Pyrrolo-dC and pyrrolo-C:: fluorescent analogs of cytidine and 2′-deoxycytidine for the study of oligonucleotides

被引:132
作者
Berry, DA
Jung, KY
Wise, DS
Sercel, AD
Pearson, WH
Mackie, H
Randolph, JB
Somers, RL
机构
[1] Berry & Associates Inc, Dexter, MI 48130 USA
[2] Glen Res Corp, Sterling, VA 20164 USA
关键词
D O I
10.1016/j.tetlet.2004.01.108
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyrrolo-dC (1a, 6-methyl-3-(2-deoxy-beta-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one) and its cyanoethyl phosphoramidite 2a were synthesized. The latter was incorporated into oligodeoxyribonucleotides by standard automated synthesis techniques, where pyrrolo-dC was found to serve as a fluorescent analog of deoxycytidine. The cyanoethylphosphoramidite (2b) of pyrrolo-C (2a, 6-methyl-3-(P-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one) was also synthesized and may find use for the site-specific incorporation of a fluorescent cytidine analog into oligoribonucleotides. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2457 / 2461
页数:5
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