一种用于鸟嘌呤核苷C-6位修饰的简单方法。
A simple method for C-6 modification of guanine nucleosides.
作者信息
Lakshman Mahesh K, Frank Josh
机构信息
Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031-9198, USA.
出版信息
Org Biomol Chem. 2009 Jul 21;7(14):2933-40. doi: 10.1039/b905298d. Epub 2009 Jun 1.
Abstract
A facile method for the introduction of various substituents at the C-6 position of guanosine and 2'-deoxyguanosine is reported. In a simple, 1-step transformation, tert-butyldimethylsilyl protected guanosine and 2'-deoxyguanosine were converted to the O(6)-(benzotriazol-1-yl) derivatives via reaction with 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and 1,8-diazabicyclo[5.4.0]undec-7ene (DBU). The easily isolated, stable and storable, O(6)-(benzotriazol-1-yl) guanosine derivatives upon exposure to a range of nucleophiles, under appropriate conditions, led to the C-6 modified 2-amino purine nucleoside analogues in good yields.
摘要
报道了一种在鸟苷和2'-脱氧鸟苷的C-6位引入各种取代基的简便方法。在一个简单的一步转化中，叔丁基二甲基甲硅烷基保护的鸟苷和2'-脱氧鸟苷通过与1H-苯并三唑-1-基氧基三（二甲基氨基）鏻六氟磷酸盐（BOP）和1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）反应转化为O(6)-(苯并三唑-1-基)衍生物。在适当条件下，将易于分离、稳定且可储存的O(6)-(苯并三唑-1-基)鸟苷衍生物暴露于一系列亲核试剂中，可高产率地得到C-6修饰的2-氨基嘌呤核苷类似物。
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