ENANTIOSELECTIVE REDUCTION OF RACEMIC ABSCISIC-ACID BY ASPERGILLUS-NIGER CULTURES

被引:7
作者
ARNONE, A
CARDILLO, R
NASINI, G
DEPAVA, OV
机构
[1] Dipartimento di Chimica del Politecnico, Centre del C.N.R. per le Sostanze Organiche Naturali, Politecnico di Milano, 20133 Milano
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 11期
关键词
D O I
10.1039/p19900003061
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Biotransformation of racemic abscisic acid [(±)-ABA] 1a with cultures of Aspergillus niger gives rise to the enantioselective reduction of the (S)-enantiomer to afford the corresponding (1′S,2′R)(-)- 2′,3′-dihydro-ABA acid 2a in high enantiomeric excess (e.e.). The structure, stereochemistry, and preferred conformation of compound 2a have been elucidated on the basis of NMR evidence.
引用
收藏
页码:3061 / 3063
页数:3
相关论文
共 11 条
[1]   RATIO OF (S)-ABSCISIC TO (R)-ABSCISIC ACID FROM PLANT-CELL CULTURES SUPPLIED WITH RACEMIC ABA [J].
ABRAMS, SR ;
REANEY, MJT ;
ABRAMS, GD ;
MAZUREK, T ;
SHAW, AC ;
GUSTA, LV .
PHYTOCHEMISTRY, 1989, 28 (11) :2885-2889
[2]   (+)-ABSCISIC ACID, A METABOLITE OF FUNGUS CERCOSPORA-ROSICOLA [J].
ASSANTE, G ;
MERLINI, L ;
NASINI, G .
EXPERIENTIA, 1977, 33 (12) :1556-1557
[3]   MICROBIAL TRANSFORMATIONS .12. REGIOSPECIFIC AND ASYMMETRIC OXIDATION OF THE REMOTE DOUBLE-BOND OF GERANIOL [J].
FOURNERON, JD ;
ARCHELAS, A ;
FURSTOSS, R .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (19) :4686-4689
[4]   MICROBIAL-PRODUCTION OF ABSCISIC-ACID BY BOTRYTIS-CINEREA [J].
MARUMO, S ;
KATAYAMA, M ;
KOMORI, E ;
OZAKI, Y ;
NATSUME, M ;
KONDO, S .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1982, 46 (07) :1967-1968
[5]   MICROBIAL TRANSFORMATION OF BETA-IONONE AND BETA-METHYLIONONE [J].
MIKAMI, Y ;
FUKUNAGA, Y ;
ARITA, M ;
KISAKI, T .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1981, 41 (03) :610-617
[6]   FORMATION OF (-)-1',2'-EPI-2-CIS-XANTHOXIN ACID FROM A PRECURSOR OF ABSCISIC-ACID [J].
MILBORRO.BV ;
GARMSTON, M .
PHYTOCHEMISTRY, 1973, 12 (07) :1597-1608
[7]  
MILBORROW BV, 1968, BIOCH PHYSL PLANT GR
[8]   BIOCHEMICAL REDUCTION OF TERPENES .3. CONVERSION OF (-)-CARVONE AND (+)-CARVONE BY A STRAIN OF ASPERGILLUS-NIGER [J].
NOMA, Y ;
NONOMURA, S .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1974, 38 (04) :741-744
[9]  
OHKUMA K, 1965, TETRAHEDRON LETT, P2529
[10]   STUDIES ON ABSCISIC-ACID .15. SYNTHESIS AND BIOLOGICAL-ACTIVITY OF (+-)-2',3'-DIHYDRO-ABSCISIC ACID [J].
ORITANI, T ;
YAMASHITA, K .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1982, 46 (03) :817-818