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Enzymatic Resolution of α‐Methyleneparaconic Acids and Evaluation of their Biological Activity
Author(s) -
Chakrabarty Kuheli,
Defrenza Ivana,
Denora Nunzio,
Drioli Sara,
Forzato Cristina,
Franco Massimo,
Lentini Giovanni,
Nitti Patrizia,
Pitacco Giuliana
Publication year - 2015
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22419
Subject(s) - chemistry , enantiomer , enzyme , chirality (physics) , antimicrobial , stereochemistry , antifungal , kinetic resolution , resolution (logic) , chymotrypsin , bacteria , combinatorial chemistry , biochemistry , organic chemistry , enantioselective synthesis , microbiology and biotechnology , catalysis , trypsin , genetics , artificial intelligence , computer science , biology , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Both enantiomers of three biologically relevant paraconic acids—MB‐3, methylenolactocin, and C75—were obtained with enantioselectivities up to 99% by kinetic enzymatic resolutions. Good enantiomeric excesses were obtained for MB‐3 and methylenolactocin, using α‐chymotrypsin and aminoacylase as enantiocomplementary enzymes, while C75 was resolved with aminoacylase. They all were evaluated for their antiproliferative, antibacterial, and antifungal activities, showing weak effects and practically no difference between enantiomers in each case. At high concentrations (16–64 µg/mL), (–)‐ C75 acted as an antimicrobial agent against Gram‐positive bacteria. Chirality 27:239–246, 2015 . © 2015 Wiley Periodicals, Inc.