Theoretical evidence for a concerted mechanism of the oxirane cleavage and A-ring formation in oxidosqualene cyclization

被引：46

作者：

Gao, DQ

Pan, YK ^{[1
]}

Byun, K

Gao, JL

机构：

[1] Boston Coll, Dept Chem, Chestnut Hill, MA 02167 USA

[2] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1998年 / 120卷 / 16期

关键词：

D O I：

10.1021/ja973983h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

引用

页码：4045 / 4046

页数：2

共 25 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] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[3] Methodology for the preparation of pure recombinant S-cerevisiae lanosterol synthase using a Baculovirus expression system. Evidence that oxirane cleavage and A-ring formation are concerted in the biosynthesis of lanosterol from 2,3-oxidosqualene [J].

Corey, EJ ;

Cheng, HM ;

Baker, CH ;

Matsuda, SPT ;

Li, D ;

Song, XL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (06) :1277-1288

[4] Studies on the substrate binding segments and catalytic action of lanosterol synthase. Affinity labeling with carbocations derived from mechanism-based analogs of 2,3-oxidosqualene and site-directed mutagenesis probes [J].

Corey, EJ ;

Cheng, HM ;

Baker, CH ;

Matsuda, SPT ;

Li, D ;

Song, XL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (06) :1289-1296

[5] 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

[6] 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

[7] THE METHYL-GROUP AT C(10) OF 2,3-OXIDOSQUALENE IS CRUCIAL TO THE CORRECT FOLDING OF THIS SUBSTRATE IN THE CYCLIZATION REARRANGEMENT STEP OF STEROL BIOSYNTHESIS [J].

COREY, EJ ;

VIRGIL, SC ;

LIU, DR ;

SARSHAR, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1524-1525

[8] Cation-pi interactions in chemistry and biology: A new view of benzene, Phe, Tyr, and Trp [J].

Dougherty, DA .

SCIENCE, 1996, 271 (5246) :163-168

[9] ZUR KENNTNIS DER TRITERPENE .190. EINE STEREOCHEMISCHE INTERPRETATION DER BIOGENETISCHEN ISOPRENREGEL BEI DEN TRITERPENEN [J].

ESCHENMOSER, A ;

RUZICKA, L ;

JEGER, O ;

ARIGONI, D .

HELVETICA CHIMICA ACTA, 1955, 38 (07) :1890-1904

[10]

Frisch MJ., 1992, GAUSSIAN 92 DFT REVI

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