Screening of plant peptidases for the synthesis of arginine-based surfactants

Partially purified preparations with proteolytic activity, obtained from South American native plants, were used as biocatalysts in condensation reactions of N-protected arginine alkyl ester derivatives with decylamine and dodecylamine in low-water content systems. The final products are cationic su...

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Bibliographic Details
Published in:Journal of molecular catalysis. B, Enzymatic Enzymatic, 2009-05, Vol.57 (1), p.177-182
Main Authors: Morcelle, Susana R., Liggieri, Constanza S., Bruno, Mariela A., Priolo, Nora, Clapés, Pere
Format: Article
Language:English
Subjects:
Araujiain
Arginine-based surfactants
Asclepain c
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Bromelain
Enzymatic synthesis
Funastrain
Fundamental and applied biological sciences. Psychology
Hieronymain
Methods. Procedures. Technologies
Papain
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Summary:Partially purified preparations with proteolytic activity, obtained from South American native plants, were used as biocatalysts in condensation reactions of N-protected arginine alkyl ester derivatives with decylamine and dodecylamine in low-water content systems. The final products are cationic surfactants with potential application as emulsifiers and preservatives. Most of the proteolytic extracts were obtained from latex of species belonging to the Asclepiadaceae family (araujiain from Araujia hortorum, asclepain c from Asclepias curassavica and funastrain from Funastrum clausum). Hieronymain was obtained from unripe fruits of Bromelia hieronymi ( Bromeliaceae). Plant proteases from commercial sources (papain and bromelain) were also tested as catalysts in the same reactions. Araujiain and funastrain furnished good reaction conversions (60–84%, with a ratio synthesis/hydrolysis of 2–5) similar to those obtained with commercial papain. Moreover, araujiain was the biocatalyst which rendered the best conversions (60%) for the synthesis of the two novel Bz-Arg-NH-dodecylamide (Bz-Arg-NHC 12) and Bz-Arg-NH-decylamide (Bz-Arg-NHC 10) derivatives. Moderate to poor conversions (10–50%, showing a ratio synthesis/hydrolysis of 0.5–1) were achieved with asclepain c, hieronymain and bromelain. The screening presented in this work revealed that, although these are structurally similar, their behavior for the synthesis of this kind of products differ among them.
ISSN:1381-1177
1873-3158
DOI:10.1016/j.molcatb.2008.08.013