NEW SYNTHETIC ROUTES TO PROTECTED PURINE 2'-O-METHYLRIBOSIDE-3'-O-PHOSPHORAMIDITES USING A NOVEL ALKYLATION PROCEDURE

被引：69

作者：

SPROAT, BS ^{[1
]}

BEIJER, B ^{[1
]}

IRIBARREN, A ^{[1
]}

机构：

[1] EUROPEAN MOLEC BIOL LAB,POSTFACH 102209,W-6900 HEIDELBERG,GERMANY

来源：

NUCLEIC ACIDS RESEARCH | 1990年 / 18卷 / 01期

关键词：

D O I：

10.1093/nar/18.1.41

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 highly selective alkylation procedure has been developed enabling new synthetic routes to be established for protected purine 2′-O-methylriboside- 3′-O-phosphoramidites; building blocks for the assembly of 2′-O-methyloligoribonucleotides. The new procedure avoids the use of the highly toxic and potentially explosive reagent diazomethane and is far superior to the use of silver oxide/methyl iodide. Moreover, the use of highly versatile key intermediates will enable the synthesis of a wide variety of base modified analogues as well as other 2′-O-alkylriboside derivatives. © 1990 Oxford University Press.

引用

页码：41 / 49

页数：9

共 33 条

[11]

INOUE H, 1985, NUCLEIC ACIDS RES S, V16, P165

[12]

INOUE H, 1988, NUCLEIC ACIDS RES S, V19, P135

[13] THE PROTECTION OF URACIL AND GUANINE RESIDUES IN OLIGONUCLEOTIDE SYNTHESIS [J].

JONES, SS ;

REESE, CB ;

SIBANDA, S ;

UBASAWA, A .

TETRAHEDRON LETTERS, 1981, 22 (47) :4755-4758

[14] PURINE NUCLEOSIDES .16. SYNTHESIS OF NATURALLY OCCURRING 2'-O-METHYLPURINE RIBONUCLEOSIDES AND RELATED DERIVATIVES [J].

KHWAJA, TA ;

ROBINS, RK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (15) :3640-&

[15] PROBING THE STRUCTURE AND FUNCTION OF U2 SNRNP WITH ANTISENSE OLIGONUCLEOTIDES MADE OF 2'-OME RNA [J].

LAMOND, AI ;

SPROAT, B ;

RYDER, U ;

HAMM, J .

CELL, 1989, 58 (02) :383-390

[16]

MARKIEWICZ WT, 1979, J CHEM RES-S, P24

[17] ACTION OF DIAZOMETHANE ON RIBONUCLEOSIDES - PREPARATION OF RIBONUCLEOSIDE 2'- AND 3'-METHYL ETHERS [J].

MARTIN, DMG ;

REESE, CB ;

STEPHENS.GF .

BIOCHEMISTRY, 1968, 7 (04) :1406-&

[18] AMIDINE PROTECTING GROUPS FOR OLIGONUCLEOTIDE SYNTHESIS .16. [J].

MCBRIDE, LJ ;

KIERZEK, R ;

BEAUCAGE, SL ;

CARUTHERS, MH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2040-2048

[19]

MUKAI S, 1988, NUCLEIC ACIDS RES S, V19, P117

[20] SYNTHESIS OF CONGENERS OF ADENOSINE RESISTANT TO DEAMINATION BY ADENOSINE-DEAMINASE [J].

NAIR, V ;

PURDY, DF ;

SELLS, TB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (13) :878-879

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