Synthetic 6-O-Methylglucose-Containing Polysaccharides (sMGPs): Design and Synthesis

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• 作者：Malte Meppen ; Yonghui Wang ; Hwan-Sung Cheon ; Yoshito Kishi
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：March 16, 2007
• 年：2007
• 卷：72
• 期：6
• 页码：1941 - 1950
• 全文大小：240K
• 年卷期：v.72,no.6(March 16, 2007)
• ISSN：1520-6904

文摘

With the hope of mimicking the chemical and biological properties of natural 6-O-methyl-D-glucose-containing polysaccharides (MGPs), synthetic 6-O-methyl-D-glucose-containing polysaccharides (sMGPs)were designed and synthesized from mages/gifchars/alpha.gif" BORDER=0>-, mages/gifchars/beta2.gif" BORDER=0 ALIGN="middle">-, and mages/gifchars/gamma.gif" BORDER=0 >-cyclodextrins (CDs). The synthetic route proved to beflexible and general, to furnish a series of sMGPs ranging from 6-mer to 20-mer. A practical and scalablemethod was discovered selectively to cleave the CD derivatives and furnish the linear precursors to theglycosyl donors and acceptors. The Mukaiyama glycosidation was adopted to couple the glycosyl donorswith the glycosyl acceptors. Unlike in the 3-O-methyl-D-mannose-containing polysaccharide (sMMP)series, the amount of the Mukaiyama acid required in the sMGP series increased with an increase ofsubstrate size; that is, for large oligomers, more than one equivalent of the acid was required.