Synthesis of nucleosides and related compounds .38. Deamination of 9-(hydroxymethylated cycloalkyl)-9H-adenines (carbocyclic adenine nucleosides) by adenosine deaminase: Effect of high-pressure upon deamination rate and enantioselectivity

被引:23
作者
Katagiri, N [1 ]
Ito, Y [1 ]
Shiraishi, T [1 ]
Maruyama, T [1 ]
Sato, Y [1 ]
Kaneko, C [1 ]
机构
[1] TOKUSHIMA BUNRI UNIV,FAC PHARMACEUT SCI,YAMASHIRO,TOKUSHIMA 770,JAPAN
来源
NUCLEOSIDES & NUCLEOTIDES | 1996年 / 15卷 / 1-3期
关键词
D O I
10.1080/07328319608002411
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
The deamination of eight kinds of racemic carbocyclic adenine nucleosides by adenosine deaminase under high-pressure (400 MPa) was examined and the result was compared with that obtained from the reaction under atmospheric pressure. The deamination of all carbocyclic nucleosides irrespective to their ring size of carbocycles was facilitated remarkably by high-pressure. The reaction of three and five membered carbocyclic pressure whereas the enantioselectivity of six membered carbocyclic nucleosides was suppressed under high-pressure. However, the enantioselectivity of four membered nucleosides was low under both conditions.
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页码:631 / 647
页数:17
相关论文
共 19 条
[11]  
MALPASS JR, 1976, J CHEMS OC P1, P874
[12]   BIOCHEMISTRY OF DISEASES OF IMMUNODEVELOPMENT [J].
MARTIN, DW ;
GELFAND, EW .
ANNUAL REVIEW OF BIOCHEMISTRY, 1981, 50 :845-877
[13]  
NORBECK DW, 1990, Patent No. 0366059
[14]   DERIVATIVES OF OXETANOCIN - OXETANOCIN-H, OXETANOCIN-X AND OXETANOCIN-G, AND 2-AMINOOXETANOCIN-A [J].
SHIMADA, N ;
HASEGAWA, S ;
SAITO, S ;
NISHIKIORI, T ;
FUJII, A ;
TAKITA, T .
JOURNAL OF ANTIBIOTICS, 1987, 40 (12) :1788-1790
[15]   SYNTHESIS OF SQ-33,054, A NOVEL CYCLOBUTANE NUCLEOSIDE WITH POTENT ANTIVIRAL ACTIVITY [J].
SLUSARCHYK, WA ;
YOUNG, MG ;
BISACCHI, GS ;
HOCKSTEIN, DR ;
ZAHLER, R .
TETRAHEDRON LETTERS, 1989, 30 (47) :6453-6456
[16]   ADDITION OF MOLECULAR FLUORINE TO BICYCLO[2.2.1]HEPT-2-ENE DERIVATIVES AND CONVERSION TO FLUORINE-CONTAINING CARBOCYCLIC NUCLEOSIDES [J].
TOYOTA, A ;
HABUTANI, C ;
KATAGIRI, N ;
KANEKO, C .
TETRAHEDRON LETTERS, 1994, 35 (31) :5665-5668
[17]   RESOLUTION OF RACEMIC CARBOVIR AND SELECTIVE-INHIBITION OF HUMAN-IMMUNODEFICIENCY-VIRUS BY THE (-) ENANTIOMER [J].
VINCE, R ;
BROWNELL, J .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 168 (03) :912-916
[18]   POTENT AND SELECTIVE ACTIVITY OF A NEW CARBOCYCLIC NUCLEOSIDE ANALOG (CARBOVIR-NSC-614846) AGAINST HUMAN IMMUNODEFICIENCY VIRUS INVITRO [J].
VINCE, R ;
HUA, M ;
BROWNELL, J ;
DALUGE, S ;
LEE, FC ;
SHANNON, WM ;
LAVELLE, GC ;
QUALLS, J ;
WEISLOW, OS ;
KISER, R ;
CANONICO, PG ;
SCHULTZ, RH ;
NARAYANAN, VL ;
MAYO, JG ;
SHOEMAKER, RH ;
BOYD, MR .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1988, 156 (02) :1046-1053
[19]   ATOMIC-STRUCTURE OF ADENOSINE-DEAMINASE COMPLEXED WITH A TRANSITION-STATE ANALOG - UNDERSTANDING CATALYSIS AND IMMUNODEFICIENCY MUTATIONS [J].
WILSON, DK ;
RUDOLPH, FB ;
QUIOCHO, FA .
SCIENCE, 1991, 252 (5010) :1278-1284