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未保护的卤代嘌呤碱基、核苷、核苷酸和核苷三磷酸与4-硼苯丙氨酸在水中的交叉偶联反应。(嘌呤-8-基)-和(嘌呤-6-基)苯丙氨酸的合成。

Cross-coupling reactions of unprotected halopurine bases, nucleosides, nucleotides and nucleoside triphosphates with 4-boronophenylalanine in water. Synthesis of (purin-8-yl)- and (purin-6-yl)phenylalanines.

作者信息

Capek Petr, Pohl Radek, Hocek Michal

机构信息

Centre for New Antivirals and Antineoplastics, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, CZ-16610, Prague 6, Czech Republic.

出版信息

Org Biomol Chem. 2006 Jun 7;4(11):2278-84. doi: 10.1039/b604010a. Epub 2006 May 4.

DOI:10.1039/b604010a
PMID:16729137
Abstract

An expeditious and highly efficient single-step methodology for the introduction of a phenylalanine moiety into position 8 and 6 of the purine scaffold was developed based on aqueous-phase Pd-catalysed Suzuki-Miyaura cross-coupling reactions of unprotected 4-boronophenylalanine with 8-bromo- or 6-chloropurines. The scope of the methodology was demonstrated by syntheses of unprotected (adenin-8-yl)phenylalanine base, nucleosides, nucleotides and nucleoside triphosphates as well as (purin-6-yl)phenylalanine base and nucleosides. All these products were obtained in high yields and in optically pure form.

摘要

基于未保护的4-硼苯丙氨酸与8-溴嘌呤或6-氯嘌呤在水相钯催化的铃木-宫浦交叉偶联反应，开发了一种快速高效的单步方法，用于将苯丙氨酸部分引入嘌呤骨架的8位和6位。通过合成未保护的（腺嘌呤-8-基）苯丙氨酸碱基、核苷、核苷酸和核苷三磷酸以及（嘌呤-6-基）苯丙氨酸碱基和核苷，证明了该方法的适用范围。所有这些产物均以高收率和光学纯形式获得。

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