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Studies on sialic acids I. Determination of anomeric configuration of neuraminic acid derivatives by circular dichroism

โœ Scribed by Haruo Ogura; Kimio Furuhata


Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
205 KB
Volume
22
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


CD spectra were recorded for D-neuraminic acid, and the band was attributed to the acetamido wave-length around 220 nm arose group. Thus a-linked glycosides gave arise to a positive band. methyl a-and B-glycosides of at the wave-length lower than 200 nm


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The anomeric configuration of sialic acid and its derivatives could be determined on the basis of the coupling pattern of C-l in the gated proton-decoupled or selective proton decoupled "C-NMR spectra; the a! anomer gave a doublet C-l signal while the fi gave a singlet. Recently much interest has b

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In D20 solution the lH-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 configuration: 6 [H(3e)l = 2.72 ? 0.05; 6 [H(3a)l = 2.32 2 0.08.