Highly selective biotransformation of (+)-(1S)- and (−)-(1R)-camphorquinone by Aspergillus wentii

• Published in: Biocatalysis and biotransformation Vol. 32; no. 5-6; pp. 285 - 289
• Main Authors: Usami, Atsushi, Motooka, Ryota, Miyazawa, Mitsuo
• Format: Journal Article
• Language: English
• Published: Informa Healthcare 01.12.2014; Taylor & Francis
• Subjects: (+)- and (−)-camphorquinone; Aspergillus wentii; biotransformation; stereoselective
• ISSN: 1024-2422; 1029-2446
• DOI: 10.3109/10242422.2014.975215

Abstract To clarify the structures of biotransformation products and metabolic pathways, the biotransformation of monoterpenoids, (+)- and (−)-camphorquinone (1a and b), has been investigated using Aspergillus wentii as a biocatalyst. Compound 1a was converted to (−)-(2S)-exo-hydroxycamphor (2a), (−)-(2S)-endo-hydroxycamphor (3a), (−)-(3S)-exo-hydroxycamphor (4a), (−)-(3S)-endo-hydroxycamphor (5a), and (+)-camphoric acid (6a). Compound 1b was converted to (+)-(2R)-exo-hydroxycamphor (2b), (+)-(2R)-endo-hydroxycamphor (3b), (+)-(3R)-exo-hydroxycamphor (4b), (+)-(3R)-endo-hydroxycamphor (5b), and (−)-camphoric acid (6b). Compound 1a mainly produced 2a (65.0%) with stereoselectivity, whereas 1b afforded 3b (84.3%) with high stereoselectivity. These structures were confirmed by gas chromatography-mass spectrometry, infrared, 1H nuclear magnetic resonance (NMR), and 13C NMR spectral data. The products illustrate the marked ability of A. wentii for enzymatic oxidation and ketone reduction.