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

[21] A CONVENIENT PREPARATION OF TETRAHYDRO-4H-PYRAN-4-ONE [J].

OWEN, GR ;

REESE, CB .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (17) :2401-+

[22] NUCLEOSIDES .121. IMPROVED AND GENERAL-SYNTHESIS OF 2'-DEOXY C-NUCLEOSIDES - SYNTHESIS OF 5-(2-DEOXY-BETA-D-ERYTHRO-PENTOFURANOSYL)URACIL, 5-(2-DEOXY-BETA-D-ERYTHRO-PENTOFURANOSYL)1-METHYLURACIL, 5-(2-DEOXY-BETA-D-ERYTHRO-PENTOFURANOSYL)1,3-DIMETHYLURACIL, AND 5-(2-DEOXY-BETA-D-ERYTHRO-PENTOFURANOSYL)ISOCYTOSINE [J].

PANKIEWICZ, K ;

MATSUDA, A ;

WATANABE, KA .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (03) :485-488

[23] THE 2'-HYDROXYL FUNCTION ASSISTED CLEAVAGE OF THE INTERNUCLEOTIDE PHOSPHOTRIESTER BOND OF A RIBONUCLEOTIDE UNDER ACIDIC CONDITIONS [J].

PATHAK, T ;

CHATTOPADHYAYA, J .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1985, 39 (10) :799-806

[24]

PFISTER M, 1986, THESIS U KONSTANZ

[25] USE OF THE 1-(2-FLUOROPHENYL)-4-METHOXYPIPERIDIN-4-YL (FPMP) PROTECTING GROUP IN THE SOLID-PHASE SYNTHESIS OF OLIGORIBONUCLEOTIDES AND POLYRIBONUCLEOTIDES [J].

RAO, MV ;

REESE, CB ;

SCHEHLMANN, V ;

YU, PS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (01) :43-55

[26] SOLID-PHASE SYNTHESIS OF THE 3'-TERMINAL NONADECARIBONUCLEOSIDE OCTADECAPHOSPHATE SEQUENCE OF YEAST ALANINE TRANSFER-RIBONUCLEIC-ACID [J].

RAO, TS ;

REESE, CB ;

SERAFINOWSKA, HT ;

TAKAKU, H ;

ZAPPIA, G .

TETRAHEDRON LETTERS, 1987, 28 (41) :4897-4900

[27] 4-METHOXYTETRAHYDROPYRAN-4-UL - A SYMMETRICAL ALTERNATIVE TO TETRAHYDROPYRANYL PROTECTING GROUP [J].

REESE, CB ;

SAFFHILL, R ;

SULSTON, JE .

TETRAHEDRON, 1970, 26 (04) :1023-&

[28] STUDIES IN THE SOLID-PHASE SYNTHESIS OF OLIGO-RIBONUCLEOTIDES AND POLY-RIBONUCLEOTIDES [J].

REESE, CB ;

RAO, MV ;

SERAFINOWSKA, HT ;

THOMPSON, EA ;

YU, PS .

NUCLEOSIDES & NUCLEOTIDES, 1991, 10 (1-3) :81-97

[29] THE PROBLEM OF 2'-PROTECTION IN RAPID OLIGORIBONUCLEOTIDE SYNTHESIS [J].

REESE, CB .

NUCLEOSIDES & NUCLEOTIDES, 1987, 6 (1-2) :121-129

[30] ACTION OF ACID ON OLIGORIBONUCLEOTIDE PHOSPHOTRIESTER INTERMEDIATES - EFFECT OF RELEASED VICINAL HYDROXY FUNCTIONS [J].

REESE, CB ;

SKONE, PA .

NUCLEIC ACIDS RESEARCH, 1985, 13 (14) :5215-5231

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