New photolabile protecting groups in nucleoside and nucleotide chemistry -: Synthesis, cleavage mechanisms and applications

被引:48
作者
Giegrich, H [1 ]
Eisele-Bühler, S [1 ]
Hermann, C [1 ]
Kvasyuk, E [1 ]
Charubala, R [1 ]
Pfleiderer, W [1 ]
机构
[1] Univ Konstanz, Fak Chem, D-78434 Constance, Germany
来源
NUCLEOSIDES & NUCLEOTIDES | 1998年 / 17卷 / 9-11期
关键词
D O I
10.1080/07328319808004738
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
New photolabile protecting groups have been found in the 2-(2-nitrophenyl)ethoxycarbonyl and the 2-(2-nitrophenyl)ethylsulfonyl group, respectively. The influence of substituents at the phenyl ring as well as the side-chain has been investigated regarding the photolysis rates on irradiation at 365 mn. beta-Branching in the side-chain leads to highly increased rates of photodeprotection. A new type of photocleavage mechanism consisting of a photoinduced beta-elimination process is proposed.
引用
收藏
页码:1987 / 1996
页数:10
相关论文
共 22 条
[1]   A NOVEL METHOD FOR NUCLEIC-ACID SEQUENCE DETERMINATION [J].
BAINS, W ;
SMITH, GC .
JOURNAL OF THEORETICAL BIOLOGY, 1988, 135 (03) :303-307
[2]  
DRMANAC R, 1989, GENOMICS, V4, P114
[3]   LIGHT-DIRECTED, SPATIALLY ADDRESSABLE PARALLEL CHEMICAL SYNTHESIS [J].
FODOR, SPA ;
READ, JL ;
PIRRUNG, MC ;
STRYER, L ;
LU, AT ;
SOLAS, D .
SCIENCE, 1991, 251 (4995) :767-773
[4]   NEW PHOTOCHEMICALLY LABILE PROTECTING GROUP FOR PHOSPHATES [J].
FURUTA, T ;
TORIGAI, H ;
OSAWA, T ;
IWAMURA, M .
CHEMISTRY LETTERS, 1993, (07) :1179-1182
[5]   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
[6]  
HAYASHI M, 1985, THESIS KONSTANZ U
[7]   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
[8]   COMBINATORIAL CHEMISTRY - APPLICATIONS OF LIGHT-DIRECTED CHEMICAL SYNTHESIS [J].
JACOBS, JW ;
FODOR, SPA .
TRENDS IN BIOTECHNOLOGY, 1994, 12 (01) :19-26
[9]   AN OLIGONUCLEOTIDE HYBRIDIZATION APPROACH TO DNA SEQUENCING [J].
KHRAPKO, KR ;
LYSOV, YP ;
KHORLYN, AA ;
SHICK, VV ;
FLORENTIEV, VL ;
MIRZABEKOV, AD .
FEBS LETTERS, 1989, 256 (1-2) :118-122
[10]  
LYSOV YP, 1988, DOKL AKAD NAUK SSSR, V303, P1508