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Chemical modification of the carbohydrate moiety in n acetylmuramoyl l alanyl d iso glutamine and the immuno adjuvant activity



Chemical modification of the carbohydrate moiety in n acetylmuramoyl l alanyl d iso glutamine and the immuno adjuvant activity



Carbohydrate Research 92(1): 75-84



Five carbohydrate analogs of N-acetylmuramoyl-L-analyl-D-isoglutamine were synthesized from benzyl 2-acetamido-2-deoxy-3-O-[D-1-(methoxycarbonyl)-1-ethyl]-.alpha.-D-glucopyranoside (1) and the corresponding 6-O-benzoyl derivative (2). Chlorination of 1 and 2 with triphenylphosphosphine in CCl4 gave the 4,6-dichloro compound 3 and the 6-O-benzoyl-4-chloro compound (4), which were treated with tributylin hydride, to yield benzyl 2-acetamido-2,4,6-trideoxy-3-O-[D-1-(methoxycarbonyl)ethyl]-.alpha.-D-xylo-hexopyranoside (6) and benzyl 2-acetamido-6-O-benzoyl-2,4-dideoxy-3- O-[D-1-(methoxycarbonyl)ethyl]-.alpha.-D-xylo-hexopyranoside (7), respectively. Methanesulfonylation of [benzyl-2-acetamido-2,4-dideoxy-3-O-[D-1-(methoxycarbonyl)ethyl]-.alpha.-D-xylo-hexopyranoside] 8, derived from 7 by debenzoylation, gave the 6-methanesulfonate, which underwent displacement with azide ion to afford benzyl 2-acetamido-6-azido-2,4,6-trideoxy-3-O-[D-1-(methoxycarbonyl)ethyl]-.alpha.-D-xylo-hexopyranoside (10). Hydrolysis of the methyl ester group in compounds 3, (debenzoylated 4), 6, 8 and 10 gave the corresponding free acids, which were coupled with L-alanyl-D-isoglutamine benzyl ester, to yield the dipeptide derivatives in excellent yields. Hydrogenation of the dipeptide derivatives obtained gave the 5 carbohydrate analogs of N-acetylmuramoyl-L-alanyl-D-isoglutamine, respectively, in good yields. The immunoadjuvant activity of the N-acetylmuramoyl-dipeptide analogs was examined in guinea pigs.

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