Enantiomeric purity of 3-phenyl-4,4-dimethyl-1-pentene. Chemical interrelation between the maximum rotations of .alpha.-tert-butylphenylacetic acid and .beta.-tert-butyl-.beta.-phenylpropionic acid

1972 ◽  
Vol 37 (7) ◽  
pp. 1060-1062 ◽  
Author(s):  
L. Lardicci ◽  
R. Menicagli
Keyword(s):  
Enantiomeric Purity ◽  
Phenylpropionic Acid ◽  
Tert Butyl

Microbial oxidation of benzyl sulfides and bibenzyl by Mortierella isabellina and Helminthosporium species

1991 ◽  
Vol 69 (12) ◽  
pp. 1989-1993 ◽  
Author(s):  
Herbert L. Holland ◽  
Cynthia G. Rand ◽  
Peter Viski ◽  
Frances M. Brown
Keyword(s):  
Key Words ◽  
Enantiomeric Purity ◽  
Time Dependent ◽  
Dependent Manner ◽  
Microbial Oxidation ◽  
Mortierella Isabellina ◽  
Tert Butyl ◽  
Biotransformation Enzymes ◽  
Oxidation Reduction ◽  
General Preference

The biotransformation of 1,2-diphenylethane by the fungus Mortierella isabellina ATCC 42613, and that of a series of alkyl benzyl sulfides by the fungi M. isabellina and Helminthosporium species NRRL 4671 have been studied. Mortierella hydroxylates 1,2-diphenylethane in low yield, giving (S)-1,2-diphenylethanol with an enantiomeric purity of 33%. Bioconversions of deuterium-labelled and racemic 1,2-diphenylethanol by M. isabellina demonstrate that this organism performs reversible oxidation/reduction of the alcohol. Biotransformations of n-alkyl benzyl sulfides by H. species give predominantly the (S) enantiomer of sulfoxide, with no sulfone formation, but M. isabellina, although showing a general preference for the oxidation of alkyl benzyl sulfides to (R) sulfoxides, also generates sulfones from n-alkyl benzyl sulfides in a time-dependent manner that suggests a stereoselective removal of (R) sulfoxide. The latter microorganism can be used, however, for the production of (R)-benzyl methyl and benzyl isopropyl sulfoxides, and gives (S)-benzyl tert-butyl sulfoxide in low yield. Key words: biotransformation, enzymes, sulfoxides.

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