Enantioselective Baeyer-Villiger oxidation of bicyclo[3.2.0]hept-2-en-6-One with fungi: optimization of biotransformation and use of TiO2 as support of cell growth.
Fungi from Amazonian forest soil (Ecuador) and an Italian factory were screened for Baeyer-Villiger (BV) oxidation of bicyclo [3.2.0]hept-2-en-6-one to 2-oxabicyclo[3.3.0]oct-6-en-3-one (Corey's lactone). Isolates of Fusarium sp. and F. solani produced the (+)-(1R,5S)-lactone while isolates of Aspergillus terricola and A. amazonicus afforded the (-)-(1S,5R)-lactone. Highest conversions (85% yield and 70% enantiomeric excess) were obtained with A. amazonicus grown in presence of 2.7 mM titanium dioxide.
Fantin
Giancarlo
G
Dipartimento di Chimica, Università di Ferrara, Via L. Borsari 46, I-44100 Ferrara, Italy.
Giovannini
Pier Paolo
PP
Guerrini
Alessandra
A
Maietti
Silvia
S
Medici
Alessandro
A
Pedrini
Paola
P
D001230:Aspergillus / Q000254:growth & development / Q000378:metabolism*; D001711:Biotransformation / Q000502:physiology; D001643:Bridged Bicyclo Compounds / Q000378:metabolism*; D005670:Fusarium / Q000254:growth & development / Q000378:metabolism*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014025:Titanium
D001643:Bridged Bicyclo Compounds; C472066:bicyclo(3,2,0)hept-2-en-6-one; C009495:titanium dioxide; D014025:Titanium