Synthesis of modified tuftsins containing monosaccharides or monosaccharide derivatives
1987; Wiley; Volume: 29; Issue: 2 Linguagem: Inglês
10.1111/j.1399-3011.1987.tb02252.x
ISSN0367-8377
AutoresRaniero Rocchi, Laura Biondi, Fernando Filira, Marina Gobbo, Shlomo Dagan, Mati Fridkin,
Tópico(s)Diet, Metabolism, and Disease
ResumoSynthesis of some modified tuftsins is described in which a monosaccharide or a monosaccharide derivative was incorporated in the molecule. Acylation of H‐Thr‐Lys(Z)‐Pro‐Arg(NO 2 )‐OBzl with D(+)‐gluco‐1,5‐lactone followed by catalytic hydrogenation gave N α‐gluconyl‐tuftsin. Glycosylation of the carboxyl function of the C ‐terminal arginine has been achieved by reacting, through the mixed anhydride procedure, Boc‐Thr‐Lys(Z)‐Pro‐OH with 2‐deoxy‐2‐( N G ‐nitroargininamido)‐D‐glucopyranose followed by catalytic hydrogenation and trifluoroacetic acid treatment. O ‐Glucosyl‐tuftsin has been prepared by reacting o ‐nitrophenyl N ‐benzyloxycarbonyl‐ O ‐[(α + β)2,3,4,6‐tetra‐ O ‐benzyl‐D‐grucopyranosyl]‐threoninate with H‐Lys(Z)‐Pro‐Arg(NO 2 )‐OBzl in the presence of 1‐hydroxybenzotriazole. Flash chromatography on silica gel allowed a partial separation of the diastereoisomers, one of which has been isolated in a reasonable yield. The single diasteroisomer and the α + β anomeric mixture were separately deblocked by catalytic hydrogenation and purified by RP‐HPLC.
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