SYNTHESIS AND CHARACTERIZATION OF OLIGODEOXYNUCLEOTIDES CONTAINING THE MUTAGENIC BASE ANALOG 4-O-ETHYLTHYMINE

被引:29
作者
FERNANDEZFORNER, D
PALOM, Y
IKUTA, S
PEDROSO, E
ERITJA, R
机构
[1] UNIV BARCELONA,DEPT ORGAN CHEM,MARTI & FRANQUES 1-11,E-08028 BARCELONA,SPAIN
[2] CTR RES & DEV,DEPT MOLEC GENET,E-08034 BARCELONA,SPAIN
[3] IIT,DEPT CHEM,CHICAGO,IL 60616
关键词
D O I
10.1093/nar/18.19.5729
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
A method for the preparation of oligonucleotides containing the mutagenic base 4-O-ethyHhymine is described for the first time. Use of p-nitrophenylethyl type base protecting groups together with phosphite-triester solid-phase methodology makes possible the rapid and efficient preparation of oligonucleotides bearing 4-O-ethylthymine, while standard base protecting groups are not compatible with the presence of this base. Possible applications of this methodology are discussed. © 1990 Oxford University Press.
引用
收藏
页码:5729 / 5734
页数:6
相关论文
共 18 条
[1]   A STUDY OF SIDE REACTIONS OCCURRING DURING SYNTHESIS OF OLIGODEOXYNUCLEOTIDES CONTAINING O6-ALKYLDEOXYGUANOSINE RESIDUES AT PRESELECTED SITES [J].
BOROWYBOROWSKI, H ;
CHAMBERS, RW .
BIOCHEMISTRY, 1987, 26 (09) :2465-2471
[2]   SOLID-PHASE SYNTHESIS AND SIDE REACTIONS OF OLIGONUCLEOTIDES CONTAINING O-ALKYLTHYMINE RESIDUES [J].
BOROWYBOROWSKI, H ;
CHAMBERS, RW .
BIOCHEMISTRY, 1989, 28 (04) :1471-1477
[3]   SYNTHESIS AND PROPERTIES OF OLIGONUCLEOTIDES CONTAINING 4-THIOTHYMIDINE, 5-METHYL-2-PYRIMIDINONE-1-BETA-D(2'-DEOXYRIBOSIDE) AND 2-THIOTHYMIDINE [J].
CONNOLLY, BA ;
NEWMAN, PC .
NUCLEIC ACIDS RESEARCH, 1989, 17 (13) :4957-4974
[4]   USE OF A DODECADEOXYNUCLEOTIDE TO STUDY REPAIR OF THE O-4-METHYLTHYMINE LESION [J].
DOLAN, ME ;
OPLINGER, M ;
PEGG, AE .
MUTATION RESEARCH, 1988, 193 (02) :131-137
[5]  
GAIT MJ, 1984, OLIGONUCLEOTIDE SYNT, P47
[6]   NUCLEOTIDES .31. MODIFIED OLIGOMERIC 2'-5' A ANALOGS - SYNTHESIS OF 2'-5' OLIGONUCLEOTIDES WITH 9-(3'-AZIDO-3'-DEOXY-BETA-D-XYLOFURANOSYL)ADENINE AND 9-(3'-AMINO-3'-DEOXY-BETA-D-XYLOFURANOSYL)ADENINE AS MODIFIED NUCLEOSIDES [J].
HERDEWIJN, P ;
CHARUBALA, R ;
PFLEIDERER, W .
HELVETICA CHIMICA ACTA, 1989, 72 (08) :1729-1738
[7]   THE PARA-NITROPHENYLETHYL (NPE) GROUP - A VERSATILE NEW BLOCKING GROUP FOR PHOSPHATE AND AGLYCONE PROTECTION IN NUCLEOSIDES AND NUCLEOTIDES [J].
HIMMELSBACH, F ;
SCHULZ, BS ;
TRICHTINGER, T ;
CHARUBALA, R ;
PFLEIDERER, W .
TETRAHEDRON, 1984, 40 (01) :59-72
[8]   SYNTHESIS AND CHARACTERIZATION OF OLIGODEOXYNUCLEOTIDES CONTAINING 4-O-METHYLTHYMINE [J].
LI, BFL ;
REESE, CB ;
SWANN, PF .
BIOCHEMISTRY, 1987, 26 (04) :1086-1093
[9]   APPLICATION OF 2-CYANOETHYL N,N,N',N'-TETRAISOPROPYLPHOSPHORODIAMIDITE FOR INSITU PREPARATION OF DEOXYRIBONUCLEOSIDE PHOSPHORAMIDITES AND THEIR USE IN POLYMER-SUPPORTED SYNTHESIS OF OLIGODEOXYRIBONUCLEOTIDES [J].
NIELSEN, J ;
TAAGAARD, M ;
MARUGG, JE ;
VANBOOM, JH ;
DAHL, O .
NUCLEIC ACIDS RESEARCH, 1986, 14 (18) :7391-7403
[10]  
Pegg A E, 1977, Adv Cancer Res, V25, P195, DOI 10.1016/S0065-230X(08)60635-1