SUBSTITUTION OF THE METHYL-GROUPS WITH ETHYL GROUPS AT C-10 AND C-15 OF 2,3-OXIDOSQUALENE HALTS THE ENZYMATIC-REACTION OF OXIDOSQUALENE-LANOSTEROL CYCLASE AT THE MONOCYCLIC RING STAGE

被引:14
作者
HOSHINO, T
ISHIBASHI, E
KANEKO, K
机构
[1] NIIGATA COLL PHARM,NIIGATA 95021,JAPAN
[2] NIIGATA UNIV,FAC AGR,DEPT APPL BIOL CHEM,NIIGATA 95021,JAPAN
关键词
D O I
10.1039/C39950002401
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Incubation of the substrate analogue, (3S)-(E,E,E,E,E)-10,15-diethyl-2,6,19,23 6,10,14,18,22-pentaene (-)-1, with 2,3-oxidosqualene-lanosterol cyclase from pigs liver gave unprecedented cyclization products 2 and 3 having a monocyclic skeleton.
引用
收藏
页码:2401 / 2402
页数:2
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]   AFFINITY LABELING OF VERTEBRATE OXIDOSQUALENE CYCLASES WITH A TRITIATED SUICIDE SUBSTRATE [J].
ABE, I ;
BAI, M ;
XIAO, XY ;
PRESTWICH, GD .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1992, 187 (01) :32-38
[3]   ACHILLEOL-A - A NEW MONOCYCLIC TRITERPENE SKELETON FROM ACHILLEA-ODORATA L [J].
BARRERO, AF ;
ALVAREZMANZANEDA, EJ ;
ALVAREZMANZANEDA, R .
TETRAHEDRON LETTERS, 1989, 30 (25) :3351-3352
[4]   ENANTIOSELECTIVE ENZYMATIC STEROL SYNTHESIS BY ULTRASONICALLY STIMULATED BAKERS-YEAST [J].
BUJONS, J ;
GUAJARDO, R ;
KYLER, KS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :604-606
[5]   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
[6]   PARTIAL-PURIFICATION AND CHARACTERIZATION OF OXIDOSQUALENE-LANOSTEROL CYCLASE FROM BAKERS-YEAST [J].
HOSHINO, T ;
WILLIAMS, HJ ;
CHUNG, YS ;
SCOTT, AI .
TETRAHEDRON, 1991, 47 (31) :5925-5932
[7]   INHIBITORY ACTIVITY OF 8-AZADECALIN DERIVATIVES TOWARDS 2,3-OXIDOSQUALENE-LANOSTEROL CYCLASES FROM BAKERS-YEAST AND PIGS LIVER [J].
HOSHINO, T ;
KOBAYASHI, N ;
ISHIBASHI, E ;
HASHIMOTO, S .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1995, 59 (04) :602-609
[8]   SYNTHESIS OF 10,15-[(C-13)2]-SQUALENE AND 10,15-[(C-13)2]-DL-SQUALENE OXIDE [J].
HOSHINO, T ;
WILLIAMS, HJ ;
SHISHIDO, K ;
SCOTT, AI .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1990, 28 (11) :1285-1292
[9]   ENZYMATIC CYCLIZATION OF HYDROXYLATED SURROGATE SQUALENOIDS WITH BAKERS-YEAST [J].
MEDINA, JC ;
KYLER, KS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4818-4821
[10]   VINYL GROUP REARRANGEMENT IN THE ENZYMATIC CYCLIZATION OF SQUALENOIDS - SYNTHESIS OF 30-OXYSTEROLS [J].
MEDINA, JC ;
GUAJARDO, R ;
KYLER, KS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (06) :2310-2311