A CONVENIENT APPROACH TO THE SYNTHESIS OF MEDIUM SIZE OLIGODEOXYRIBONUCLEOTIDES BY IMPROVED NEW PHOSPHITE METHOD

被引：18

作者：

HOSAKA, H ^{[1
]}

SUZUKI, Y ^{[1
]}

SATO, H ^{[1
]}

GUGKIM, S ^{[1
]}

TAKAKU, H ^{[1
]}

机构：

[1] CHIBA INST TECHNOL,DEPT IND CHEM,NARASHINO,CHIBA 275,JAPAN

来源：

NUCLEIC ACIDS RESEARCH | 1991年 / 19卷 / 11期

关键词：

D O I：

10.1093/nar/19.11.2935

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：

Improvement of the new phosphite method for the synthesis of oligodeoxyribonucleotides using the deoxyribonucleoside 3'-bis(1,1,1,3,3,3- hexafluoro-2-propyl) phosphite unit has been carried out via the hydrolysis and capping steps, without any side reaction products. The new phosphite unit and capping agent, bis(1,1,1,3,3,3-hexafluoro-2-propyl)-2-propyl phosphite, is readily activated by N-methylimdazole under very mild condition on a solid support. This operation involves a one pot reaction, which is an advantage over both the phosphite and H- phosphonate approaches. The mechanism of internucleotidic bond formation of the new phosphite method is also discussed.

引用

页码：2935 / 2940

页数：6

共 29 条

[1] INHIBITION OF VESICULAR STOMATITIS-VIRUS PROTEIN-SYNTHESIS AND INFECTION BY SEQUENCE-SPECIFIC OLIGODEOXYRIBONUCLEOSIDE METHYLPHOSPHONATES
AGRIS, CH
BLAKE, KR
MILLER, PS
REDDY, MP
TSO, POP
[J]. BIOCHEMISTRY, 1986, 25 (20) : 6268 - 6275
[2] NOVEL ACTIVATING AND CAPPING REAGENTS FOR IMPROVED HYDROGEN-PHOSPHONATE DNA-SYNTHESIS
ANDRUS, A
EFCAVITCH, JW
MCBRIDE, LJ
GIUSTI, B
[J]. TETRAHEDRON LETTERS, 1988, 29 (08) : 861 - 864
[3] INSITU ACTIVATION OF BIS-DIALKYLAMINOPHOSPHINES - A NEW METHOD FOR SYNTHESIZING DEOXYOLIGONUCLEOTIDES ON POLYMER SUPPORTS
BARONE, AD
TANG, JY
CARUTHERS, MH
[J]. NUCLEIC ACIDS RESEARCH, 1984, 12 (10) : 4051 - 4061
[4] DEOXYNUCLEOSIDE PHOSPHORAMIDITES - A NEW CLASS OF KEY INTERMEDIATES FOR DEOXYPOLYNUCLEOTIDE SYNTHESIS
BEAUCAGE, SL
CARUTHERS, MH
[J]. TETRAHEDRON LETTERS, 1981, 22 (20) : 1859 - 1862
[5] PREPARATION AND NUCLEAR MAGNETIC-RESONANCE STUDIES OF PENTA-COORDINATED PHOSPHORUS-COMPOUNDS CONTAINING HEXAFLUORISOPROPOXY GROUPS
DENNEY, DB
DENNEY, DZ
HAMMOND, PJ
LIU, LT
WANG, YP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (13) : 2159 - 2164
[6] SYNTHESIS OF DNA VIA DEOXYNUCLEOSIDE H-PHOSPHONATE INTERMEDIATES
FROEHLER, BC
NG, PG
MATTEUCCI, MD
[J]. NUCLEIC ACIDS RESEARCH, 1986, 14 (13) : 5399 - 5407
[7] GAREGG PJ, 1985, CHEM SCRIPTA, V25, P280
[8] NUCLEOSIDE H-PHOSPHONATES .3. CHEMICAL SYNTHESIS OF OLIGODEOXYRIBONUCLEOTIDES BY THE HYDROGENPHOSPHONATE APPROACH
GAREGG, PJ
LINDH, I
REGBERG, T
STAWINSKI, J
STROMBERG, R
HENRICHSON, C
[J]. TETRAHEDRON LETTERS, 1986, 27 (34) : 4051 - 4054
[9] GAREGG PJ, 1986, TETRAHEDRON LETT, V27, P469
[10] Gerrard W., 1973, ORGANIC PHOSPHORUS C, V5, P21

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