Kinetics for the acid-catalyzed hydrolysis of purine and cytosine 2′-deoxy-4′-thionucleosides

被引:15
作者
Elzagheid, MI
Oivanen, M [1 ]
Walker, RT
Secrist, JA
机构
[1] Univ Turku, Dept Chem, FIN-20014 Turku, Finland
[2] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England
[3] So Res Inst, Birmingham, AL 35255 USA
来源
NUCLEOSIDES & NUCLEOTIDES | 1999年 / 18卷 / 02期
关键词
D O I
10.1080/15257779908043065
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
Hydrolysis of adenine, guanine and cytosine 2'-deoxy-4'-thionucleosides in aqueous acid has been followed by HPLC. Stability of the compounds and mechanisms of hydrolysis are discussed in comparison with those of the corresponding native 2'-deoxynucleosides.
引用
收藏
页码:181 / 186
页数:6
相关论文
共 21 条
[1]   Reactions of charged substrates .7. The methoxymethyl carbenium ion problem .2. A semiempirical study of the kinetic and thermodynamic stabilities of linear and cyclic oxo- and thiocarbenium ions generated from aldehyde hydrates, hemiacetals, acetals, and methyl ribosides and glucosides [J].
Buckley, N ;
Oppenheimer, NJ .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8048-8062
[2]   NUCLEIC-ACID HYDROLYSIS .1. ISOMERIZATION AND ANOMERIZATION OF PYRIMIDIC DEOXYRIBONUCLEOSIDES IN AN ACIDIC MEDIUM [J].
CADET, J ;
TEOULE, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (20) :6517-6519
[3]   THE SYNTHESIS AND ANTIVIRAL ACTIVITY OF SOME 4'-THIO-2'-DEOXY NUCLEOSIDE ANALOGS [J].
DYSON, MR ;
COE, PL ;
WALKER, RT .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) :2782-2786
[4]  
GARRETT ER, 1972, J AM CHEM SOC, V94, P8532, DOI 10.1021/ja00779a040
[5]   Some reactions of 4'-thionucleosides and their sulfones [J].
Hancox, EL ;
Walker, RT .
NUCLEOSIDES & NUCLEOTIDES, 1996, 15 (1-3) :135-148
[6]   Investigation of some properties of oligodeoxynucleotides containing 4'-thio-2'-deoxynucleotides: Duplex hybridization and nuclease sensitivity [J].
Jones, GD ;
Lesnik, EA ;
Owens, SR ;
Risen, LM ;
Walker, RT .
NUCLEIC ACIDS RESEARCH, 1996, 24 (21) :4117-4122
[7]   KINETICS AND MECHANISMS OF HYDROLYTIC REACTIONS OF METHYLATED CYTIDINES UNDER ACIDIC AND NEUTRAL CONDITIONS [J].
KUSMIEREK, J ;
KAPPI, R ;
NEUVONEN, K ;
SHUGAR, D ;
LONNBERG, H .
ACTA CHEMICA SCANDINAVICA, 1989, 43 (02) :196-202
[8]   MECHANISMS FOR THE SOLVOLYTIC DECOMPOSITIONS OF NUCLEOSIDE ANALOGS .4. THE EFFECT OF METAL-IONS ON THE ACIDIC HYDROLYSIS OF 9-(1-ETHOXYETHYL)PURINE [J].
LONNBERG, H .
ACTA CHEMICA SCANDINAVICA SERIES A-PHYSICAL AND INORGANIC CHEMISTRY, 1980, 34 (10) :703-708
[10]   ADDITIONAL EVIDENCE FOR THE EXCEPTIONAL MECHANISM OF THE ACID-CATALYZED HYDROLYSIS OF 4-OXOPYRIMIDINE NUCLEOSIDES - HYDROLYSIS OF 1-(1-ALKOXYALKYL)URACILS, SECONUCLEOSIDES, 3'-C-ALKYL NUCLEOSIDES AND NUCLEOSIDE 3',5'-CYCLIC MONOPHOSPHATES [J].
OIVANEN, M ;
RAJAMAKI, M ;
VARILA, J ;
HOVINEN, J ;
MIKHAILOV, S ;
LONNBERG, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (02) :309-314