[Lengthening of the peptide chain at the C-terminal end of a glycosylamino acid].
An O-glycodipeptide was synthesized by lengthening the peptide chain on the C-terminal side of a glycosylamino acid unit. N-(Benzyloxycarbonyl)-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-L-threonine o-nitrophenyl ester and pentachlorophenyl ester were condensed with glycine benzyl ester to give both the same glycodipeptide, [N-(benzyloxycarbonyl)-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-L-threonyl]glycine benzyl ester (9). The two anomers, N-(benzyloxycarbonyl)-3-O-(2,3,4,6-tetra-O-acetyl-alpha- and beta-D-glucopyranosyl)-L-threonine pentachlorophenyl ester were also prepared. 1H-N.m.r. studies ascertained the structure and anomeric configuration expected.
D004151:Dipeptides; D005947:Glucose; D006023:Glycoproteins / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D004151:Dipeptides; D006023:Glycoproteins; D005947:Glucose
Allongement de la chaîne peptidique du côté C-terminal d'un glycosylaminoacide