Synthesis of 1-(2′-O-methyl-β-D-ribofuranosyl)-5-nitroindole and its phosphoramidite derivative

被引:5
作者
Gaubert, G [1 ]
Wengel, J [1 ]
机构
[1] Univ So Denmark, Dept Chem, Nucle Acid Ctr, DK-5230 Odense M, Denmark
关键词
5-nitroindole ribonucleoside; phosphoramidite synthesis; universal hybridization; universal base; 2 '-O-Me-RNA monomer;
D O I
10.1016/j.tetlet.2004.05.116
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 1-(2'-O-methyl-beta-D-ribofuranosyl)-5-nitroindole, a new nucleoside containing the universal base 5-nitroindole, and its phosphoramidite derivative for incorporation into oligonucleotides is described. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5629 / 5632
页数:4
相关论文
共 18 条
[1]   AN APPROACH TO THE STRUCTURE DETERMINATION OF NUCLEIC-ACID ANALOGS HYBRIDIZED TO RNA - NMR-STUDIES OF A DUPLEX BETWEEN 2'-OME RNA AND AN OLIGONUCLEOTIDE CONTAINING A SINGLE AMIDE BACKBONE MODIFICATION [J].
BLOMMERS, MJJ ;
PIELES, U ;
DEMESMAEKER, A .
NUCLEIC ACIDS RESEARCH, 1994, 22 (20) :4187-4194
[2]   3,7-DIDEAZAPURINE NUCLEOSIDES - SYNTHESIS AND ANTITUMOR-ACTIVITY OF 1-DEAZATUBERCIDIN AND 2-CHLORO-2'-DEOXY-3,7-DIDEAZAADENOSINE [J].
CRISTALLI, G ;
FRANCHETTI, P ;
GRIFANTINI, M ;
NOCENTINI, G ;
VITTORI, S .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1463-1466
[3]   Synthesis and properties of alpha- and beta-oligodeoxynucleotides containing alpha- and beta-1-(2-O-methyl-d-arabinofuranosyl)thymine [J].
Gotfredsen, CH ;
Jacobsen, JP ;
Wengel, J .
BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (08) :1217-1225
[4]   SYNTHESIS AND HYBRIDIZATION STUDIES ON 2 COMPLEMENTARY NONA(2'-O-METHYL)RIBONUCLEOTIDES [J].
INOUE, H ;
HAYASE, Y ;
IMURA, A ;
IWAI, S ;
MIURA, K ;
OHTSUKA, E .
NUCLEIC ACIDS RESEARCH, 1987, 15 (15) :6131-6148
[5]  
KAMAYA H, 1992, CHEM PHARM BULL, V40, P2792
[6]   THE PREPARATION AND UTILITY OF ETHYL 2-(5'-O-TERT-BUTYLDIMETHYLSILYL-2',3'-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYL)PROPENOATE AS A KEY INTERMEDIATE FOR C-NUCLEOSIDE SYNTHESIS [J].
KANE, PD ;
MANN, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (04) :657-660
[7]   STUDIES ON NUCLEIC-ACID INTERACTIONS .1. STABILITIES OF MINI-DUPLEXES (DG2A4XA4G2.DC2T4YT4C2) AND SELF-COMPLEMENTARY D(GGGAAXYTTCCC) CONTAINING DEOXYINOSINE AND OTHER MISMATCHED BASES [J].
KAWASE, Y ;
IWAI, S ;
INOUE, H ;
MIURA, K ;
OHTSUKA, E .
NUCLEIC ACIDS RESEARCH, 1986, 14 (19) :7727-7736
[8]   OLIGODEOXYNUCLEOTIDES CONTAINING 2'-O-MODIFIED ADENOSINE - SYNTHESIS AND EFFECTS ON STABILITY OF DNA-RNA DUPLEXES [J].
LESNIK, EA ;
GUINOSSO, CJ ;
KAWASAKI, AM ;
SASMOR, H ;
ZOUNES, M ;
CUMMINS, LL ;
ECKER, DJ ;
COOK, PD ;
FREIER, SM .
BIOCHEMISTRY, 1993, 32 (30) :7832-7838
[9]  
LIU H, 1994, BIOTECHNIQUES, V16, P24
[10]   5-NITROINDOLE AS AN UNIVERSAL BASE ANALOG [J].
LOAKES, D ;
BROWN, DM .
NUCLEIC ACIDS RESEARCH, 1994, 22 (20) :4039-4043