Synthesis of pentathymidylate using a 4-monomethoxytritylthio (MMTrS) group as a 5′-hydroxyl protecting group:: toward oligonucleotide synthesis without acid treatment

被引：6

作者：

Seio, K ^{[1
]}

Sekine, M ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Life Sci, Yokohama, Kanagawa 2268501, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 49期

基金：

日本学术振兴会;

关键词：

oligonucleotide synthesis; protective group; sulfenic acid esters;

D O I：

10.1016/S0040-4039(01)01873-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A phosphoramidite unit having 4-monomethoxytritylthio as a new 5'-hydroxyl protecting group was prepared and employed in oligonucleotide synthesis. The new phosphoramidite enabled the synthesis of oligonucleotides without the use of acids such as TFA or DCA. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8657 / 8660

页数：4

共 12 条

[1] A reinvestigation of sulfenyl groups as amino protecting groups for the synthesis of oligonucleotides on solid support by phosphoramidite chemistry
Alvarez, K
Tworkowski, I
Vasseur, JJ
Imbach, JL
Rayner, B
[J]. NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1998, 17 (1-3) : 365 - 378
[2] SOME ASPECTS OF THE REACTION OF ARENESULFENYL CHLORIDES WITH HYDROXYL FUNCTIONS OF RIBONUCLEOSIDES
BAZIN, H
HEIKKILA, J
CHATTOPADHYAYA, J
[J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1985, 39 (05): : 391 - 400
[3] ADVANCES IN THE SYNTHESIS OF OLIGONUCLEOTIDES BY THE PHOSPHORAMIDITE APPROACH
BEAUCAGE, SL
IYER, RP
[J]. TETRAHEDRON, 1992, 48 (12) : 2223 - 2311
[4] A NEW 5'-PROTECTING GROUP FOR USE IN SOLID-PHASE SYNTHESIS OF OLIGORIBONUCLEOTIDES
CHRISTODOULOU, C
AGRAWAL, S
GAIT, MJ
[J]. NUCLEOSIDES & NUCLEOTIDES, 1987, 6 (1-2): : 341 - 344
[5] THE CHEMISTRY OF SULFENAMIDES
CRAINE, L
RABAN, M
[J]. CHEMICAL REVIEWS, 1989, 89 (04) : 689 - 712
[6] THE TDE SULFENYL GROUP AS A PROTECTIVE GROUP FOR AMINES
NETSCHER, T
WELLER, T
[J]. TETRAHEDRON, 1991, 47 (38) : 8145 - 8154
[7] SEIO K, 1993, J CHEM SOC P1, P3087
[8] POLYMER SUPPORT OLIGONUCLEOTIDE SYNTHESIS .18. USE OF BETA-CYANOETHYL-N,N-DIALKYLAMINO-/N-MORPHOLINO PHOSPHORAMIDITE OF DEOXYNUCLEOSIDES FOR THE SYNTHESIS OF DNA FRAGMENTS SIMPLIFYING DEPROTECTION AND ISOLATION OF THE FINAL PRODUCT
SINHA, ND
BIERNAT, J
MCMANUS, J
KOSTER, H
[J]. NUCLEIC ACIDS RESEARCH, 1984, 12 (11) : 4539 - 4557
[9] TRIPHENYLMETHANESULFENYL GROUP - A NEW PROTECTING GROUP FOR THE URACIL RESIDUE IN OLIGORIBONUCLEOTIDE SYNTHESIS
TAKAKU, H
IMAI, K
NAGAI, M
[J]. CHEMISTRY LETTERS, 1988, (05) : 857 - 860
[10] UEKI M, 1994, SYNTHESIS-STUTTGART, P21

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