ONE-POT SELECTIVE DEUTERIATION OF 5'-DIMETHOXYTRITYLATED DEOXYNUCLEOTIDE DERIVATIVES

被引:3
作者
CHEN, ST
CHEN, SY
CHOU, SH
CHEN, CR
HUANG, WC
WANG, KT
机构
[1] ACAD SINICA,INST BIOL CHEM,POB 23-106,TAIPEI 10098,TAIWAN
[2] NATL TAIWAN NORMAL UNIV,DEPT CHEM,TAIPEI 117,TAIWAN
[3] NATL TAIWAN UNIV,DEPT CHEM,TAIPEI,TAIWAN
[4] UNIV WASHINGTON,HOWARD HUGHES MED INST SL-15,SEATTLE,WA 98195
关键词
D O I
10.1016/S0960-894X(01)80849-0
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Procedures have been developed for selective incorporation of deuterium at C-6 of 5'-DMT-dC(Bz)@, C-8 of 5'-DMT-dA(Bz), C-8 of 5'-DMT-dG(i-Bu), and C-6 of 5'-DMT-dT in dimethylsulfoxide solution catalyzed by various amounts of base at 90-135-degrees-C with quantitative or nearly quantitative deuterium-labeling yields. The reactions of deuterium exchange of C-6 of 5'-DMT-dC(Bz), C-8 of 5'-DMT-dA(Bz), and C-8 of 5'-DMT-dG(i-Bu) were performed in a one-pot reaction procedure and that of C-6 of 5'-DMT-dT was achieved by deuteriation of 5'-unprotected dT, followed by dimethoxytritylation of 5'-OH with 4,4'-dimethoxytrityl chloride.
引用
收藏
页码:789 / 794
页数:6
相关论文
共 29 条
[1]  
ABOULELA F, 1988, NUCLEIC ACIDS RES, V16, P3559
[2]   DETERMINATION OF BIOMOLECULAR STRUCTURES FROM PROTON-PROTON NOES USING A RELAXATION MATRIX APPROACH [J].
BOELENS, R ;
KONING, TMG ;
KAPTEIN, R .
JOURNAL OF MOLECULAR STRUCTURE, 1988, 173 :299-311
[3]   2-DIMENSIONAL H-1-NMR STUDIES OF 32-BASE-PAIR SYNTHETIC IMMOBILE HOLLIDAY JUNCTIONS - COMPLETE ASSIGNMENTS OF THE LABILE PROTONS AND IDENTIFICATION OF THE BASE-PAIRING SCHEME [J].
CHEN, SM ;
HEFFRON, F ;
CHAZIN, WJ .
BIOCHEMISTRY, 1993, 32 (01) :319-326
[4]   SOLUTION STRUCTURE OF [D(GCGTATACGC)]2 [J].
CHENG, JW ;
CHOU, SH ;
SALAZAR, M ;
REID, BR .
JOURNAL OF MOLECULAR BIOLOGY, 1992, 228 (01) :118-137
[5]   ADJACENT G-A MISMATCH BASE-PAIRS CONTAIN B(II) PHOSPHODIESTERS IN SOLUTION [J].
CHOU, SH ;
CHENG, JW ;
FEDOROFF, OY ;
CHUPRINA, VP ;
REID, BR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :3114-3115
[6]   SOLUTION STRUCTURE OF [D(ATGAGCGAATA)]2 - ADJACENT G-A MISMATCHES STABILIZED BY CROSS-STRAND BASE-STACKING AND B(II) PHOSPHATE GROUPS [J].
CHOU, SH ;
CHENG, JW ;
REID, BR .
JOURNAL OF MOLECULAR BIOLOGY, 1992, 228 (01) :138-155
[7]   CRYSTAL AND SOLUTION STRUCTURES OF THE OLIGONUCLEOTIDE D(ATGCGCAT)2 - A COMBINED X-RAY AND NMR-STUDY [J].
CLARK, GR ;
BROWN, DG ;
SANDERSON, MR ;
CHWALINSKI, T ;
NEIDLE, S ;
VEAL, JM ;
JONES, RL ;
WILSON, WD ;
ZON, G ;
GARMAN, E ;
STUART, DI .
NUCLEIC ACIDS RESEARCH, 1990, 18 (18) :5521-5528
[8]   THE EFFECT OF CRYSTAL PACKING ON OLIGONUCLEOTIDE DOUBLE HELIX STRUCTURE [J].
DICKERSON, RE ;
GOODSELL, DS ;
KOPKA, ML ;
PJURA, PE .
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 1987, 5 (03) :557-579
[9]   CRYSTAL-LATTICE PACKING IS IMPORTANT IN DETERMINING THE BEND OF A DNA DODECAMER CONTAINING AN ADENINE TRACT [J].
DIGABRIELE, AD ;
SANDERSON, MR ;
STEITZ, TA .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (06) :1816-1820
[10]   A TETRAMERIC DNA-STRUCTURE WITH PROTONATED CYTOSINE.CYTOSINE BASE-PAIRS [J].
GEHRING, K ;
LEROY, JL ;
GUERON, M .
NATURE, 1993, 363 (6429) :561-565