A peptide-based catalyst approach to regioselective functionalization of carbohydrates
A peptide-based catalyst approach to regioselective functionalization of carbohydrates
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DOI：
10.1016/j.tet.2003.05.002
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发表时间：
2003-11-03
期刊：
影响因子：
2.1
通讯作者：
Miller, SJ
中科院分区：
文献类型：
--
作者：
Griswold, KS;Miller, SJ
两个小的肽库（150个成员和36个成员）已进行筛选实验，以评估其潜在的区域选择性（即位点选择性）酰化的碳水化合物单体。两种底物，一种二醇衍生自N-乙酰葡糖胺和一种四醇衍生自葡萄糖，已作为测试案例。在每种情况下，催化酰化的固有区域选择性被定义为来自N-甲基咪唑（NMI）用作催化剂的反应。对于这两种底物，发现肽干扰了用NMI观察到的固有选择性。从库中，对提供与NMI的最大偏差的催化剂进行优化研究。这项工作奠定了基础的研究扩大肽库和发展的结构选择性关系，以获得催化剂，可以选择性地衍生化立体化学复杂的多元醇中的独特位点。(C)2003 Elsevier Ltd.保留所有权利。
Two small peptide libraries (150 members and 36 members) have been subjected to screening experiments to evaluate their potential for regioselective (i.e. site-selective) acylation of carbohydrate monomers. Two substrates, one diol derived from N-acetyl glucosamine and one tetraol derived from glucose, have served as the test cases. In each case, the inherent regioselection of catalyzed acylation was defined as that derived from the reaction where N-methylimidazole (NMI) is used as the catalyst. With both substrates, peptides were found to perturb the inherent selectivities from those observed with NMI. From the libraries, the catalysts that provide the largest deviation from NMI were subjected to optimization studies. The work sets the groundwork for studies of expanded peptide libraries and development of structure-selectivity relationships to obtain catalysts that can selectively derivatize the unique sites in stereochemically complex polyols. (C) 2003 Elsevier Ltd. All rights reserved.