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2'-脱氧-2'-C-α-甲基胞苷和2'-脱氧-2'-C-α-羟甲基胞苷的亚磷酰胺衍生物的合成：用于对RNA的2'-羟基进行化学剖析的类似物

Synthesis of the phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-methylcytidine and 2'-deoxy-2'-C-alpha-hydroxymethylcytidine: analogues for chemical dissection of RNA's 2'-hydroxyl group.

作者信息

Li Nan-Sheng, Piccirilli Joseph A

机构信息

Department of Biochemistry and Molecular Biology, University of Chicago, 5841 South Maryland Avenue, MC 1028, Chicago, Illinois 60637, USA.

出版信息

J Org Chem. 2004 Jul 9;69(14):4751-9. doi: 10.1021/jo0495337.

DOI:10.1021/jo0495337
PMID:15230598
Abstract

Oligonucleotides containing 2'-C-alpha-methyl and 2'-C-alpha-hydroxymethyl modifications enable strategies for delineation of the distinctive role fulfilled by the 2'-hydroxyl group in RNA structure and function. Synthetic routes to the phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-methylcytidine (14%, 15 steps) and 2'-deoxy-2'-C-alpha-hydroxymethylcytidine (19%, 10 steps) from methyl 3,5-di-O-(4-chlorobenzyl)-alpha-d-ribofuranoside are developed.

摘要

含有2'-C-α-甲基和2'-C-α-羟甲基修饰的寡核苷酸，为阐明2'-羟基在RNA结构和功能中所起的独特作用提供了策略。已开发出从3,5-二-O-(4-氯苄基)-α-D-呋喃核糖苷甲基合成2'-脱氧-2'-C-α-甲基胞苷（产率14%，15步）和2'-脱氧-2'-C-α-羟甲基胞苷（产率19%，10步）亚磷酰胺衍生物的路线。

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