Biohydroxylations of Cbz-protected alkyl substituted piperidines by Beauveria bassiana ATCC 7159

N-Benzyloxycarbonyl (Cbz) protected piperidines are hydroxylated with greater regioselectivity than the corresponding N-benzoyl analogues when incubated with the fungus Beauveria bassiana ATCC 7159. Cbz-protected piperidines 1-3, 5-7, have been biotransformed by growing cell suspensions of this fung...

Full description

Saved in:
Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 1 no. 20; pp. 3365 - 3370
Main Authors Aitken, SJ, Grogan, G, Chow, CSY, Turner, NJ, Flitsch, SL
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1998
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MICROBIAL HYDROXYLATION
SULFURESCENS
ENANTIOMERIC EXCESS
2-CYCLOALKYLBENZOXAZOLES
FUNGAL
TRANSFORMATIONS
Online AccessGet full text

Cover

More Information
Summary:N-Benzyloxycarbonyl (Cbz) protected piperidines are hydroxylated with greater regioselectivity than the corresponding N-benzoyl analogues when incubated with the fungus Beauveria bassiana ATCC 7159. Cbz-protected piperidines 1-3, 5-7, have been biotransformed by growing cell suspensions of this fungus to yield predominantly 4-hydroxylated products in up to 48% yield. The regiospecificity of hydroxylation was only compromised significantly with N-Cbz-3-methylpiperidine 3 and N-Cbz-2-methylpiperidine 4 where hydroxylation occurred in both the 3 and 4 positions.
ISSN:0300-922X
1364-5463
DOI:10.1039/a805800h