BIOSYNTHESIS OF (1S)-7-METHOXY-1,2-DIHYDROCADALENE - INCORPORATION OF H-2-LABELED AND C-13-LABELED MEVALONATES BY CULTURED-CELLS OF HETEROSCYPHUS-PLANUS

被引:12
作者
NABETA, K
ISHIKAWA, T
KAWAE, T
OKUYAMA, H
机构
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 22期
关键词
D O I
10.1039/p19940003277
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
H-2 and C-13 NMR analyses of (1S)-7-methoxy-l,2-dihydrocadalene produced by cell cultures of the liverwort Heteroscyphus planus in the presence of H-2- and C-13-labelled mevalonates verified 1,2- and 1.3-hydride shifts and the hydroxylation of an aromatic ring without an NIH shift in the biosynthesis of MDC.
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页码:3277 / 3280
页数:4
相关论文
共 12 条
[1]  
ANASTASIS R, 1986, CAN J CHEM, V62, P2079
[2]   STUDIES OF AUSTRALIAN SOFT CORALS .36. THE ISOLATION AND STRUCTURE DETERMINATION OF 11 CALAMENENE-BASED SESQUITERPENES FROM LEMNALIA-CERVICORNIS (COELENTERATA, OCTOCORALLIA, ALCYONACEA) [J].
BOWDEN, BF ;
COLL, JC ;
ENGELHARDT, LM ;
TAPIOLAS, DM ;
WHITE, AH .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1986, 39 (01) :103-121
[3]  
Cane D., 1981, BIOSYNTHESIS ISOPREN, V1, P283
[4]   APPLICATION OF C-13 MAGNETIC-RESONANCE TO ISOPRENOID BIOSYNTHESIS .2. OVALICIN AND USE OF DOUBLY LABELED MEVALONATE [J].
CANE, DE ;
LEVIN, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (05) :1183-1188
[5]   HYDROXYLATION-INDUCED MIGRATION - NIH SHIFT [J].
GUROFF, G ;
DALY, JW ;
JERINA, DM ;
RENSON, J ;
WITKOP, B ;
UDENFRIE.S .
SCIENCE, 1967, 157 (3796) :1524-&
[6]   SYNTHESIS OF DL-3,5-DIHYDROXY-3-METHYLPENTANOIC ACID (MEVALONIC ACID [J].
HOFFMAN, CH ;
WAGNER, AF ;
WILSON, AN ;
WALTON, E ;
SHUNK, CH ;
WOLF, DE ;
HOLLY, FW ;
FOLKERS, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (09) :2316-2318
[7]  
NABETA K, 1993, PHYTOCHEMISTRY, V32, P117
[8]   BIOSYNTHESIS OF SESQUITERPENES OF CADINANE TYPE IN CULTURED-CELLS OF HETEROSCYPHUS-PLANUS [J].
NABETA, K ;
MOTOTANI, Y ;
TAZAKI, H ;
OKUYAMA, H .
PHYTOCHEMISTRY, 1994, 35 (04) :915-920
[9]   REGIOSPECIFICITY AND ISOTOPE EFFECTS ASSOCIATED WITH THE METHYL METHYLENE ELIMINATIONS IN THE ENZYME-CATALYZED BIOSYNTHESIS OF (R)-LIMONENE AND (S)-LIMONENE [J].
PYUN, HJ ;
COATES, RM ;
WAGSCHAL, KC ;
MCGEADY, P ;
CROTEAU, RB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3998-4009
[10]   3,10-DIHYDRO-1,4-DIMETHYLAZULENE, A LABILE BIOSYNTHETIC INTERMEDIATE ISOLATED FROM CULTURED-CELLS OF LIVERWORT CALYPOGEIA-GRANULATA INOUE [J].
TAKEDA, R ;
KATOH, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) :4056-4058