NUCLEOTIDES .42. THE 2-DANSYLETHOXYCARBONYL (=2-([5-(DIMETHYLAMINO)NAPHTHALEN-1-YL]SULFONYL )ETHOXYCARBONYL-DNSEOC) GROUP FOR PROTECTION OF THE 5'-HYDROXY FUNCTION IN OLIGORIBONUCLEOTIDE SYNTHESIS

被引：21

作者：

BERGMANN, F ^{[1
]}

PFLEIDERER, W ^{[1
]}

机构：

[1] UNIV KONSTANZ,FAK CHEM,POSTFACH 5560,D-78434 CONSTANCE,GERMANY

来源：

HELVETICA CHIMICA ACTA | 1994年 / 77卷 / 02期

关键词：

D O I：

10.1002/hlca.19940770209

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 2-dansylethoxycarbonyl (Dnseoc) group was employed for protection of the 5'-hydroxy function in oligoribonucleotide synthesis by the phosphoramidite approach using the acid-labile tetrahydro-4-methoxy-2H-pyran-4-yl (Thmp) group for 2'-protection. The syntheses of monomeric building blocks, both phosphoramidites and nucleoside-functionalized supports, are described for the four common nucleosides adenosine, guanosine, cytidine, and uridine, and for the two modified minor nucleosides ribothymidine ( = ribosylthymine) and pseudouridine.

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页码：481 / 501

页数：21

相关论文

共 41 条

[1]

ARENTZEN R, 1975, SYNTHESIS-STUTTGART, P509

[2] DEOXYNUCLEOSIDE PHOSPHORAMIDITES - A NEW CLASS OF KEY INTERMEDIATES FOR DEOXYPOLYNUCLEOTIDE SYNTHESIS [J].

BEAUCAGE, SL ;

CARUTHERS, MH .

TETRAHEDRON LETTERS, 1981, 22 (20) :1859-1862

[3] NUCLEOTIDES .41. THE 2-DANSYLETHOXYCARBONYL (=2-([5-(DIMETHYLAMINO)NAPHTHALEN-1-YL]SULFONYL)ETHOXYCARBONYL DNSEOC) GROUP FOR PROTECTION OF THE 5'-HYDROXY FUNCTION IN OLIGODEOXYRIBONUCLEOTIDE SYNTHESIS [J].

BERGMANN, F ;

PFLEIDERER, W .

HELVETICA CHIMICA ACTA, 1994, 77 (01) :203-215

[4] SYNTHESIS OF THE 3'-TERMINAL HALF OF YEAST ALANINE TRANSFER RIBONUCLEIC-ACID (TRANSFER RNAALA) BY THE PHOSPHOTRIESTER APPROACH IN SOLUTION .1. PREPARATION OF THE NUCLEOSIDE BUILDING-BLOCKS [J].

BROWN, JM ;

CHRISTODOULOU, C ;

JONES, SS ;

MODAK, AS ;

REESE, CB ;

SIBANDA, S ;

UBASAWA, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (10) :1735-1750

[5] INCOMPATIBILITY OF ACID-LABILE 2' AND 5' PROTECTING GROUPS FOR SOLID-PHASE SYNTHESIS OF OLIGORIBONUCLEOTIDES [J].

CHRISTODOULOU, C ;

AGRAWAL, S ;

GAIT, MJ .

TETRAHEDRON LETTERS, 1986, 27 (13) :1521-1522

[6] NUCLEOTIDE CHEMISTRY .8. SYNTHESIS OF OLIGODEOXYNUCLEOTIDES AND OLIGODEOXYNUCLEOTIDE ANALOGS USING PHOSPHORAMIDITE INTERMEDIATES [J].

DORMAN, MA ;

NOBLE, SA ;

MCBRIDE, LJ ;

CARUTHERS, MH .

TETRAHEDRON, 1984, 40 (01) :95-102

[7] SYNTHESIS OF OLOGORIBONUCLEOTIDES .8. PREPARATION OF RIBONUCLEOSIDE 2',5'-BISKETALS [J].

GREEN, DPL ;

RAVINDRANATHAN, T ;

SAFFHILL, R .

TETRAHEDRON, 1970, 26 (04) :1031-+

[8] THE PARA-NITROPHENYLETHYL (NPE) GROUP - A VERSATILE NEW BLOCKING GROUP FOR PHOSPHATE AND AGLYCONE PROTECTION IN NUCLEOSIDES AND NUCLEOTIDES [J].

HIMMELSBACH, F ;

SCHULZ, BS ;

TRICHTINGER, T ;

CHARUBALA, R ;

PFLEIDERER, W .

TETRAHEDRON, 1984, 40 (01) :59-72

[9]

HIMMELSBACH F, 1984, THESIS U KONSTANZ

[10] SYNTHESIS OF OLIGORIBONUCLEOTIDES BY USE OF S,S-DIPHENYL N-MONOMETHOXYTRITYL RIBONUCLEOSIDE 3'-PHOSPHORODITHIOATES [J].

HONDA, S ;

URAKAMI, KI ;

KOURA, K ;

TERADA, K ;

SATO, Y ;

KOHNO, K ;

SEKINE, M ;

HATA, T .

TETRAHEDRON, 1984, 40 (01) :153-163

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