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Titolo:
Synthesis and characterization of an anomeric sulfur analogue of CMP-sialic acid
Autore:
Cohen, SB; Halcomb, RL;
Indirizzi:
Univ Colorado, Dept Chem & Biochem, Boulder, CO 80309 USA Univ Colorado Boulder CO USA 80309 Chem & Biochem, Boulder, CO 80309 USA
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 19, volume: 65, anno: 2000,
pagine: 6145 - 6152
SICI:
0022-3263(20000922)65:19<6145:SACOAA>2.0.ZU;2-D
Fonte:
ISI
Lingua:
ENG
Soggetto:
ENZYMATIC-SYNTHESIS; RAT-LIVER; OLIGOSACCHARIDES; DIMETHYLDIOXIRANE; SIALYLATION; ACTIVATION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
24
Recensione:
Indirizzi per estratti:
Indirizzo: Halcomb, RL Univ Colorado, Dept Chem & Biochem, Campus Box 215, Boulder, CO 80309 USA Univ Colorado Campus Box 215 Boulder CO USA 80309 CO 80309 USA
Citazione:
S.B. Cohen e R.L. Halcomb, "Synthesis and characterization of an anomeric sulfur analogue of CMP-sialic acid", J ORG CHEM, 65(19), 2000, pp. 6145-6152

Abstract

alpha-2,3-Sialyltransferase catalyzes the transfer of sialic acid from CMP-sialic acid (1) to a lactose acceptor. An analogue of 1 was synthesized inwhich the anomeric oxygen atom was replaced with a sulfur atom (1S). The key step in the synthesis of 1S was a tetrazole-promoted coupling of a cytidine-5'-phosphoramidite with a glycosyl thiol of a protected sialic acid. Compounds 1 and 1S were characterized for their activity in a sialyl transferassay. The rate of solvolysis in aqueous buffer of analogue 1S was 50-foldslower than that of 1. Analogue 1S was found to be substrate for alpha-2,3-sialyltransferase. The K-m of 1S was just 3-fold higher than that of 1, while the k(cat) of 1S was 2 orders of magnitude lower compared to 1.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 11/07/20 alle ore 20:37:52