New carbamate supports for the preparation of 3'-amino-modified oligonucleotides

被引:17
作者
Avino, A
Garcia, RG
Albericio, F
Mann, M
Wilm, M
Neubauer, G
Eritja, R
机构
[1] CSIC,CTR INVEST & DESARROLLO,DEPT MOL BIOL,E-08034 BARCELONA,SPAIN
[2] EUROPEAN MOL BIOL LAB,D-69117 HEIDELBERG,GERMANY
[3] UNIV BARCELONA,FAC QUIM,DEPT ORGAN CHEM,E-08028 BARCELONA,SPAIN
关键词
D O I
10.1016/0968-0896(96)00156-3
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
A novel approach for the preparation of oligonucleotides carrying amino groups at the 3'-end is described. Several CPG supports having aminoalkyl groups and 3'-amino-2', 3'-dideoxynucleosides linked through base-labile carbamate linkages such as 2-(2-nitrophenyl)ethoxycarbonyl and fluorenylmethoxycarbonyl were prepared using two different strategies. These supports are compatible to the standard solid phase phosphite-triester methodology and yield oligonucleotides containing amino groups at the 3'-end. Several properties of the 3'-amino oligonucleotides, such as nuclease resistance, hybridization, and preparation of oligonucleotide conjugates are discussed. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:1649 / 1658
页数:10
相关论文
共 28 条
[1]   PREPARATION OF OLIGONUCLEOTIDE-DEXAMETHASONE CONJUGATES [J].
ACEDO, M ;
TARRASON, G ;
PIULATS, J ;
MANN, M ;
WILM, M ;
ERITJA, R .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (15) :1577-1580
[2]  
Agrawal S, 1994, Methods Mol Biol, V26, P93
[3]   A NEW ACHIRAL REAGENT FOR THE INCORPORATION OF MULTIPLE AMINO-GROUPS INTO OLIGONUCLEOTIDES [J].
BEHRENS, C ;
PETERSEN, KH ;
EGHOLM, M ;
NIELSEN, J ;
BUCHARDT, O ;
DAHL, O .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (16) :1785-1790
[4]   SYNTHESIS OF OLIGODEOXYRIBONUCLEOTIDE N3'-]P5' PHOSPHORAMIDATES [J].
CHEN, JK ;
SCHULTZ, RG ;
LLOYD, DH ;
GRYAZNOV, SM .
NUCLEIC ACIDS RESEARCH, 1995, 23 (14) :2661-2668
[5]   RATIONAL DESIGN OF POINT MUTATION-SELECTIVE ANTISENSE DNA TARGETED TO CODON-12 OF HA-RAS MESSENGER-RNA IN HUMAN-CELLS [J].
DUROUX, I ;
GODARD, G ;
BOIDOTFORGET, M ;
SCHWAB, G ;
HELENE, C ;
SAISONBEHMOARAS, T .
NUCLEIC ACIDS RESEARCH, 1995, 23 (17) :3411-3418
[6]   A SYNTHETIC PROCEDURE FOR THE PREPARATION OF OLIGONUCLEOTIDES WITHOUT USING AMMONIA AND ITS APPLICATION FOR THE SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING O-4-ALKYL THYMIDINES [J].
ERITJA, R ;
ROBLES, J ;
AVINO, A ;
ALBERICIO, F ;
PEDROSO, E .
TETRAHEDRON, 1992, 48 (20) :4171-4182
[7]   SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING THE ABASIC SITE MODEL-COMPOUND 1,4-ANHYDRO-2-DEOXY-D-RIBITOL [J].
ERITJA, R ;
WALKER, PA ;
RANDALL, SK ;
GOODMAN, MF ;
KAPLAN, BE .
NUCLEOSIDES & NUCLEOTIDES, 1987, 6 (04) :803-814
[8]   FACILE PREPARATION OF NUCLEASE RESISTANT 3' MODIFIED OLIGODEOXYNUCLEOTIDES [J].
GAMPER, HB ;
REED, MW ;
COX, T ;
VIROSCO, JS ;
ADAMS, AD ;
GALL, AA ;
SCHOLLER, JK ;
MEYER, RB .
NUCLEIC ACIDS RESEARCH, 1993, 21 (01) :145-150
[9]   NUCLEOTIDE SYNTHESIS .4. PHOSPHORYLATED 3'-AMINO-3'-DEOXYTHYMIDINE AND 5'-AMINO-5'-DEOXYTHYMIDINE AND DERIVATIVES [J].
GLINSKI, RP ;
KHAN, MS ;
KALAMAS, RL ;
SPORN, MB .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (25) :4299-4305
[10]   SYNTHESIS AND PROPERTIES OF OLIGONUCLEOTIDES CONTAINING AMINODEOXYTHYMIDINE UNITS [J].
GRYAZNOV, SM ;
LETSINGER, RL .
NUCLEIC ACIDS RESEARCH, 1992, 20 (13) :3403-3409