SYNTHESIS OF O-[2-ACETAMIDO-2-DEOXY-6-O-STEAROYL- AND -6-O-(2-TETRADECYLHEXADECANOYL)-BETA-D-GLUCOPYRANOSYL]-(1-]4)N-ACETYLNORMURAMOYL-L-ALPHA-AMINOBUTANOYL-D-ISOGLUTAMINE, LIPOPHILIC DISACCHARIDE ANALOGS OF MDP

被引：4

作者：

LEDVINA, M ^{[1
]}

JEZEK, J ^{[1
]}

SAMAN, D ^{[1
]}

VAISAR, T ^{[1
]}

HRIBALOVA, V ^{[1
]}

机构：

[1] NATL INST PUBL HLTH, 10042 PRAGUE 10, CZECH REPUBLIC

来源：

CARBOHYDRATE RESEARCH | 1994年 / 251卷

关键词：

D O I：

10.1016/0008-6215(94)84291-4

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Silver triflate-promoted condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glycopyranosyl bromide (1) with benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methoxycarbonyl)methyl-alpha-D-glycopyranoside (4) afforded the key compound, benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methoxycarbonyl)methyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-alpha-D-glucopyranoside(5),which after deprotection was transformed into acid 10. Condensation of 10 with the benzyl ester of L-alpha-aminobutanoyl-D-isoglutamine and deisopropylidenation of the product 11 afforded the benzyl ester of N-{2-O[benzyl 2-acetamido-4-O-(2-acetamido-3-O-benzyloxymethyl-2-deoxy-beta-D-glycopyranosyl)-6-O-benzyl-2,3-dideoxy-alpha -D-glucopyranosid-3-yl]glycoloyl}-L-alpha- aminobutanoyl-D-isoglutamine (12). Partial O-acylation of 12 and hydrogenolysis of protecting groups gave the 6-O-stearoyl- and 6-O-(2-tetradecylhexadecanoyl)-disaccharide-dipeptides 17 and 18, respectively. Pyrogenicity and adjuvant activity in cell-mediated immunity are reported.

引用

页码：269 / 284

页数：16

共 16 条

[1]

CASTRO B, 1975, TETRAHEDRON LETT, P1219

[2] SYNTHESIS OF ANALOGS OF BACTERIAL CELL WALL GLYCOPEPTIDES [J].