-NMR
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TLDR
In this article, the anomeric configuration of sialic acid and its derivatives was determined on the basis of the coupling pattern of C-1 in the gated proton-decoupled or selective proton decoupled 13C-NMR spectra.About:
This article is published in Tetrahedron Letters.The article was published on 1988-01-01. It has received 115 citations till now. The article focuses on the topics: Anomer & Singlet state.read more
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Book ChapterDOI
Chapter 11 – Chemistry, biochemistry and biology of sialic acids ☆
Journal ArticleDOI
Glycosidation of sialic acid
Kaoru Okamoto,Toshio Goto +1 more
TL;DR: Enzymic and synthetic approaches to the glycosidation of sialic acid by new methodologies are discussed, which aim to clarify their vital functions and identify the most difficult problem remaining.
Journal ArticleDOI
Highly Alpha‐Selective Sialyl Phosphate Donors for Efficient Preparation of Natural Sialosides
Che-Hsiung Hsu,Kuo-Ching Chu,Yih-Shyan Lin,Jeng-Liang Han,Yu-Shiang Peng,Chien-Tai Ren,Chung-Yi Wu,Chi-Huey Wong,Chi-Huey Wong +8 more
TL;DR: A new sialylation reagent 1 is reported that employs an N-acetyl-5-N,4-O-carbonyl protection with dibutyl phosphate as the leaving group and the new donor was applied to develop efficient strategies to use to create natural sialosides.
References
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Journal ArticleDOI
Synthese anomerer Sialinsäure-methylketoside
TL;DR: In this article, the Acetochlor-Verbindung des Lactaminsaure-methylesters wurde nach Koenigs-Knorr ein Methylketosidmethylter von [α]: −6° erhalten, der von Neuraminidase quantitativ gespalten wird.
Journal ArticleDOI
Configuration of the ketosidic bond of sialic acid.
Robert K. Yu,Robert W. Ledeen +1 more
TL;DR: The configuration of the ketosidic bond of sialic acid in naturally occurring substances, such as gangliosides, glycoproteins, and the like, is therefore the less stable anomer I, with the keto-d configuration equatorial and the carboxyl group axial to the pyranoid ring.
Journal ArticleDOI
1H-NMR studies at N-acetyl-D-neuraminic acid ketosides for the determination of the anomeric configuration II.
TL;DR: In this paper, the 1 H-nmr signal of the equatorially orientated protons at C-3 of N-acetyl-D-neuraminic acid and its derivatives shows a quite characteristic dependence on the anomeric configurations.
Journal ArticleDOI
Functionalization of 2-deoxy-2,3-dehydro-N-acetylneuraminic acid methyl ester.
TL;DR: In this article, the acetyl protected 2-deoxy-2,3-dehydroneuraminic acid methyl ester was functionalized by modifying its 2-3-double bond to convert it into new glycosyl donors such as 2, 3-dibromo-, 2.3-epoxy-, and 2-halo-3,hydroxyneuraminaic acid derivatives.
Journal ArticleDOI
Synthese eines trisaccharides aus N-acetylneuraminsäure und N-acetyllactosamin
Hans Paulsen,Holger Tietz +1 more
TL;DR: A deblocking sequence, consisting of hydrogen sulfide reduction, acetylation, deacetylation and ester hydrolysis, and hydrogenolysis, led to the deblocked O-(5-acetamido-3,5-dideoxy-d -glycero-α- d -galacto-2-nonulopyranosylonic acid)-(2→6)-linked compound.
Related Papers (5)
O-Sialylation with N-Acetyl-5-N,4-O-Carbonyl-Protected Thiosialoside Donors in Dichloromethane: Facile and Selective Cleavage of the Oxazolidinone Ring
David Crich,Wenju Li +1 more