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001-es BibID:	bibEBI00008373
Első szerző:	Gyóllai Viktor
Cím:	Preparation of acetylated 1-fluoroglycopyranosyl cyanides / Viktor Gyóllai, László Somsák, Zoltán Györgydeák
Dátum:	1998
ISSN:	0040-4020
Megjegyzések:	Reactions of acetylated 1-bromo-1-deoxy-glycopyranosyl cyanides of β-d-galacto (2) and α-d-arabino (12) configurations with silver fluoride in acetonitrile at room temperature gave the corresponding 1-deoxy-1-fluoroglycopyranosyl cyanides (5 and 13, respectively) with inversion of the anomeric centre. Under similar conditions the β-d-gluco (1) and β-d-xylo (3) compounds resulted in the corresponding inverted 1-fluoroglycosyl cyanides (4 and 6, respectively) together with significant amounts of 1-cyano-2-hydroxy-glycals (9 and 10, respectively). Silver tetrafluoroborate in toluene at room temperature converted 2 and 3 into the 1-fluoroglycosyl cyanides (7 and 8, respectively) of retained anomeric configuration. 1-Chloro-1-deoxy-α-d-galactopyranosyl cyanide (11) also gave 7 with silver fluoride in acetonitrile at reflux temperature. Conformational equilibria of the 1-deoxy-1-fluoro-pentopyranosyl cyanides 6, 8, and 13 reflect counteraction of the anomeric effects exerted by the fluorine and the cyano group. 1-Deoxy-1-fluoro-α-d-galactopyranosyl cyanide proved to be a weak competitive inhibitor if E. coli β-d-galactosidase (Ki = 2 mM).
Tárgyszavak:	Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény hazai lapban carbohydrates cyano compounds fluorine compounds enzyme inhibitors
Megjelenés:	Tetrahedron. - 54 :43 (1998), p. 13267-13276. -
További szerzők:	Somsák László (1954-) (vegyész) Györgydeák Zoltán (1942-2005) (vegyész)
Internet cím:	Szerző által megadott URL DOI Intézményi repozitóriumban (DEA) tárolt változat
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