Synthesis and enzymatic cyclization of (3S)11-fluoro-2,3-oxidosqualene

被引：31

作者：

Robustell, B

Abe, I

Prestwich, GD

机构：

[1] Univ Utah, Dept Med Chem, Salt Lake City, UT 84112 USA

[2] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 09期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(97)10669-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent asymmetric synthesis provided (3S)11-fluoro-2,3-oxidosqualene (11-FOS, 14), which was cyclized by bacterial squalene:hopane cyclase to a bridged ether. 11-FOS was neither a substrate nor an inhibitor for vertebrate oxidosqualene:lanosterol cyclase. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：957 / 960

页数：4

共 26 条

[1] MOLECULAR-CLONING, CHARACTERIZATION, AND FUNCTIONAL EXPRESSION OF RAT OXIDOSQUALENE CYCLASE CDNA
ABE, I
PRESTWICH, GD
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (20) : 9274 - 9278
[2] ENZYMATIC CYCLIZATION OF 2,3-DIHYDROSQUALENE AND SQUALENE 2,3-EPOXIDE BY SQUALENE CYCLASES - FROM PENTACYCLIC TO TETRACYCLIC TRITERPENES
ABE, I
ROHMER, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (07): : 783 - 791
[3] ABE I, 1994, J BIOL CHEM, V269, P802
[4] ENZYMATIC CYCLIZATION OF SQUALENE AND OXIDOSQUALENE TO STEROLS AND TRITERPENES
ABE, I
ROHMER, M
PRESTWICH, GD
[J]. CHEMICAL REVIEWS, 1993, 93 (06) : 2189 - 2206
[5] AFFINITY LABELING OF VERTEBRATE OXIDOSQUALENE CYCLASES WITH A TRITIATED SUICIDE SUBSTRATE
ABE, I
BAI, M
XIAO, XY
PRESTWICH, GD
[J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1992, 187 (01) : 32 - 38
[6] ABE I, 1997, IN PRESS J AM CHEM S
[7] BOUVIER P, 1980, EUR J BIOCHEM, V112, P549
[8] ASYMMETRIC DIHYDROXYLATION OF SQUALENE
CRISPINO, GA
SHARPLESS, KB
[J]. TETRAHEDRON LETTERS, 1992, 33 (30) : 4273 - 4274
[9] Cation-pi interactions in chemistry and biology: A new view of benzene, Phe, Tyr, and Trp
Dougherty, DA
[J]. SCIENCE, 1996, 271 (5246) : 163 - 168
[10] Site-directed mutagenesis of putative active-site residues in squalene-hopene cyclase
Feil, C
Sussmuth, R
Jung, G
Poralla, K
[J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1996, 242 (01): : 51 - 55

← 1 2 3 →