title: Enzymatic resolution of α-methyleneparaconic acids and evaluation of their biological activity.
abstract: 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.
authors.affiliation: Department of Chemistry, Visva-Bharati, Santiniketan, India.
authors.forename: Kuheli
authors.initials: K
authors.lastname: Chakrabarty
authors.forename: Ivana
authors.initials: I
authors.lastname: Defrenza
authors.forename: Nunzio
authors.initials: N
authors.lastname: Denora
authors.forename: Sara
authors.initials: S
authors.lastname: Drioli
authors.forename: Cristina
authors.initials: C
authors.lastname: Forzato
authors.forename: Massimo
authors.initials: M
authors.lastname: Franco
authors.forename: Giovanni
authors.initials: G
authors.lastname: Lentini
authors.forename: Patrizia
authors.initials: P
authors.lastname: Nitti
authors.forename: Giuliana
authors.initials: G
authors.lastname: Pitacco
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D000581:Amidohydrolases / Q000378:metabolism; D000890:Anti-Infective Agents / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000494:pharmacology*; D002918:Chymotrypsin / Q000378:metabolism; D006801:Humans; D061986:MCF-7 Cells; D013237:Stereoisomerism
chemical_list: D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; C571316:paraconic acid; D002918:Chymotrypsin; C117608:alpha-chymotrypsin; D000581:Amidohydrolases; C019672:aminoacylase I; D015107:4-Butyrolactone
keywords: C75; MB-3, methylenolactocin; α-methylene-γ-butyrolactones