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001-es BibID:	BIBFORM019664
Első szerző:	Czifrák Katalin (vegyész)
Cím:	Synthesis of some derivatives of C-(1-deoxy-1-N-substituted-d-glucopyranosyl)formic acid (d-gluco-hept-2-ulopyranosonic acid) as potential inhibitors of glycogen phosphorylase / Katalin Czifrák, László Kovács, Katalin E. Kövér, László Somsák
Dátum:	2005
ISSN:	0008-6215
Megjegyzések:	Per-O-benzoylated derivatives (amide, methyl ester and glycinamide) of C-(1-azido-1-deoxy-alpha-D-glucopyranosyl)formic acid obtained by azide substitution in the corresponding C-(1-bromo-1-deoxy-beta-D-glucopyranosyl)formic acid derivatives were debenzoylated by the Zemple?n-protocol. Per-O-benzoylated C-(1-azido-1-deoxy-alpha-D-glucopyranosyl)formamide was dehydrated by oxalyl chloride?DMF to give the corresponding nitrile, while from its reduction mixture obtained by Raney-nickel or sodium hydrogentelluride C-(1-amino-1-deoxy-beta-D-glucopyranosyl)formamide could be isolated. Acetylation of this amino-amide by Ac2O/Py and subsequent debenzoylation gave C-(1-acetamido-1-deoxy-beta-D-glucopyranosyl)formamide. Applying the same conditions to the crude reduction mixture allowed the alpha-anomer to be isolated as a minor component. An alternative pathway to produce the above beta-anomer appeared in the reaction of C-(1-bromo-1-deoxy-beta-D-glucopyranosyl)formamide with CH3CN in the presence of Ag2CO3 to yield 1-acetamido-2,3,4,6,-tetra-O-benzoyl-1-deoxy-beta-D-glucopyranosyl cyanide, which was hydrated, in the presence of TiCl4, to the formamide. Some of the new compounds were shown to be weak inhibitors of muscle glycogen phosphorylase b.
Tárgyszavak:	Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban Glycosyl azides Glycosyl amides Hept-2-ulopyranosonic acid derivatives Glycogen phosphorylase inhibitors
Megjelenés:	Carbohydrate Research. - 340 : 14 (2005), p. 2328-2334. -
További szerzők:	Kovács László Kövér Katalin, E. (1956-2023) (vegyész) Somsák László (1954-) (vegyész)
Pályázati támogatás:	T46081 OTKA T43550 OTKA
Internet cím:	Szerző által megadott URL DOI Intézményi repozitóriumban (DEA) tárolt változat
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