A structural analog of the protosterol cation is not a strong inhibitor of sterol biosynthesis

被引:18
作者
Corey, EJ
Daley, DC
Cheng, HM
机构
[1] Department of Chemistry, Harvard University, Cambridge
关键词
D O I
10.1016/0040-4039(96)00577-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The relatively modest potency of inhibition of lanosterol synthase by the tetracyclic ammonium ion 10, a structural analog of the protosterol cation 4, IC50 = 22 mu M, indicates that the protosterol cation is not strongly bound by the enzyme. (C) 1996 Elsevier Science Ltd.
引用
收藏
页码:3287 / 3290
页数:4
相关论文
共 13 条
[1]   ENZYMATIC CYCLIZATION OF SQUALENE AND OXIDOSQUALENE TO STEROLS AND TRITERPENES [J].
ABE, I ;
ROHMER, M ;
PRESTWICH, GD .
CHEMICAL REVIEWS, 1993, 93 (06) :2189-2206
[2]   THE SQUALENE-2,3-EPOXIDE CYCLASE AS A MODEL FOR THE DEVELOPMENT OF NEW DRUGS [J].
CATTEL, L ;
CERUTI, M ;
VIOLA, F ;
DELPRINO, L ;
BALLIANO, G ;
DURIATTI, A ;
BOUVIERNAVE, P .
LIPIDS, 1986, 21 (01) :31-38
[3]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 19-AZASQUALENE 2,3-EPOXIDE AS INHIBITOR OF 2,3-OXIDOSQUALENE CYCLASE [J].
CERUTI, M ;
ROCCO, F ;
VIOLA, F ;
BALLIANO, G ;
GROSA, G ;
DOSIO, F ;
CATTEL, L .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (09) :675-682
[4]   2,3-IMINOSQUALENE A POTENT INHIBITOR OF ENZYMIC CYCLIZATION OF 2,3-OXIDOSQUALENE TO STEROLS [J].
COREY, EJ ;
DEMONTEL.PR ;
LIN, K ;
DEAN, PDG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (11) :2797-&
[5]   MOLECULAR-CLONING, CHARACTERIZATION, AND OVEREXPRESSION OF ERG7 THE SACCHAROMYCES-CEREVISIAE GENE ENCODING LANOSTEROL SYNTHASE [J].
COREY, EJ ;
MATSUDA, SPT ;
BARTEL, B .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (06) :2211-2215
[6]   AN EXPERIMENTAL DEMONSTRATION OF THE STEREOCHEMISTRY OF ENZYMATIC CYCLIZATION OF 2,3-OXIDOSQUALENE TO THE PROTOSTEROL SYSTEM, FORERUNNER OF LANOSTEROL AND CHOLESTEROL [J].
COREY, EJ ;
VIRGIL, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :4025-4026
[7]   ENANTIOSELECTIVE TOTAL SYNTHESIS OF A PROTOSTEROL, 3-BETA,20-DIHYDROXYPROTOST-24-ENE [J].
COREY, EJ ;
VIRGIL, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6429-6431
[8]   NEW INSIGHTS REGARDING THE CYCLIZATION PATHWAY FOR STEROL BIOSYNTHESIS FROM (S)-2,3-OXIDOSQUALENE [J].
COREY, EJ ;
VIRGIL, SC ;
CHENG, HM ;
BAKER, CH ;
MATSUDA, SPT ;
SINGH, V ;
SARSHAR, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (47) :11819-11820
[9]   NEW MECHANISTIC AND STEREOCHEMICAL INSIGHTS ON THE BIOSYNTHESIS OF STEROLS FROM 2,3-OXIDOSQUALENE [J].
COREY, EJ ;
VIRGIL, SC ;
SARSHAR, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8171-8172
[10]  
COREY EJ, 1996, TETRAHEDRON LETT, V37