Synthesis of RNA using 2′-O-DTM protection

被引:64
作者
Semenyuk, Andrey
Foldesi, Andras
Johansson, Tommy
Estmer-Nilsson, Camilla
Blomgren, Peter
Brannvall, Mathias
Kirsebom, Leif A.
Kwiatkowski, Marek [1 ]
机构
[1] Uppsala Univ, Dept Genet & Pathol, Uppsala, Sweden
[2] Quiatech AB, Uppsala, Sweden
[3] Uppsala Univ, BMC, Dept Cell & Mol Biol, Uppsala, Sweden
关键词
D O I
10.1021/ja0636587
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
tert-Butyldithiomethyl (DTM), a novel hydroxyl protecting group, cleavable under reductive conditions, was developed and applied for the protection of 2′-OH during solid-phase RNA synthesis. This function is compatible with all standard protecting groups used in oligonucleotide synthesis, and allows for fast and high-yield synthesis of RNA. Oligonucleotides containing the 2′-O-DTM groups can be easily deprotected under the mildest possible aqueous and homogeneous conditions. The preserved 5′-O-DMTr function can be used for high-throughput cartridge RNA purification. Copyright © 2006 American Chemical Society.
引用
收藏
页码:12356 / 12357
页数:2
相关论文
共 16 条
[1]   RIBONUCLEOSIDE ANALYSIS BY REVERSED-PHASE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].
GEHRKE, CW ;
KUO, KC .
JOURNAL OF CHROMATOGRAPHY, 1989, 471 :3-36
[2]   Design, synthesis, and analysis of yeast tRNA(Phe) analogs possessing intra- and interhelical disulfide cross-links [J].
Goodwin, JT ;
Osborne, SE ;
Scholle, EJ ;
Glick, GD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (22) :5207-5215
[3]   DIPHENYLCARBAMOYL AND PROPIONYL GROUPS - A NEW COMBINATION OF PROTECTING GROUPS FOR THE GUANINE RESIDUE [J].
KAMIMURA, T ;
TSUCHIYA, M ;
KOURA, K ;
SEKINE, M ;
HATA, T .
TETRAHEDRON LETTERS, 1983, 24 (27) :2775-2778
[4]   The P15-loop of Escherichia coli RNase P RNA is an autonomous divalent metal ion binding domain [J].
Kufel, J ;
Kirsebom, LA .
RNA, 1998, 4 (07) :777-788
[5]   A new RNA synthetic method with a 2′-O-(2-cyanoethoxymethyl) protecting group [J].
Ohgi, T ;
Masutomi, Y ;
Ishiyama, K ;
Kitagawa, H ;
Shiba, Y ;
Yano, J .
ORGANIC LETTERS, 2005, 7 (16) :3477-3480
[6]   Improved synthesis of oligonucleotides containing 2-thiouridine derivatives by use of diluted iodine solution [J].
Okamoto, I ;
Seio, K ;
Sekine, M .
TETRAHEDRON LETTERS, 2006, 47 (04) :583-585
[7]  
Pitsch S, 2001, HELV CHIM ACTA, V84, P3773, DOI 10.1002/1522-2675(20011219)84:12<3773::AID-HLCA3773>3.0.CO
[8]  
2-E
[9]   Spontaneous aminoacylation of a RNA sequence containing a 3′-terminal-2′-thioadenosine [J].
Porcher, S ;
Meyyappan, M ;
Pitsch, S .
HELVETICA CHIMICA ACTA, 2005, 88 (11) :2897-2909
[10]   CHEMICAL SYNTHESIS OF A PENTARIBONUCLEOSIDE TETRAPHOSPHATE CONSTITUTING THE 3'-ACCEPTOR STEM SEQUENCE OF ESCHERICHIA-COLI TRANSFER RNAILE USING 2'-O-(3-METHOXY-1,5-DICARBOMETHOXYPENTAN-3-YL)-RIBONUCLEOSIDE BUILDING-BLOCKS - APPLICATION OF A NEW ACHIRAL AND ACID-LABILE 2'-HYDROXYL PROTECTING GROUP IN TRANSFER-RNA SYNTHESISM [J].
SANDSTROM, A ;
KWIATKOWSKI, M ;
CHATTOPADHYAYA, J .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1985, 39 (04) :273-290