ONE-FLASK SYNTHESES OF 6-THIOGUANOSINE AND 2'-DEOXY-6-THIOGUANOSINE

被引:30
|
作者
KUNG, PP [1 ]
JONES, RA [1 ]
机构
[1] RUTGERS STATE UNIV,DEPT CHEM,PISCATAWAY,NJ 08855
关键词
6-THIOGUANOSINE; 2'-DEOXY-6-THIOGUANOSINE; 2-AMINO-9-(2-DEOXY-BETA-D-ERYTHRO-PENTOFURANOSYL)PURINE;
D O I
10.1016/0040-4039(91)80589-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have previously reported that reaction of guanosine or 2'-deoxyguanosine with trifluoroacetic anhydride in pyridine gives a putative 6-pyridyl intermediate from which several 6-substituted derivatives may be obtained.1 We now report high-yield conversion of guanosine and 2'-deoxyguanosine to the corresponding 6-thio compounds in a two-step, one-flask reaction via this 6-pyridyl intermediate. Standard Raney nickel treatment, as reported for the ribonucleoside,2 then gives the 2-aminopurine nucleosides.
引用
收藏
页码:3919 / 3922
页数:4
相关论文
共 50 条
  • [1] STRUCTURE AND STABILITY OF AN OLIGONUCLEOTIDE CONTAINING 2'-DEOXY-6-THIOGUANOSINE
    CHRISTOPHERSON, MS
    BROOM, AD
    NUCLEOSIDES & NUCLEOTIDES, 1994, 13 (1-3): : 351 - 368
  • [2] CRYSTAL-STRUCTURE OF 2'-DEOXY-6-THIOGUANOSINE MONOHYDRATE
    GARTLAND, GL
    BUGG, CE
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1977, 33 (DEC): : 3678 - 3681
  • [3] STRUCTURE AND STABILITY OF AN OLIGONUCLEOTIDE CONTAINING 2'-DEOXY-6-THIOGUANOSINE
    CHRISTOPHERSON, MS
    BROOM, AD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 204 : 182 - MEDI
  • [4] INCORPORATION OF 6-THIOGUANOSINE INTO OLIGORIBONUCLEOTIDES
    ADAMS, CJ
    MURRAY, JB
    FARROW, MA
    ARNOLD, JRP
    STOCKLEY, PG
    TETRAHEDRON LETTERS, 1995, 36 (30) : 5421 - 5424
  • [5] SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING 2'-DEOXY-6-THIOGUANOSINE AT A PREDETERMINED SITE
    CHRISTOPHERSON, MS
    BROOM, AD
    NUCLEIC ACIDS RESEARCH, 1991, 19 (20) : 5719 - 5724
  • [6] Transglycosylation reaction of 6-thioguanosine
    Manikowski, A
    Boryski, J
    NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (11-12): : 2367 - 2377
  • [7] AN APPROACH TO THE SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING 2'-DEOXY-6-THIOGUANOSINE AT A PREDETERMINED SITE
    CHRISTOPHERSON, MS
    BROOM, AD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 100 - MEDI
  • [8] Conversion of 6-Thioguanosine Diphosphate to 6-Thioguanosine Triphosphate is Mediated by Nucleoside Diphosphate Kinase Isoform A and B
    Karner, Susanne
    Schaeffeler, Elke
    Hofmann, Ute
    Shi, Shaojun
    Klein, Kathrin
    Zanger, Ulrich M.
    Schwab, Matthias
    BASIC & CLINICAL PHARMACOLOGY & TOXICOLOGY, 2009, 104 (06) : 497 - 497
  • [9] A NEW ODORLESS PROCEDURE FOR THE SYNTHESIS OF 2′-DEOXY-6-THIOGUANOSINE AND ITS INCORPORATION INTO OLIGODEOXYNUCLEOTIDES
    Onizuka, Kazumitsu
    Taniguchi, Yosuke
    Sasaki, Shigeki
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2009, 28 (08): : 752 - 760
  • [10] Synthesis and crystal structure of a nickel(II) 2′-deoxy-6-thioguanosine nitrate complex
    Hribesh, Samira O.
    Clegg, William
    Harrington, Ross W.
    Houlton, Andrew
    Pike, Andrew R.
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2025, 81 : 165 - +