Lipase-catalysed synthesis of olvanil in organic solvents

The release rate of vanillylamine from its hydrochloride salt was the limiting step in the lipase-catalysed synthesis of olvanil, a capsaicin analogue amide, in organic solvents. When the tertiary amine base concentration (N,N-diisopropylethylamine) was increased from 20 mM to 360 mM, the initial ra...

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Bibliographic Details
Published in:Biotechnology letters 2002-12, Vol.24 (24), p.2057-2061
Main Authors: REYES-DUARTE, Dolores, CASTILLO, Edmundo, MARTINEZ, Roberto, LOPEZ-MUNGUIA, Agustin
Format: Article
Language:English
Subjects:
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
Organic solvents
Solvents
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Summary:The release rate of vanillylamine from its hydrochloride salt was the limiting step in the lipase-catalysed synthesis of olvanil, a capsaicin analogue amide, in organic solvents. When the tertiary amine base concentration (N,N-diisopropylethylamine) was increased from 20 mM to 360 mM, the initial rate of amide synthesis increased proportionally. At a 12 molar excess of N,N-diisopropylethylamine and 30 min of preincubation, both the initial rate and total conversion were the same as those with free vanillylamine (80% conversion in 20 h). This result was independent of the organic solvent used. It is also shown that N,N-diisopropylethylamine does not enhance lipase activity.[PUBLICATION ABSTRACT]
ISSN:0141-5492
1573-6776
DOI:10.1023/A:1021371422062