THE PROOLIGONUCLEOTIDE APPROACH .1. ESTERASE-MEDIATED REVERSIBILITY OF DITHYMIDINE-S-ALKYL-PHOSPHOROTHIOLATES TO DITHYMIDINE PHOSPHOROTHIOATES

被引:45
作者
BARBER, I [1 ]
RAYNER, B [1 ]
IMBACH, JL [1 ]
机构
[1] UNIV MONTPELLIER 2,CHIM BIOORGAN LAB,CNRS,URA 488,F-34095 MONTPELLIER 5,FRANCE
关键词
D O I
10.1016/0960-894X(95)00074-4
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Alkylation of dithymidine phosphorothioate and phosphorodithioate with various iodoalkyl acylates afforded the corresponding uncharged S-alkyl phosphoromono- and di-thioates respectively. Upon incubation of these triesters in CEM cell extracts, the bioreversible alkyl acylate masking groups were selectively and rapidly removed by carboxyesterases present in the milieu, yielding the starting dinucleoside diesters.
引用
收藏
页码:563 / 568
页数:6
相关论文
共 19 条
  • [1] BELSNER K, 1982, SYNTHESIS-STUTTGART, P239
  • [2] BENZARIA S, 1994, NUCLEIC ACIDS S SERI, P129
  • [3] MECHANISMS OF NUCLEOPHILIC SUBSTITUTION IN PHOSPHATE ESTERS
    COX, JR
    RAMSAY, OB
    [J]. CHEMICAL REVIEWS, 1964, 64 (04) : 317 - &
  • [4] A CONVENIENT SYNTHESIS OF DIETHYL (MERCAPTOMETHYL)PHOSPHONATE
    FARRINGTON, GK
    KUMAR, A
    WEDLER, FC
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1989, 21 (03) : 390 - 392
  • [5] SITE-SPECIFIC LABELING OF DNA-SEQUENCES CONTAINING PHOSPHOROTHIOATE DIESTERS
    FIDANZA, JA
    OZAKI, H
    MCLAUGHLIN, LW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) : 5509 - 5517
  • [6] GILES RV, 1993, ANTI-CANCER DRUG DES, V8, P33
  • [7] DNA AND RNA SEQUENCE DETERMINATION BASED ON PHOSPHOROTHIOATE CHEMISTRY
    GISH, G
    ECKSTEIN, F
    [J]. SCIENCE, 1988, 240 (4858) : 1520 - 1522
  • [8] STEREOSPECIFIC BIO-REVERSIBILITY OF DINUCLEOSIDE S-ALKYL PHOSPHOROTHIOLATES TO DINUCLEOSIDE PHOSPHOROTHIOATES
    IYER, RP
    YU, D
    AGRAWAL, S
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (20) : 2471 - 2476
  • [9] MIYAKE A, 1985, Patent No. 143601
  • [10] RATIONAL DESIGN FOR CYTOSOLIC DELIVERY OF NUCLEOSIDE MONOPHOSPHATES - SATE AND DTE AS ENZYME-LABILE TRANSIENT PHOSPHATE PROTECTING GROUPS
    PERIGAUD, C
    GOSSELIN, G
    LEFEBVRE, I
    GIRARDET, JL
    BENZARIA, S
    BARBER, I
    IMBACH, JL
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (12) : 2521 - 2526