The synthesis of deuterionucleosides

被引:19
作者
Földesi, A [1 ]
Trifonova, A [1 ]
Kundu, MK [1 ]
Chattopadhyaya, J [1 ]
机构
[1] Uppsala Univ, Ctr Biomed, Dept Bioorgan Chem, S-75123 Uppsala, Sweden
关键词
D O I
10.1080/15257770008045450
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
The synthesis of deuterionucleosides for site-specific incorporation into oligo-DNA or -RNA is herein reviewed for NMR or biological studies. The review covers the following aspects: (i) deuteration of the aglycone; (ii) single-site chemical deuteration of the sugar residues; (iii) multiple-site chemical deuteration of the sugar residues; (iv) enzymatic synthesis of deuterated nucleosides or nucleotides; and (v) synthesis of labelled nucleosides with multiple isotopes.
引用
收藏
页码:1615 / 1656
页数:42
相关论文
共 243 条
[81]   A SOLID-STATE DEUTERIUM NMR-STUDY OF FURANOSE RING DYNAMICS IN [D(CGCGAATTCGCG)]2 [J].
HUANG, WC ;
ORBAN, J ;
KINTANAR, A ;
REID, BR ;
DROBNY, GP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) :9059-9068
[82]   An efficient and economic site-specific deuteration strategy for NMR studies of homologous oligonucleotide repeat sequences [J].
Huang, XN ;
Yu, PL ;
LeProust, E ;
Gao, XL .
NUCLEIC ACIDS RESEARCH, 1997, 25 (23) :4758-4763
[83]   BROMINATION OF ADENINE NUCLEOSIDE AND NUCLEOTIDE [J].
IKEHARA, M ;
UESUGI, S ;
KANEKO, M .
CHEMICAL COMMUNICATIONS, 1967, (01) :17-&
[84]  
Jung ME, 1998, HETEROCYCLES, V47, P349
[85]   BISULFITE-CATALYZED ISOTOPE LABELING OF CYTIDINE 5'-PHOSPHATE AT ITS 5 POSITION [J].
KAI, K ;
WATAYA, Y ;
HAYATSU, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (08) :2089-&
[87]   SONOCHEMICAL AND TRIETHYLBORANE-INDUCED TIN DEUTERIDE REDUCTION FOR THE HIGHLY STEREOSELECTIVE SYNTHESIS OF (2'R)-[2'-H-2]-2'-DEOXYRIBONUCLEOSIDES FROM 2'-FUNCTIONALIZED RIBONUCLEOSIDES [J].
KAWASHIMA, E ;
AOYAMA, Y ;
SEKINE, T ;
NAKAMURA, E ;
KAINOSHO, M ;
KYOGOKU, Y ;
ISHIDO, Y .
TETRAHEDRON LETTERS, 1993, 34 (08) :1317-1320
[88]   Tris(trimethylsilyl)[H-2]silane-triethylborane system producing the highly diastereoselective deuteration (> 99:1) of 2'-bromo-2'-deoxy- and 2'-O-phenoxythiocarbonylribonucleosides at 0 degrees C [J].
Kawashima, E ;
Uchida, S ;
Miyahara, M ;
Ishido, Y .
TETRAHEDRON LETTERS, 1997, 38 (42) :7369-7372
[89]   HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF (2'S)-[2'-H-2]-2'-DEOXYRIBONUCLEOSIDES FROM THE CORRESPONDING RIBONUCLEOSIDES [J].
KAWASHIMA, E ;
AOYAMA, Y ;
RADWAN, MF ;
MIYAHARA, M ;
SEKINE, T ;
KAINOSHO, M ;
KYOGOKU, Y ;
ISHIDO, Y .
NUCLEOSIDES & NUCLEOTIDES, 1995, 14 (3-5) :333-336
[90]   SONOCHEMICAL AND TRIETHYLBORANE-INDUCED TIN DEUTERIDE REDUCTION FOR THE HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF (2'R)-2'-DEOXY[2'-H-2]RIBONUCLEOSIDE DERIVATIVES [J].
KAWASHIMA, E ;
AOYAMA, Y ;
SEKINE, T ;
MIYAHARA, M ;
RADWAN, MF ;
NAKAMURA, E ;
KAINOSHO, M ;
KYOGOKU, Y ;
ISHIDO, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6980-6986