Synthesis of two isomeric pentasaccharides, the possible repeating unit of the beta-glucan from the micro fungus Epicoccum nigrum Ehrenb. ex Schlecht

doi:10.1016/S0008-6215(02)00317-8

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	Synthesis of two isomeric pentasaccharides, the possible repeating unit of the beta-glucan from the micro fungus Epicoccum nigrum Ehrenb. ex Schlecht
	Zeng, Y; Zhang, WH; Ning, J; Kong, FZ
刊名	CARBOHYDRATE RESEARCH
	2002
卷号	337 期号:24 页码:2383-2391
关键词	Glucose Oligosaccharides Trichloroacetimidates Regio- And Stereoselective Synthesis
DOI	10.1016/S0008-6215(02)00317-8
英文摘要	Two isomeric pentasaccharides, beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 6)]-beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 6)]-beta-D-Glcp (I) and beta-D-Glcp-(1 --> 6)-beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 3)-beta-D-Glcp-(1 --> 6)]-beta-D-Glcp (II), the possible repeating unit of the beta-glucan from the micro fungus Epicoccum nigrum Ehrenb. ex Schlecht, were synthesized as their 4-methoxyphenyl glycosides in a regio- and stereoselective manner. The pentasaccharide I was obtained from 3-O-selective glycosylation of 4-methoxyphenyl 4,6-O-benzylidene-beta-D-glucopyranoside (12) with 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 --> 3)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 --> 6)]-2,4-di-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (6) followed by acetylation, debenzylidenation, and 6-O-selective glucosylation with 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl trichloroacetimidate (1), and then by deprotection. The pentasaccharide II was obtained from 3-O-selective coupling of 12 with 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 --> 6)-2,4-di-O-acetyl-3-O-allyl-alpha-D-glucopyranosyl trichloroacetimidate (10) followed by acetylation, debenzylidenation, and 6-O-selective glycosylation with 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (II), and finally by deprotection. (C) 2002 Elsevier Science Ltd. All rights reserved.
WOS研究方向	Biochemistry & Molecular Biology ; Chemistry
WOS记录号	WOS:000179688900002
内容类型	期刊论文
源URL	[http://ir.rcees.ac.cn/handle/311016/23975]
专题	生态环境研究中心_中国科学院环境生物技术重点实验室
推荐引用方式 GB/T 7714	Zeng, Y,Zhang, WH,Ning, J,et al. Synthesis of two isomeric pentasaccharides, the possible repeating unit of the beta-glucan from the micro fungus Epicoccum nigrum Ehrenb. ex Schlecht[J]. CARBOHYDRATE RESEARCH,2002,337(24):2383-2391.
APA	Zeng, Y,Zhang, WH,Ning, J,&Kong, FZ.(2002).Synthesis of two isomeric pentasaccharides, the possible repeating unit of the beta-glucan from the micro fungus Epicoccum nigrum Ehrenb. ex Schlecht.CARBOHYDRATE RESEARCH,337(24),2383-2391.
MLA	Zeng, Y,et al."Synthesis of two isomeric pentasaccharides, the possible repeating unit of the beta-glucan from the micro fungus Epicoccum nigrum Ehrenb. ex Schlecht".CARBOHYDRATE RESEARCH 337.24(2002):2383-2391.