A mild, efficient and regioselective enzymatic procedure for 5′-O-benzoylation of 2′-deoxynucleosides

被引：38
作者：
García, J
Fernández, S
Ferrero, M
Sanghvi, YS
Gotor, V
机构：
[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain
[2] Rasayan Inc, Encinitas, CA 92024 USA
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 08期
关键词：
D O I：
10.1016/j.tetlet.2003.12.098
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lipase from Candida antarctica B catalyzes the selective monobenzoylation at the 5'-hydroxyl group of 2'-deoxynucleosides using vinyl benzoate as acyl transfer reagent in quantitative yields. The industrial suitability of this process via the reclaim and reuse of enzyme and vinyl benzoate has been demonstrated. (C) 2003 Elsevier Ltd. All rights reserved.
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收藏
页码：1709 / 1712
页数：4
相关论文
共 23 条
[1]   A mild and highly selective N-benzoylation of cytosine and adenine bases in nucleosides with N-benzoyltetrazole [J].
Bhat, B ;
Sanghvi, YS .
TETRAHEDRON LETTERS, 1997, 38 (51) :8811-8814
[2]   A convenient and practical method for the selective benzoylation of primary hydroxyl groups using microwave heating [J].
Caddick, S ;
McCarroll, AJ ;
Sandham, DA .
TETRAHEDRON, 2001, 57 (29) :6305-6310
[3]   Lipase-catalyzed selective benzoylation of 1,2-diols with vinyl benzoate in organic solvents [J].
Ciuffreda, P ;
Alessandrini, L ;
Terraneo, G ;
Santaniello, E .
TETRAHEDRON-ASYMMETRY, 2003, 14 (20) :3197-3201
[4]   Lipase-catalyzed monoprotection of 1,4-diols in an organic solvent using vinyl benzoate as acyl transfer agent [J].
Ciuffreda, P ;
Casati, S ;
Santaniello, E .
TETRAHEDRON LETTERS, 2003, 44 (18) :3663-3665
[5]  
Crooke ST, 2001, ANTISENSE DRUG TECHNOLOGY: PRINCIPLES, STRATEGIES, AND APPLICATIONS, P1
[6]   Chemoenzymatic transformations in nucleoside chemistry [J].
Ferrero, M ;
Gotor, V .
MONATSHEFTE FUR CHEMIE, 2000, 131 (06) :585-616
[7]   Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides [J].
Ferrero, M ;
Gotor, V .
CHEMICAL REVIEWS, 2000, 100 (12) :4319-+
[8]   Novel enzymatic synthesis of levulinyl protected nucleosides useful for solution phase synthesis of oligonucleotides [J].
García, J ;
Fernández, S ;
Ferrero, M ;
Sanghvi, YS ;
Gotor, V .
TETRAHEDRON-ASYMMETRY, 2003, 14 (22) :3533-3540
[9]   Building blocks for the solution phase synthesis of oligonucleotides:: Regioselective hydrolysis of 3′,5′-Di-O-levulinylnucleosides using an enzymatic approach [J].
García, J ;
Fernández, S ;
Ferrero, M ;
Sanghvi, YS ;
Gotor, V .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4513-4519
[10]   SYNTHESIS OF DEOXYRIBONUCLEOTIDYL(3'-5')ARABINONUCLEOSIDES [J].
GRAY, SH ;
AINSWORTH, CF ;
BELL, CL ;
DANYLUK, SS ;
MACCOSS, M .
NUCLEOSIDES & NUCLEOTIDES, 1983, 2 (05) :435-452
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