SYNTHESIS AND APPLICATIONS OF OLIGORIBONUCLEOTIDES WITH SELECTED 2'-O-METHYLATION USING THE 2'-O-[1-(2-FLUOROPHENYL)-4-METHOXYPIPERIDIN-4-YL] PROTECTING GROUP

被引:51
作者
BEIJER, B [1 ]
SULSTON, I [1 ]
SPROAT, BS [1 ]
RIDER, P [1 ]
LAMOND, AI [1 ]
NEUNER, P [1 ]
机构
[1] EUROPEAN MOLEC BIOL LAB,POSTFACH 102209,W-6900 HEIDELBERG,GERMANY
关键词
D O I
10.1093/nar/18.17.5143
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
The synthesis of base protected 5′-O-dimethoxytrityl-2′-O-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl]-3′-O-(2-cyanoethyl N,N-diisopropylphosphoramidites) is described, using phenoxyacetyl protection for the exocyclic amino groups of guanosine and adenosine and acetyl protection of the amino group of cytidine. High yield assembly of these building blocks into oligoribonucleotides on aminopropyl controlled pore glass was achieved using 5-(4-nitrophenyl)-1H-tetrazole as activator. Mixed sequences containing selected 2′-O-methylation were also synthesised and their significance for the study of RNA biochemistry is discussed. © 1990 Oxford University Press.
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页码:5143 / 5151
页数:9
相关论文
共 53 条
[11]   SUBSTITUTED 5-PHENYLTETRAZOLES - IMPROVED ACTIVATORS OF DEOXYNUCLEOSIDE PHOSPHORAMIDITES IN DEOXYOLIGONUCLEOTIDE SYNTHESIS [J].
FROEHLER, BC ;
MATTEUCCI, MD .
TETRAHEDRON LETTERS, 1983, 24 (31) :3171-3174
[12]   NUCLEOSIDE H-PHOSPHONATES .3. CHEMICAL SYNTHESIS OF OLIGODEOXYRIBONUCLEOTIDES BY THE HYDROGENPHOSPHONATE APPROACH [J].
GAREGG, PJ ;
LINDH, I ;
REGBERG, T ;
STAWINSKI, J ;
STROMBERG, R ;
HENRICHSON, C .
TETRAHEDRON LETTERS, 1986, 27 (34) :4051-4054
[13]   5'-LEVULINYL AND 2'-TETRAHYDROFURANYL PROTECTION FOR THE SYNTHESIS OF OLIGORIBONUCLEOTIDES BY THE PHOSPHORAMIDITE APPROACH [J].
IWAI, S ;
OHTSUKA, E .
NUCLEIC ACIDS RESEARCH, 1988, 16 (20) :9443-9456
[14]   SYNTHESIS OF OLIGORIBONUCLEOTIDES BY THE PHOSPHORAMIDITE APPROACH USING 5'-LEVULINYL AND 2'-TETRAHYDROFURANYL PROTECTION [J].
IWAI, S ;
OHTSUKA, E .
TETRAHEDRON LETTERS, 1988, 29 (42) :5383-5386
[15]  
IWAI S, 1987, NUCLEIC ACIDS RES, V15, P3761
[16]   POLYMER-SUPPORTED RNA-SYNTHESIS AND ITS APPLICATION TO TEST THE NEAREST-NEIGHBOR MODEL FOR DUPLEX STABILITY [J].
KIERZEK, R ;
CARUTHERS, MH ;
LONGFELLOW, CE ;
SWINTON, D ;
TURNER, DH ;
FREIER, SM .
BIOCHEMISTRY, 1986, 25 (24) :7840-7846
[17]   DESIGN OF RNA ENZYMES DISTINGUISHING A SINGLE BASE MUTATION IN RNA [J].
KOIZUMI, M ;
HAYASE, Y ;
IWAI, S ;
KAMIYA, H ;
INOUE, H ;
OHTSUKA, E .
NUCLEIC ACIDS RESEARCH, 1989, 17 (17) :7059-7071
[18]   SOLID-PHASE SYNTHESIS OF OLIGORIBONUCLEOTIDES USING 9-FLUORENYLMETHOXYCARBONYL (FMOC) FOR 5'-HYDROXYL PROTECTION [J].
LEHMANN, C ;
XU, YZ ;
CHRISTODOULOU, C ;
TAN, ZK ;
GAIT, MJ .
NUCLEIC ACIDS RESEARCH, 1989, 17 (07) :2379-2390
[19]  
MARKIEWICZ WT, 1979, J CHEM RES-S, P24
[20]   NUCLEOTIDE CHEMISTRY .4. SYNTHESIS OF DEOXYOLIGONUCLEOTIDES ON A POLYMER SUPPORT [J].
MATTEUCCI, MD ;
CARUTHERS, MH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3185-3191