Novel solid phase synthesis supports for the preparation of oligonucleotides containing S3'-alkyl amines.

被引:33
作者
McMinn, DL [1 ]
Greenberg, MM [1 ]
机构
[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523
关键词
D O I
10.1016/S0040-4020(96)00053-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
?he synthesis and application of photolabile supports for solid phase oligonucleotide synthesis that release oligonucleotides containing 3'-alkyl amines is described. The alkyl amine functionality can be revealed without removing any other protecting groups throughout the biopolymer. The solid phase synthesis supports do not contain a nucleoside, making it possible to use a single support for the synthesis of oligonucleotides independent of their sequence. Individual solid phase synthesis supports differ according to the length of the alkyl tether between the 4,4'-dimethoxytrityl group which serves as the initiation site for oligonucleotide synthesis and the latent alkyl amine. Eicosameric oligonucleotides are obtained in yields ranging from 70-98% under photolysis conditions that are known to produce less than 3% thymidine thymidine photodimers. Longer oligonucleotides (30 and 40 nucleotides in length) are cleaved from these solid phase synthesis supports in lower yields.
引用
收藏
页码:3827 / 3840
页数:14
相关论文
共 17 条
[11]   A NEW AND VERSATILE REAGENT FOR INCORPORATING MULTIPLE PRIMARY ALIPHATIC-AMINES INTO SYNTHETIC OLIGONUCLEOTIDES [J].
NELSON, PS ;
SHERMANGOLD, R ;
LEON, R .
NUCLEIC ACIDS RESEARCH, 1989, 17 (18) :7179-7186
[12]  
PILLAI VNR, 1987, ORGANIC PHOTOCHEMIST, V9
[13]   STEPWISE REGENERATION AND RECOVERY OF DEOXYRIBONUCLEOSIDE PHOSPHORAMIDITE MONOMERS DURING SOLID-PHASE OLIGONUCLEOTIDE SYNTHESIS [J].
SCREMIN, CL ;
ZHOU, L ;
SRINIVASACHAR, K ;
BEAUCAGE, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08) :1963-1966
[14]   AUTOMATED SYNTHESIS OF OLIGODEOXYRIBONUCLEOSIDE METHYLPHOSPHONATES HAVING [N-(3-AMINOPROP-1-YL)-N-(2-HYDROXYETHYL)-2-AMINOETHYL] PHOSPHATE OR METHYLPHOSPHONIC ACID AT THE 3' END USING A MODIFIED CONTROLLED-PORE GLASS SUPPORT [J].
THADEN, J ;
MILLER, PS .
BIOCONJUGATE CHEMISTRY, 1993, 4 (05) :395-401
[15]   FLUORESCENT DYE PHOSPHORAMIDITE LABELING OF OLIGONUCLEOTIDES [J].
THEISEN, P ;
MCCOLLUM, C ;
UPADHYA, K ;
JACOBSON, K ;
VU, HN ;
ANDRUS, A .
TETRAHEDRON LETTERS, 1992, 33 (35) :5033-5036
[16]  
VENKATESAN H, IN PRESS J ORG CHEM
[17]   SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING 3'-ALKYL CARBOXYLIC-ACIDS USING UNIVERSAL, PHOTOLABILE SOLID-PHASE SYNTHESIS SUPPORTS [J].
YOO, DJ ;
GREENBERG, MM .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3358-3364