SYNTHESIS OF OLIGODEOXYNUCLEOTIDES CONTAINING THE C-NUCLEOSIDE AND 2'-DEOXY-2'-FLUORO-ARA-NUCLEOSIDE MOIETIES BY THE H-PHOSPHONATE METHOD

被引：24

作者：

ROSENBERG, I ^{[1
]}

SOLER, JF ^{[1
]}

TOCIK, Z ^{[1
]}

REN, WY ^{[1
]}

CISZEWSKI, LA ^{[1
]}

KOIS, P ^{[1
]}

PANKIEWICZ, KW ^{[1
]}

SPASSOVA, M ^{[1
]}

WATANABE, KA ^{[1
]}

机构：

[1] CORNELL UNIV,MEM SLOAN KETTERING CANC CTR,GRAD SCH MED SCI,NEW YORK,NY 10021

来源：

NUCLEOSIDES & NUCLEOTIDES | 1993年 / 12卷 / 3-4期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1080/07328319308017834

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 module type, computer-controlled, multipurpose synthesizer displaying a novel device for the transport of liquids, was constructed and used in the synthesis of oligomers containing some C-nucleosides and 2'-deoxy-2'-fluoro-ara-nucleoside moieties. H-Phosphonate method was applied in terms of a further adjustment of construction features of the synthesizer versus chemistry of the process. Results of preliminary studies on the effects of the modified nucleosides on the stability of duplexes showed a clear tendency of destabilization of duplexes in the case of C-nucleosides while fluorinated nucleosides in most cases stabilize the formed duplexes.

引用

页码：381 / 401

页数：21

共 31 条

[1] NOVEL ACTIVATING AND CAPPING REAGENTS FOR IMPROVED HYDROGEN-PHOSPHONATE DNA-SYNTHESIS [J].

ANDRUS, A ;

EFCAVITCH, JW ;

MCBRIDE, LJ ;

GIUSTI, B .

TETRAHEDRON LETTERS, 1988, 29 (08) :861-864

[2] OLIGONUCLEOTIDIC COMPOUNDS .73. AUTOMATED CHLORIDITE AND AMIDITE SYNTHESIS OF OLIGODEOXYRIBONUCLEOTIDES ON A LONG-CHAIN SUPPORT USING AMIDINE PROTECTED PURINE NUCLEOSIDES [J].

ARNOLD, L ;

TOCIK, Z ;

BRADKOVA, E ;

HOSTOMSKY, Z ;

PACES, V ;

SMRT, J .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1989, 54 (02) :523-532

[3]

ATKINSON T, 1984, OLIGONUCLEOTIDE SYNT, P46

[4] STUDIES ON NUCLEOTIDE CHEMISTRY .15. SYNTHESIS OF OLIGODEOXYNUCLEOTIDES USING AMIDINE PROTECTED NUCLEOSIDES [J].

CARUTHERS, MH ;

MCBRIDE, LJ ;

BRACCO, LP ;

DUBENDORFF, JW .

NUCLEOSIDES & NUCLEOTIDES, 1985, 4 (1-2) :95-105

[5] NUCLEOSIDES .119. 2'-DEOXY-PSI-ISOCYTIDINE, 2'-DEOXY-PSI-URIDINE, AND 2'-DEOXY-1-METHYL-PSI-URIDINE - ISOSTERES OF DEOXYCYTIDINE, DEOXYURIDINE AND THYMIDINE [J].

CHU, CK ;

REICHMAN, U ;

WATANABE, KA ;

FOX, JJ .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (06) :1119-1121

[6] A SIMPLE AND STABLE SILICA-GEL SUPPORT FOR THE OLIGODEOXYRIBONUCLEOTIDE SYNTHESIS [J].

DEUTSCH, J ;

COHEN, S ;

WEISZ, M ;

KATZHENDLER, J .

NUCLEOSIDES & NUCLEOTIDES, 1986, 5 (03) :325-330

[7] NMR-STUDY AND IMPROVEMENT OF H-PHOSPHONATE OLIGONUCLEOTIDE SYNTHESIS [J].

EFIMOV, VA ;

DUBEY, IY ;

CHAKHMAKHCHEVA, OG .

NUCLEOSIDES & NUCLEOTIDES, 1990, 9 (03) :473-477

[8] SYNTHESIS OF DNA VIA DEOXYNUCLEOSIDE H-PHOSPHONATE INTERMEDIATES [J].

FROEHLER, BC ;

NG, PG ;

MATTEUCCI, MD .

NUCLEIC ACIDS RESEARCH, 1986, 14 (13) :5399-5407

[9] H-PHOSPHONATE OLIGONUCLEOTIDE SYNTHESIS ON A POLYETHYLENE-GLYCOL POLYSTYRENE COPOLYMER [J].

GAO, HT ;

GAFFNEY, BL ;

JONES, RA .

TETRAHEDRON LETTERS, 1991, 32 (40) :5477-5480

[10] NUCLEOSIDE H-PHOSPHONATES .5. THE MECHANISM OF HYDROGENPHOSPHONATE DIESTER FORMATION USING ACYL CHLORIDES AS COUPLING AGENTS IN OLIGONUCLEOTIDE SYNTHESIS BY THE HYDROGENPHOSPHONATE APPROACH [J].

GAREGG, PJ ;

REGBERG, T ;

STAWINSKI, J ;

STROMBERG, R .

NUCLEOSIDES & NUCLEOTIDES, 1987, 6 (03) :655-662

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