β-D-氨基葡萄糖-（1→3）-α-L-鼠李糖-（1→2）-[β-L-木糖-（1→4）]-α-L-鼠李糖-（1→3）-α-L-鼠李糖的合成，这是由青枯雷尔氏菌ICMP 7942产生的O抗原的重复单元。

Synthesis of beta-D-GlcpNAc-(1-->3)-alpha-L-Rhap-(1-->2)-[beta-L-Xylp-(1-->4)]-alpha-L-Rhap-(1-->3)-alpha-L-Rhap, the repeating unit of the O-antigen produced by Pseudomonas solanacearum ICMP 7942.

作者信息

Zhang Jianjun, Kong Fanzuo

机构信息

Research Center for Eco-Environmental Sciences, Academia Sinica, Chinese Academy of Sciences, PO Box 2871, Beijing 100085, PR China.

出版信息

Carbohydr Res. 2003 Jan 2;338(1):19-27. doi: 10.1016/s0008-6215(02)00358-0.

DOI:10.1016/s0008-6215(02)00358-0

PMID:12504377

Abstract

An efficient synthesis of beta-D-GlcpNAc-(1-->3)-alpha-L-Rhap-(1-->2)-[beta-L-Xylp-(1-->4)]-alpha-L-Rhap-(1-->3)-alpha-L-Rhap, the repeating unit of the O-antigen produced by Pseudomonas solanacearum ICMP 7942 and its isomer beta-D-GlcpNAc-(1-->3)-alpha-L-Rhap-(1-->4)-[beta-L-Xylp-(1-->2)]-alpha-L-Rhap-(1-->3)-alpha-L-Rhap was achieved via sequential assembly of the building blocks, allyl 2,3-O-isopropylidene-alpha-L-rhamnopyranoside (2), allyl 3,4-O-isopropylidene-alpha-L-rhamnopyranoside (3), allyl 2,4-di-O-benzoyl-alpha-L-rhamnopyranoside (6), 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate (7), and 2,3,4-tri-O-benzoyl-beta-L-xylopyranosyl trichloroacetimidate (12). The process was carried out in a regio- and stereoselective manner using glycosyl trichloroacetimidates as donors and unprotected or partially protected rhamnopyranosides as acceptors in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf).

摘要

高效合成了青枯假单胞菌ICMP 7942产生的O抗原重复单元β-D-氨基葡萄糖-(1→3)-α-L-鼠李糖-(1→2)-[β-L-木糖-(1→4)]-α-L-鼠李糖-(1→3)-α-L-鼠李糖及其异构体β-D-氨基葡萄糖-(1→3)-α-L-鼠李糖-(1→4)-[β-L-木糖-(1→2)]-α-L-鼠李糖-(1→3)-α-L-鼠李糖，该合成过程通过依次组装烯丙基2,3-O-异亚丙基-α-L-鼠李吡喃糖苷（2）、烯丙基3,4-O-异亚丙基-α-L-鼠李吡喃糖苷（3）、烯丙基2,4-二-O-苯甲酰基-α-L-鼠李吡喃糖苷（6）、3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚氨基-β-D-吡喃葡萄糖基三氯乙酰亚胺酯（7）和2,3,4-三-O-苯甲酰基-β-L-木糖基三氯乙酰亚胺酯（12）来实现。该过程在催化量的三甲基甲硅烷基三氟甲磺酸酯（TMSOTf）存在下，以区域和立体选择性的方式进行，使用三氯乙酰亚胺酯糖基作为供体，未保护或部分保护的鼠李吡喃糖苷作为受体。