一种使万古霉素“氯化物”多样化的逐步脱氯/交叉偶联策略。
A stepwise dechlorination/cross-coupling strategy to diversify the vancomycin 'in-chloride'.
作者信息
Wadzinski Tyler J, Gea Katherine D, Miller Scott J
机构信息
Department of Chemistry, Yale University, PO Box 208107, New Haven, CT 06520-8107, United States.
Department of Chemistry, Yale University, PO Box 208107, New Haven, CT 06520-8107, United States.
出版信息
Bioorg Med Chem Lett. 2016 Feb 1;26(3):1025-1028. doi: 10.1016/j.bmcl.2015.12.027. Epub 2015 Dec 11.
Abstract
In an effort to rapidly access vancomycin analogues bearing diverse functionality at the 6c-Cl (the 'in-chloride') position, a two-step dechlorination/cross-coupling protocol was developed. Conditions for efficient cross-coupling of the relatively unreactive 6c-Cl group were found that ensure high conversion with minimal product decomposition. A set of 2c-dechloro-6c-functionalized vancomycin derivatives was prepared, and antibiotic activities of the compounds were evaluated against a panel of vancomycin-resistant and vancomycin-susceptible strains. Results from biological testing further underscore the steric sensitivity of vancomycin's binding pocket.
摘要
为了快速获得在6c-Cl（“内氯化物”）位置带有不同官能团的万古霉素类似物，开发了一种两步脱氯/交叉偶联方案。发现了相对不活泼的6c-Cl基团有效交叉偶联的条件，可确保高转化率且产物分解最少。制备了一组2c-脱氯-6c-官能化的万古霉素衍生物，并评估了这些化合物对一组耐万古霉素和对万古霉素敏感菌株的抗菌活性。生物学测试结果进一步强调了万古霉素结合口袋的空间敏感性。
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