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
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.
引用
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 [J].
Ciuffreda, P ;
Casati, S ;
Santaniello, E .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (11) :1577-1582
[4]   STRUCTURAL REQUIREMENTS OF NUCLEOSIDES FOR BINDING BY ADENOSINE DEAMINASE [J].
CORY, JG ;
SUHADOLNIK, RJ .
BIOCHEMISTRY, 1965, 4 (09) :1729-+
[5]   DECHLORONASE ACTIVITY OF ADENOSINE DEAMINASE [J].
CORY, JG ;
SUHADOLNIK, RJ .
BIOCHEMISTRY, 1965, 4 (09) :1733-+
[6]   ENZYMATIC-REACTIONS IN ORGANIC-SYNTHESIS .2. ESTER INTERCHANGE OF VINYL ESTERS [J].
DEGUEILCASTAING, M ;
DEJESO, B ;
DROUILLARD, S ;
MAILLARD, B .
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 [J].
FORD, H ;
SIDDIQUI, MA ;
DRISCOLL, JS ;
MARQUEZ, VE ;
KELLEY, JA ;
MITSUYA, H ;
SHIRASAKA, T .
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 [J].
ISHIDO, Y ;
NAKAZAKI, N ;
SAKAIRI, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (08) :2088-2098
[9]   A NUCLEOSIDE DERIVATIVE FROM EMERICELLA-NIDULANS [J].
KAWAHARA, N ;
SEKITA, S ;
SATAKE, M ;
UDAGAWA, S .
PHYTOCHEMISTRY, 1992, 31 (04) :1409-1410
[10]  
Levene PA, 1937, J BIOL CHEM, V121, P131