INCORPORATION OF (R) AND (S)-3',4'-SECO-THYMIDINE INTO OLIGODEOXYNUCLEOTIDES - HYBRIDIZATION PROPERTIES AND ENZYMATIC STABILITY

被引:41
作者
NIELSEN, P
KIRPEKAR, F
WENGEL, J
机构
[1] ODENSE UNIV,DEPT CHEM,DK-5230 ODENSE,DENMARK
[2] ODENSE UNIV,DEPT MOLEC BIOL,DK-5230 ODENSE,DENMARK
关键词
D O I
10.1093/nar/22.5.703
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
Novel flexible oligodeoxynucleotide analogues containing (R)- and (S)-3',4'-seco-thymidine were synthesized on an automated DNA-synthesizer using the phosphoramidite approach. Oligodeoxynucleotide analogues (17-mers) having one or three modifications in the middle or one or two modifications in the ends were evaluated with respect to hybridization properties and enzymatic stability. 3'-End-modified oligomers were stable towards 3'-exonuclease degradation and displayed acceptable hybridization properties.
引用
收藏
页码:703 / 710
页数:8
相关论文
共 37 条
  • [1] INCORPORATION OF HEXOSE NUCLEOSIDE ANALOGS INTO OLIGONUCLEOTIDES - SYNTHESIS, BASE-PAIRING PROPERTIES AND ENZYMATIC STABILITY
    AUGUSTYNS, K
    VANDENDRIESSCHE, F
    VANAERSCHOT, A
    BUSSON, R
    URBANKE, C
    HERDEWIJN, P
    [J]. NUCLEIC ACIDS RESEARCH, 1992, 20 (18) : 4711 - 4716
  • [2] INFLUENCE OF THE INCORPORATION OF (S)-9-(3,4-DIHYDROXY-BUTYL)ADENINE ON THE ENZYMATIC STABILITY AND BASE-PAIRING PROPERTIES OF OLIGODEOXYNUCLEOTIDES
    AUGUSTYNS, K
    VANAERSCHOT, A
    VANSCHEPDAEL, A
    URBANKE, C
    HERDEWIJN, P
    [J]. NUCLEIC ACIDS RESEARCH, 1991, 19 (10) : 2587 - 2593
  • [3] 4'-THIO-OLIGO-BETA-D-RIBONUCLEOTIDES - SYNTHESIS OF BETA-4'-THIO-OLIGOURIDYLATES, NUCLEASE RESISTANCE, BASE-PAIRING PROPERTIES, AND INTERACTION WITH HIV-1 REVERSE-TRANSCRIPTASE
    BELLON, L
    BARASCUT, JL
    MAURY, G
    DIVITA, G
    GOODY, R
    IMBACH, JL
    [J]. NUCLEIC ACIDS RESEARCH, 1993, 21 (07) : 1587 - 1593
  • [4] BEUCAGE SL, 1993, TETRAHEDRON, V49, P6123
  • [5] SOLID-PHASE SYNTHESIS OF OLIGODEOXYRIBONUCLEOSIDE PHOSPHORODITHIOATES FROM THIOPHOSPHORAMIDITES
    BJERGARDE, K
    DAHL, O
    [J]. NUCLEIC ACIDS RESEARCH, 1991, 19 (21) : 5843 - 5850
  • [6] SYNTHESIS OF OLIGODEOXYNUCLEOSIDE PHOSPHORODITHIOATES VIA THIOAMIDITES
    BRILL, WKD
    TANG, JY
    MA, YX
    CARUTHERS, MH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (06) : 2321 - 2322
  • [7] SUGAR MODIFIED OLIGONUCLEOTIDES .2. SOLID-PHASE SYNTHESIS OF NUCLEASE RESISTANT ALPHA-ANOMERIC URIDYLATES AS POTENTIAL ANTISENSE AGENTS
    DEBART, F
    RAYNER, B
    IMBACH, JL
    [J]. TETRAHEDRON LETTERS, 1990, 31 (25) : 3537 - 3540
  • [8] WHY PENTOSE AND NOT HEXOSE NUCLEIC-ACIDS .1. INTRODUCTION TO THE PROBLEM, CONFORMATIONAL-ANALYSIS OF OLIGONUCLEOTIDE SINGLE STRANDS CONTAINING 2',3'-DIDEOXYGLUCOPYRANOSYL BUILDING-BLOCKS (HOMO-DNA), AND REFLECTIONS ON THE CONFORMATION OF A-DNA AND B-DNA
    ESCHENMOSER, A
    DOBLER, M
    [J]. HELVETICA CHIMICA ACTA, 1992, 75 (01) : 218 - 259
  • [9] SPECIFIC REGULATION OF GENE-EXPRESSION BY ANTISENSE, SENSE AND ANTIGENE NUCLEIC-ACIDS
    HELENE, C
    TOULME, JJ
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA, 1990, 1049 (02) : 99 - 125
  • [10] SYNTHESIS OF 2'-DEOXY-2'-FLUORO-D-ARABINOPYRANOSYL NUCLEOSIDES AND THEIR 3',4'-SECO ANALOGS
    HERDEWIJN, P
    VANAERSCHOT, A
    BUSSON, R
    CLAES, P
    DECLERCQ, E
    [J]. NUCLEOSIDES & NUCLEOTIDES, 1991, 10 (07): : 1525 - 1549