Microbial hydroxylation of chiral bicyclic enones by Chaetomium sp.1 and Didymosphaeria igniaria cultures

Biocatalysis and Biotransformation

Volumn 24, Issue 6, 2006, Pages 458-463

  Janeczko, Tomasz ^a   Dmochowska Gładysz, Jadwiga ^a   Białońska, Agata ^b   Ciunik, Zbigniew ^b  

^a WROC AW UNIVERSITY OF ENVIRONMENTAL AND LIFE SCIENCES   (Poland)

^b UNIVERSITY OF WROC AW   (Poland)

Author keywords

Bicyclic enones; Biotransformations; Chaetomium sp.1; Didymosphaeria igniaria; Enantiomeric resolution; Hydroxylation

Indexed keywords

DERIVATIVES; HYDROXYLATION; MICROBIOLOGY;

BICYCLIC ENONES; BIOTRANSFORMATIONS; DIDYMOSPHAERIA IGNIARIA; ENANTIOMERIC RESOLUTION;

BIOCATALYSTS;

4,4A,5,6,7,8 HEXAHYDRO 3ALPHA HYDROXY 4A METHYL 2(3H) NAPHTHALENONE; 4,4A,5,6,7,8 HEXAHYDRO 4A METHYLNAPHTHALEN 2(3H) ONE; 4,4A,5,6,7,8 HEXAHYDRO 4BETA HYDROXY 4A METHYL 2(3H) NAPHTHALENONE; 4,4A,5,6,7,8 HEXAHYDRO 6BETA HYDROXY 4A METHYL 2(3H) NAPHTHALENONE; 4,4A,5,6,7,8 HEXAHYDRO 7BETA HYDROXY 4A METHYL 2(3H) NAPHTHALENONE; 4,4A,5,6,7,8 HEXAHYDRO 8ALPHA HYDROXY 4A METHYL 2(3H) NAPHTHALENONE; 4,4A,5,6,7,8 HEXAHYDRO 8BETA HYDROXY 4A METHYL 2(3H) NAPHTHALENONE; ENONE DERIVATIVE; METHYLOCTALONE; NAPHTHALENE; NAPHTHALENE DERIVATIVE;

ARTICLE; BIOCATALYST; BIOTRANSFORMATION; CHAETOMIUM; CHEMICAL STRUCTURE; CHIRALITY; CULTURE MEDIUM; DIDYMOSPHAERIA IGNIARIA; ENANTIOMER; FUNGAL STRAIN; FUNGUS CULTURE; HYDROXYLATION; INCUBATION TIME; STRUCTURE ANALYSIS;

CHAETOMIUM; VERRUCULINA;

EID: 33845515669     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.1080/10242420601100214     Document Type: Article

References (17)

1. Baptistella, LHB and Aleixo, AM. (2002) α'-Hydroxy-α, β-unsaturated tosylhydrazones: Preparation and use as intermediates for carbonyl and enone transpositions Synth Commun, 32, pp. 2937-2950.
2. Bartmańska, A and Dmochowska-Gíadysz, J and Huszcza, E. (2004) Steroids' transformations in Penicillium notatum culture Steroids, 70, pp. 193-198.
3. Bruker AXS, SHELXTL V5.1, 1999.
4. Collins, DO and Reese, PB. (2001) Biotransformation of cadina-4,10(15)-dien-3-on and 3α-hydroksycadina-4,10(15)-dien by Curvularia lunata ATCC 12017 Phytochemistry, 59, pp. 489-492.
5. Estour, F and Menager, S and Akagah, B and Lafont, O. (2003) Comparison of the efficiency of various methods for the synthesis of models of metabolites: Example of 4a-methylhexahydronaphtalenes Eur J Med Chem, 38, pp. 925-928.
6. Garcia-Granados, A and Martinez, A and Honorato, ME and Rias, F and Arias, JM. (1991) Chemical-microbiological synthesis of 6α-eudesmanolides by Curvularia lunata cultures from eudesmanes with functions at C-1 and C-6 Tetrahedron, 1, pp. 91-102.
7. Hammoumi, A and Girault, J-P and Azerad, R. (1993) Microbial hydroxylation and functionalization of synthetic polycyclic enones Tetrahedron: Asymmetry, 4, pp. 1295-1306.
8. Hammoumi, A and Revial, G and D'Angelo, J and Girault, JP and Azerad, R. (1991) Microbial hydroxylation and functionalization of synthetic bicyclic enones Tetrahedron Lett, 5, pp. 651-654.
9. Holland, HL. (1984) Biotransformations of delta 4-3-ketosteroids by the fungus Rhizopus arrhizus Acc Chem Res, 17, pp. 398-402.
10. Ouazzani, J and Arseniyadis, S and Alvarea-Manzaneda, R and Cabrera, E and Ourisson, G. (1991) Microbial allylic hydroxylation of some octalone derivatives Tetrahedron Lett, 5, pp. 647-650.
11. Oxford Diffraction, Poland Sp. z o.o, CrysAlis CCD and CrysAlis Red, V166, 2001.
12. Parvez, A and Hanson, JR. (2004) The hydroxylation of the enantiomeric hexahydro-10-methylnaphthal-4-en-3-ones by Cephalosporium aphidicola J Chem Res, 9, pp. 647-648.
13. Prelog, V. (1964) Specification of the stereospecificity of some oxido-reductases by diamond lattice sections Pure Appl Chem, 9, pp. 119-130.
14. Segrestaa, J and Vérité, P and Estour, F and Ménager, S and Lafont, O. (2002) Improvement of a biomimetic porphyrin catalytic system by addition of acids Chem Pharm Bull, 50, pp. 744-748.
15. Shono, T and Toda, T and Oshino, N. (1984) Electrooxidative simulation of stereoselectivity in microsomal allylic hydroxylation Tetrahedron Lett, 25, pp. 91-94.
16. Świzdor, A and Kołek, T. (2005) Transformations of 4- and 17α-substituted testosterone analogues by Fusarium culmorum Steroids, 70, pp. 817-834.
17. Vérité, P and Ménager, S and Cavé, C and André, D and d'Angelo, J and Revial, G and Farnoux, CC and Lafont, O. (1997) Regio- and stereoselective aspects in the oxidation of (R) and (S) 4a-methyl-(4,4a,5,6,7,8)-hexahydro-2(3H)-naphthalenones in living rats Bioorg Med Chem Lett, 7, pp. 587-592.