Photolabile group for 5′-OH protection of nucleosides:: synthesis and photodeprotection rate

被引:21
作者
Berroy, P [1 ]
Viriot, ML [1 ]
Carré, MC [1 ]
机构
[1] ENSIC, CNRS, INPL,UMR 7630, GRAPP,Dept Chim Phys React, F-54000 Nancy, France
关键词
photolabile groups; protection of deoxynucleosides; photolysis; DNA array;
D O I
10.1016/S0925-4005(00)00731-0
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
In this paper, we described the properties of a new photolabile group, 2-(3,4-methylenedioxy-6-nitrophenyl)propoxycarbonayl MNPPOC. In spite of moderate yields of synthesis, photolytic properties could be analyzed for 5 ' -OH protected T and dA(iBU). The half-lives (t(1/2)) 11 and 12 s were found, respectively with a good recovery of the corresponding deprotected deoxynucleoside (95-99%). The photolysis rate of this new photolabile group was five-fold faster than the MeNPOC one. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:186 / 189
页数:4
相关论文
共 9 条
[1]  
Fetscher C. A., 1963, ORG SYNTH, V4, P735
[2]   Photolabile protecting groups for nucleosides: Synthesis and photodeprotection rates [J].
Hasan, A ;
Stengele, KP ;
Giegrich, H ;
Cornwell, P ;
Isham, KR ;
Sachleben, RA ;
Pfleiderer, W ;
Foote, RS .
TETRAHEDRON, 1997, 53 (12) :4247-4264
[3]   A NEW SENSITIVE CHEMICAL ACTINOMETER .2. POTASSIUM FERRIOXALATE AS A STANDARD CHEMICAL ACTINOMETER [J].
HATCHARD, CG ;
PARKER, CA .
PROCEEDINGS OF THE ROYAL SOCIETY OF LONDON SERIES A-MATHEMATICAL AND PHYSICAL SCIENCES, 1956, 235 (1203) :518-536
[4]   Model studies for new o-nitrobenzyl photolabile linkers: Substituent effects on the rates of photochemical cleavage [J].
Holmes, CP .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2370-2380
[5]   CHEMICAL ACTINOMETRY [J].
KUHN, HJ ;
BRASLAVSKY, SE ;
SCHMIDT, R .
PURE AND APPLIED CHEMISTRY, 1989, 61 (02) :187-210
[6]   The efficiency of light-directed synthesis of DNA arrays on glass substrates [J].
McGall, GH ;
Barone, AD ;
Diggelmann, M ;
Fodor, SPA ;
Gentalen, E ;
Ngo, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (22) :5081-5090
[7]   COMPARISON OF METHODS FOR PHOTOCHEMICAL PHOSPHORAMIDITE-BASED DNA-SYNTHESIS [J].
PIRRUNG, MC ;
BRADLEY, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) :6270-6276
[8]   TRANSIENT PROTECTION - EFFICIENT ONE-FLASK SYNTHESES OF PROTECTED DEOXYNUCLEOSIDES [J].
TI, GS ;
GAFFNEY, BL ;
JONES, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (05) :1316-1319