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氢键介导的糖苷配基递送:直链和支链α-葡聚糖的合成。

Hydrogen bond mediated aglycone delivery: synthesis of linear and branched α-glucans.

机构信息

Department of Chemistry and Biochemistry, University of Missouri, St. Louis, One University Boulevard, St. Louis, MO 63121 (USA) http://www.umsl.edu/chemistry/faculty/demchenko.htm.

出版信息

Angew Chem Int Ed Engl. 2014 Sep 22;53(39):10453-6. doi: 10.1002/anie.201405084. Epub 2014 Aug 12.

DOI:10.1002/anie.201405084
PMID:25115776
Abstract

A Hydrogen bond mediated aglycone delivery (HAD) method was applied to the synthesis of α-glucans, which are abundant in nature, but as targets represent a notable challenge to chemists. The synthesis of linear oligosaccharide sequences was accomplished in complete stereoselectivity in all glycosylations. The efficacy of HAD may diminish with the increased bulk of the glycosyl acceptor, and may be an important factor for the syntheses of oligomers beyond pentasaccharides. The synthesis of a branched structure proved more challenging, particularly with bulky trisaccharide acceptors.

摘要

氢键介导的糖苷配基传递 (HAD) 方法被应用于α-葡聚糖的合成,α-葡聚糖在自然界中含量丰富,但作为化学合成的目标,它们具有显著的挑战性。在所有糖苷化反应中,线性寡糖序列的合成都具有完全的立体选择性。HAD 的功效可能随糖苷受体的体积增大而降低,这可能是合成五糖以上寡聚物的一个重要因素。分支结构的合成更具挑战性,特别是使用较大的三糖受体。

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