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Titolo:
SYNTHESIS AND STRUCTURAL STUDIES OF BRANCHED 2-LINKED TRISACCHARIDES RELATED TO BLOOD-GROUP DETERMINANTS
Autore:
DUUS JO; NIFANTEV N; SHASHKOV AS; KHATUNTSEVA EA; BOCK K;
Indirizzi:
CARLSBERG LAB,DEPT CHEM,GAMLE CARLSBERG VEJ 10 DK-2500 COPENHAGEN DENMARK CARLSBERG LAB,DEPT CHEM DK-2500 COPENHAGEN DENMARK RUSSIAN ACAD SCI,ND ZELINSKY INST ORGAN CHEM MOSCOW 117913 RUSSIA
Titolo Testata:
Carbohydrate research
, volume: 288, anno: 1996,
pagine: 25 - 44
SICI:
0008-6215(1996)288:<25:SASSOB>2.0.ZU;2-8
Fonte:
ISI
Lingua:
ENG
Soggetto:
ALPHA-L-RHAMNOPYRANOSIDES; METHYL BETA-GLYCOSIDES; C-13 NMR-SPECTRA; CONFORMATIONAL-ANALYSIS; D-GALACTOPYRANOSIDES; GALACTOSE RESIDUE; 2,3,4-TRI-O-BENZOYL-ALPHA-L-FUCOPYRANOSYL BROMIDE; OLIGOSACCHARIDES; POLYSACCHARIDES; DERIVATIVES;
Keywords:
OLIGOSACCHARIDES; SYNTHESIS; NMR SPECTROSCOPY; CONFORMATIONS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
35
Recensione:
Indirizzi per estratti:
Citazione:
J.O. Duus et al., "SYNTHESIS AND STRUCTURAL STUDIES OF BRANCHED 2-LINKED TRISACCHARIDES RELATED TO BLOOD-GROUP DETERMINANTS", Carbohydrate research, 288, 1996, pp. 25-44

Abstract

A series of trisaccharide glycosides, Fuc-(1 --> 2)-beta-Gal-(1 --> 3)-beta-X-OMe (X = GlcNAc, Glc, 2-deoxy-Glc) related to the blood groupdeterminant Led have been synthesised both as their alpha- and beta-Fuc anomers together with the component disaccharide starting compounds. The conformational properties of the six trisaccharides together with their parent disaccharides have been investigated by NMR spectroscopy (proton and carbon chemical shifts and proton NOEs) in combination with computer modeling using the Monte Carlo approach and the HSEA force field using the GEGOP programme. The interaction between the terminal fucose unit and the reducing unit was probed by substitution of the bulky NAc group with hydroxyl and deoxy substituents, respectively. Compounds with severe steric interactions were identified by the non-additivity of their carbon chemical shifts. This was subsequently confirmed by the detailed conformational assessment by NOE spectroscopy and computer modeling. The most severe contacts arose in the alpha-L-Fuc derivatives, whereas the beta-linked L-Fuc derivatives only in one case exhibit severe steric interaction as probed by the NMR parameters. (C)1996 Elsevier Science Ltd.

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Documento generato il 07/08/20 alle ore 00:14:45