The action of adenosine deaminase (EC 3.5.4.4.) on adenosine and deoxyadenosine acetates:: The crucial role of the 5′-hydroxy group for the enzyme activity

被引：25
作者：
Ciuffreda, P [1 ]
Casati, S [1 ]
Santaniello, E [1 ]
机构：
[1] Univ Milan, LITA Vialba, Dipartimento Sci Preclin, I-20157 Milan, Italy
来源：
TETRAHEDRON | 2000年 / 56卷 / 20期
关键词：
deamination; enzymes and enzyme reactions; nucleosides;
D O I：
10.1016/S0040-4020(00)00222-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
From adenosine 1,2'-deoxyadenosine 3 and 3'-deoxyadenosine 5 all the acetates were prepared by lipase-catalyzed reactions. Only the acetates with free 5'-hydroxy group were deaminated by adenosine deaminase (ADA), confirming the crucial role of 5'-OH for the enzyme activity. (C) 2000 Elsevier Science Ltd. All rights reserved.
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收藏
页码：3239 / 3243
页数：5
相关论文
共 22 条
  • [1] ANDERSEN A, 1954, J CHEM SOC, P1882
  • [2] BREDERECK H, 1940, CHEM BER, V73, P269
  • [3] Lipase-catalyzed protection of the hydroxy groups of the nucleosides inosine and 2′-deoxyinosine:: A new chemoenzymatic synthesis of the antiviral drug 2′,3′-dideoxyinosine
    Ciuffreda, P
    Casati, S
    Santaniello, E
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (11) : 1577 - 1582
  • [4] STRUCTURAL REQUIREMENTS OF NUCLEOSIDES FOR BINDING BY ADENOSINE DEAMINASE
    CORY, JG
    SUHADOLNIK, RJ
    [J]. BIOCHEMISTRY, 1965, 4 (09) : 1729 - +
  • [5] DECHLORONASE ACTIVITY OF ADENOSINE DEAMINASE
    CORY, JG
    SUHADOLNIK, RJ
    [J]. BIOCHEMISTRY, 1965, 4 (09) : 1733 - +
  • [6] ENZYMATIC-REACTIONS IN ORGANIC-SYNTHESIS .2. ESTER INTERCHANGE OF VINYL ESTERS
    DEGUEILCASTAING, M
    DEJESO, B
    DROUILLARD, S
    MAILLARD, B
    [J]. TETRAHEDRON LETTERS, 1987, 28 (09) : 953 - 954
  • [7] LIPOPHILIC, ACID-STABLE, ADENOSINE DEAMINASE-ACTIVATED ANTI-HIV PRODRUGS FOR CENTRAL-NERVOUS-SYSTEM DELIVERY .2. 6-HALO AND 6-ALKOXY PRODRUGS OF 2'-BETA-FLUORO-2',3'-DIDEOXYINOSINE
    FORD, H
    SIDDIQUI, MA
    DRISCOLL, JS
    MARQUEZ, VE
    KELLEY, JA
    MITSUYA, H
    SHIRASAKA, T
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (07) : 1189 - 1195
  • [8] PARTIAL PROTECTION OF CARBOHYDRATE-DERIVATIVES .3. REGIOSELECTIVE 2'-O-DEACYLATION OF FULLY ACYLATED PURINE AND PYRIMIDINE RIBONUCLEOSIDES WITH HYDRAZINE HYDRATE
    ISHIDO, Y
    NAKAZAKI, N
    SAKAIRI, N
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (08): : 2088 - 2098
  • [9] A NUCLEOSIDE DERIVATIVE FROM EMERICELLA-NIDULANS
    KAWAHARA, N
    SEKITA, S
    SATAKE, M
    UDAGAWA, S
    [J]. PHYTOCHEMISTRY, 1992, 31 (04) : 1409 - 1410
  • [10] Levene PA, 1937, J BIOL CHEM, V121, P131
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