Synthesis of C4-linked imidazole ribonudeoside phosphoramidite with pivaloyloxymethyl (POM) group

被引:22
作者
Araki, L
Harusawa, S
Yamaguchi, M
Yonezawa, S
Taniguchi, N
Lilley, DMJ
Zhao, ZY
Kurihara, T
机构
[1] Osaka Univ Pharmaceut Sci, Takatsuki, Osaka 5691094, Japan
[2] Univ Dundee, Dept Biochem, Dundee DD1 5EH, Scotland
关键词
D O I
10.1016/j.tetlet.2004.01.132
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel C4-linked imidazole ribonucleoside phosphoramidite was designed and successfully synthesized starting from tribenzylribofuranosylimidazole. This phosphoramidite product enables incorporation of the imidazole moiety into an RNA sequence and hence allows study of its role in the general acid and base catalysis of ribozymes. Pivaloyloxymethyl (POM) was first introduced as an N-protecting group for the imidazole ribonucleoside that can be readily removed under mild basic condition. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2657 / 2661
页数:5
相关论文
共 23 条
[1]  
[Anonymous], PROTECTIVE GROUPS OR
[2]   SYNTHESIS OF 2'-DEOXY-BETA-D-RIBOFURANOSYL IMIDAZOLE AND THIAZOLE C-NUCLEOSIDES [J].
BERGSTROM, DE ;
ZHANG, PM ;
ZHOU, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (20) :3029-3034
[3]  
CARUTHERS MH, 1987, METHOD ENZYMOL, V154, P287
[4]   STUDIES IN THE PROTECTION OF PYRROLE AND INDOLE-DERIVATIVES [J].
DHANAK, D ;
REESE, CB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (12) :2181-2186
[5]   NEW CATALYSTS AND PROCEDURES FOR THE DIMETHOXYTRITYLATION AND SELECTIVE SILYLATION OF RIBONUCLEOSIDES [J].
HAKIMELAHI, GH ;
PROBA, ZA ;
OGILVIE, KK .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (09) :1106-1113
[6]   Efficient and beta-stereoselective synthesis of 4(5)-(beta-D-ribofuranosyl)- and 4(5)-(2-deoxyribofuranosyl)imidazoles [J].
Harusawa, S ;
Murai, Y ;
Moriyama, H ;
Imazu, T ;
Ohishi, H ;
Yoneda, R ;
Kurihara, T .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4405-4411
[7]   ALLYLIC REARRANGEMENT FROM O6 TO N-3 AND N-7 OF GUANINE BLOCKED AT C-8 [J].
HOLMES, BN ;
LEONARD, NJ .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (03) :568-571
[8]   A1 adenosine receptor antagonists as ligands for positron emission tomography (PET) and single-photon emission tomography (SPET) [J].
Holschbach, MH ;
Fein, T ;
Krummeich, C ;
Lewis, RG ;
Wutz, W ;
Schwabe, U ;
Unterlugauer, D ;
Olsson, RA .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (04) :555-563
[9]   MIGRATION OF TERT-BUTYLDIMETHYLSILYL PROTECTING GROUPS [J].
JONES, SS ;
REESE, CB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (11) :2762-2764
[10]   A NEW PROTECTING TACTICS FOR THE URACIL RESIDUE IN OLIGORIBONUCLEOTIDE SYNTHESIS [J].
KAMIMURA, T ;
MASEGI, T ;
URAKAMI, K ;
HONDA, S ;
SEKINE, M ;
HATA, T .
CHEMISTRY LETTERS, 1983, (07) :1051-1054