一条通往3'-氨基-3'-脱氧腺苷衍生物和嘌呤霉素类似物的实用路线。

A practical route to 3'-amino-3'-deoxyadenosine derivatives and puromycin analogues.

作者信息

Nguyen-Trung Nhat Quang, Botta Oliver, Terenzi Silvia, Strazewski Peter

机构信息

Institute of Organic Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland.

出版信息

J Org Chem. 2003 Mar 7;68(5):2038-41. doi: 10.1021/jo026627c.

DOI:10.1021/jo026627c

PMID:12608833

Abstract

3'-aminoacylamino-3'-deoxyadenosines, analogues of the antibiotic puromycin, have been synthesized from adenosine. They key 3'-azido derivative 10 was obtained through a 3'-oxidation/reduction/substitution procedure. A modified purification protocol on a larger scale was developed for the oxidation step using the Garegg reagent. The coupling reaction between an Fmoc-l-amino acid and the fully protected form of 3'-amino-3'-deoxyadenosine 11 furnished the aminoacylated compounds 12 in high yields. The puromycin analogues were obtained in 10 steps and up to 23% (14c) overall yield.

摘要

3'-氨酰基氨基-3'-脱氧腺苷，即抗生素嘌呤霉素的类似物，已由腺苷合成。关键的3'-叠氮基衍生物10是通过3'-氧化/还原/取代过程获得的。使用加雷格试剂为氧化步骤开发了一种更大规模的改良纯化方案。Fmoc-L-氨基酸与3'-氨基-3'-脱氧腺苷11的完全保护形式之间的偶联反应以高产率提供了氨酰化化合物12。嘌呤霉素类似物通过10步反应获得，总产率高达23%（14c）。