A facile two-step synthesis of 8-arylated guanosine mono- and triphosphates (8-aryl GXPs)

被引:46
作者
Collier, Alice [1 ]
Wagner, Gerd [1 ]
机构
[1] Univ E Anglia, Sch Chem Sci & Pharm, Ctr Carbohydrate Chem, Norwich NR4 7TJ, Norfolk, England
关键词
D O I
10.1039/b614477b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report a simple and high-yielding two-step procedure for the preparation of 8-arylated guanosine mono- and triphosphates (8-aryl GXPs). The key step of our synthesis is the Suzuki - Miyaura coupling of unprotected 8-bromo GMP and 8-bromo GTP with various arylboronic acids in aqueous solution. The 8-bromoguanosine 5'-phosphates required as cross-coupling substrates were prepared from 8-bromoguanosine via an optimised Yoshikawa procedure.
引用
收藏
页码:4526 / 4532
页数:7
相关论文
共 35 条
[1]   Palladium-assisted routes to nucleosides [J].
Agrofoglio, LA ;
Gillaizeau, I ;
Saito, Y .
CHEMICAL REVIEWS, 2003, 103 (05) :1875-1916
[2]  
Amann N, 2002, SYNLETT, P687
[3]   General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].
Anderson, KW ;
Buchwald, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177
[4]   BIOSYNTHESIS OF POLYNUCLEOTIDES .3. SELECTIVE PHOSPHORYLATION OF ADENOSINE [J].
BARKER, GR ;
FOLL, GE .
JOURNAL OF THE CHEMICAL SOCIETY, 1957, (AUG) :3798-3800
[5]   Syntheses of nucleoside triphosphates [J].
Burgess, K ;
Cook, D .
CHEMICAL REVIEWS, 2000, 100 (06) :2047-2059
[6]   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 [J].
Capek, Petr ;
Pohl, Radek ;
Hocek, Michal .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) :2278-2284
[7]  
COLLIER A, IN PRESS SYNTH COMMU
[8]   Nucleotide analogues to investigate RNA structure and function [J].
Das, SR ;
Fong, R ;
Piccirilli, JA .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2005, 9 (06) :585-593
[9]   Identification of novel ERK2 substrates through use of an engineered kinase and ATP analogs [J].
Eblen, ST ;
Kumar, NV ;
Shah, K ;
Henderson, MJ ;
Watts, CKW ;
Shokat, KM ;
Weber, MJ .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (17) :14926-14935
[10]   Sonogashira alkynylation of unprotected 8-brominated adenosines and guanosines: fluorescence properties of compact conjugated acetylenes containing a purine ring [J].
Firth, Andrew G. ;
Fairlamb, Ian J. S. ;
Darley, Kate ;
Baumann, Christoph G. .
TETRAHEDRON LETTERS, 2006, 47 (21) :3529-3533