Unnatural natural triterpenes produced by altering isoleucine into alanine at position 261 in hopene synthase and the importance of having the appropriate bulk size at this position for directing the stereochemical destiny during the polycyclization cascade

被引:40
作者
Hoshino, T [1 ]
Abe, T
Kouda, M
机构
[1] Niigata Univ, Fac Agr, Dept Appl Biol Chem, Niigata 9502181, Japan
[2] Niigata Univ, Grad Sch Sci & Technol, Niigata 9502181, Japan
关键词
D O I
10.1039/b000711k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Incubation of squalene with the site-directed mutant of Ile261Ala of squalene-hopene cyclase from Alicyclobacillus acidocaldarius afforded multiple triterpenes consisting of tri-, tetra- and penta-cyclic skeletons, together with a final product of hopene, among which the previously unknown 6/6/6/6-fused tetracyclic skeletal compounds, denoted prohopene A and B, are included.
引用
收藏
页码:441 / 442
页数:2
相关论文
共 15 条
[1]   ENZYMATIC CYCLIZATION OF 2,3-DIHYDROSQUALENE AND SQUALENE 2,3-EPOXIDE BY SQUALENE CYCLASES - FROM PENTACYCLIC TO TETRACYCLIC TRITERPENES [J].
ABE, I ;
ROHMER, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (07) :783-791
[2]   ENZYMATIC CYCLIZATION OF SQUALENE AND OXIDOSQUALENE TO STEROLS AND TRITERPENES [J].
ABE, I ;
ROHMER, M ;
PRESTWICH, GD .
CHEMICAL REVIEWS, 1993, 93 (06) :2189-2206
[3]  
AGETA H, 1987, CHEM PHARM BULL, V35, P2705
[4]  
ARAI Y, 1982, CHEM PHARM BULL, V30, P4219
[5]   Trichodiene synthase. Enzymatic formation of multiple sesquiterpenes by alteration of the cyclase active site [J].
Cane, DE ;
Xue, Q .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (06) :1563-1564
[6]   Functional analysis of phenylalanine 365 in hopene synthase, a conserved amino acid in the families of squalene and oxidosqualene cyclases [J].
Hoshino, T ;
Sato, T .
CHEMICAL COMMUNICATIONS, 1999, (19) :2005-2006
[7]   New cyclization mechanism for squalene: a ring-expansion step for the five-membered C-ring intermediate in hopene biosynthesis [J].
Hoshino, T ;
Kouda, M ;
Abe, T ;
Ohashi, S .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1999, 63 (11) :2038-2041
[8]  
MASUDA K, 1989, CHEM PHARM BULL, V37, P1140
[9]   Multiple genetic modifications of the erythromycin polyketide synthase to produce a library of novel "unnatural" natural products [J].
McDaniel, R ;
Thamchaipenet, A ;
Gustafsson, C ;
Fu, H ;
Betlach, M ;
Betlach, M ;
Ashley, G .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (05) :1846-1851
[10]   Altered product pattern of a squalene-hopene cyclase by mutagenesis of active site residues [J].
Merkofer, T ;
Pale-Grosdemange, C ;
Wendt, KU ;
Rohmer, M ;
Poralla, K .
TETRAHEDRON LETTERS, 1999, 40 (11) :2121-2124