Synthesis of an alpha-linked dimer of the trisaccharide repeating unit of the exopolysaccharide produced by Pediococcus damnosus 2.6

doi:10.1016/j.carres.2004.07.026

CORC > 生态环境研究中心 > 中国科学院生态环境研究中心 > 中国科学院环境生物技术重点实验室

	Synthesis of an alpha-linked dimer of the trisaccharide repeating unit of the exopolysaccharide produced by Pediococcus damnosus 2.6
	Li, AX; Kong, FZ
刊名	CARBOHYDRATE RESEARCH
	2004
卷号	339 期号:15 页码:2499-2506
关键词	Glucan Trichloroacetimidates Synthesis
DOI	10.1016/j.carres.2004.07.026
英文摘要	A hexasaccharide, beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->2)]-alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->2)]-D-Glcp, the alpha-linked dimer of the trisaccharide repeating unit of the exopolysaccharide produced by Pediococcus damnosus 2.6, was synthesized as its methyl glycoside. Condensation of fully benzoylated alpha-D-glucopyranosyl trichloroacetimidate (1) with isopropyl 4,6-O-benzylid,ene-1-thio-beta-D-glucopyranoside (2) selectively furnished (1-->3)-linked disaccharide 3, and subsequent 2-O-acetylation, desulfation, and trichloroacetimidate formation afforded the disaccharide donor 6. Meanwhile, selective 3-O-coupling of methyl 4,6-O-benzylidene-alpha-D-glucopyranoside (8) with 3-O-allyl-2,4,6-tri-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate (7), followed by coupling with 1 gave the trisaccharide 10. Removal of the benzylidene group of 10, benzoylation, and deallylation produced the trisaccharide acceptor 12. Condensation of 12 with 6 yielded a pentasaccharide mixture 13 with (3 and a isomers in a ratio of 2:1. Removal of the benzylidene group of 13, followed by benzoylation gave the pentasaccharide mixture 14. Selective 2"'-deacetylation of the isolated beta-linked 14 beta with MeCOCl/MeOH/CH2Cl2 did not give the expected pentasaccharide acceptor, and serious decomposition occurred, indicating a large steric hindrance at C-2"'. Alternatively, 2,3-di-O-glycosylation of allyl 4,6-O-benzylidene-beta-D-glucopyranoside (21) with 1 gave 22, then deallylation and trichloroacetimidate formation afforded the trisaccharide donor 24. Condensation of 12 with 24 furnished only the alpha-linked hexasaccharide 25, and its deprotection gave the free hexaoside 27. (C) 2004 Elsevier Ltd. All rights reserved.
WOS研究方向	Biochemistry & Molecular Biology ; Chemistry
WOS记录号	WOS:000224716400003
内容类型	期刊论文
源URL	[http://ir.rcees.ac.cn/handle/311016/23599]
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	Li, AX,Kong, FZ. Synthesis of an alpha-linked dimer of the trisaccharide repeating unit of the exopolysaccharide produced by Pediococcus damnosus 2.6[J]. CARBOHYDRATE RESEARCH,2004,339(15):2499-2506.
APA	Li, AX,&Kong, FZ.(2004).Synthesis of an alpha-linked dimer of the trisaccharide repeating unit of the exopolysaccharide produced by Pediococcus damnosus 2.6.CARBOHYDRATE RESEARCH,339(15),2499-2506.
MLA	Li, AX,et al."Synthesis of an alpha-linked dimer of the trisaccharide repeating unit of the exopolysaccharide produced by Pediococcus damnosus 2.6".CARBOHYDRATE RESEARCH 339.15(2004):2499-2506.