Systematic synthesis of specifically 13C/2H-labeled nucleosides from [ul-13C6]-D-Glucose

被引：19

作者：

Ono, A ^{[1
]}

Shiina, T ^{[1
]}

Ono, A ^{[1
]}

Kainosho, M ^{[1
]}

机构：

[1] Tokyo Metropolitan Univ, Fac Sci, Dept Chem, Tokyo 1920397, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(98)00432-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A systematic approach, which combines previously reported reactions with appropriate modifications, was established for preparing a variety of selectively deuterated nucleosides from glucose. We have developed a systematic method of synthesizing specifically deuterated nucleosides from glucose. Selectively C-13/H-2-doubly labeled nucleosides, such as [1',2',3',4',5'-C-13(5);3',5'-H-2(2)]- and [1',2',3',4',5'-C-13(5);4',5'-H-2(2)]-adenosines, have been synthesized starting from [ul-C-13(6)]-D-glucose. These labeled nucleosides are very useful for precise conformational analyses of nucleic acids in solution by heteronuclear multidimensional NMR spectroscopy. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2793 / 2796

页数：4

共 29 条

[21] C-13 CHEMICAL-SHIFTS OF FURANOSIDES AND CYCLOPENTANOLS - CONFIGURATIONAL AND CONFORMATIONAL INFLUENCES [J].

RITCHIE, RGS ;

CYR, N ;

KORSCH, B ;

KOCH, HJ ;

PERLIN, AS .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (10) :1424-1433

[22] MECHANISM OF ACTION OF S-ADENOSYL-L-HOMOCYSTEINE HYDROLASE - MEASUREMENT OF KINETIC ISOTOPE EFFECTS USING ADENOSINE-3'-D AND S-ADENOSYL-L-HOMOCYSTEINE-3'-D AS SUBSTRATES [J].

SINHABABU, AK ;

BARTEL, RL ;

POCHOPIN, N ;

BORCHARDT, RT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) :7628-7632

[23] AN ALTERNATIVE TRIPLE-RESONANCE METHOD FOR THE THROUGH-BOND CORRELATION OF INTRANUCLEOTIDE H1' AND H8 NMR SIGNALS OF PURINE NUCLEOTIDES - APPLICATION TO A DNA DODECAMER WITH FULLY C-13/N-15-LABELED DEOXYADENOSINE RESIDUES [J].

TATE, S ;

ONO, A ;

KAINOSHO, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5977-5978

[24] SEQUENTIAL BACKBONE ASSIGNMENT IN C-13-LABELED DNA BY THE H-1, C-13, P-31 TRIPLE-RESONANCE EXPERIMENT, HCP-CCH-COSY [J].

TATE, S ;

ONO, A ;

KAINOSHO, M .

JOURNAL OF MAGNETIC RESONANCE SERIES B, 1995, 106 (01) :89-91

[25] STEREOSPECIFIC MEASUREMENTS OF THE VICINAL H-1-P-31 COUPLING-CONSTANTS FOR THE DIASTEREOTOPIC C5' METHYLENE PROTONS IN A DNA DODECAMER WITH A C-13/H-2 DOUBLY LABELED RESIDUE - CONFORMATIONAL-ANALYSIS OF THE TORSION ANGLE-BETA [J].

TATE, S ;

KUBO, Y ;

ONO, A ;

KAINOSHO, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (27) :7277-7278

[26] Preparation of specifically deuterated RNA for NMR studies using a combination of chemical and enzymatic synthesis [J].

Tolbert, TJ ;

Williamson, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (34) :7929-7940

[27] NUCLEOSIDE SYNTHESES .22. NUCLEOSIDE SYNTHESIS WITH TRIMETHYLSILYL TRIFLATE AND PERCHLORATE AS CATALYSTS [J].

VORBRUGGEN, H ;

KROLIKIEWICZ, K ;

BENNUA, B .

CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (04) :1234-1255

[28] NMR OF ENZYMATICALLY SYNTHESIZED UNIFORMLY (CN)-C-13-N-15-LABELED DNA OLIGONUCLEOTIDES [J].

ZIMMER, DP ;

CROTHERS, DM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (08) :3091-3095

[29]

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