title: Efficient production of (R)-3-hydroxycarboxylic acids by biotechnological conversion of polyhydroxyalkanoates and their purification.
abstract: An efficient method to prepare enantiomerically pure (R)-3-hydroxycarboxylic acids from bacterial polyhydroxyalkanoates (PHAs) accumulated by Pseudomonas putida GPo1 is reported in this study. (R)-3-Hydroxycarboxylic acids from whole cells were obtained when conditions were provided to promote in vivo depolymerization of intracellular PHA. The monomers were secreted into the extracellular environment. They were separated and purified by acidic precipitation, preparative reversed-phase column chromatography, and subsequent solvent extraction. Eight (R)-3-hydroxycarboxylic acids were isolated: (R)-3-hydroxyoctanoic acid, (R)-3-hydroxyhexanoic acid, (R)-3-hydroxy-10-undecenoic acid, (R)-3-hydroxy-8-nonenoic acid, (R)-3-hydroxy-6-heptenoic acid, (R)-3-hydroxyundecanoic acid, (R)-3-hydroxynonanoic acid, and (R)-3-hydroxyheptanoic acid. The overall yield based on released monomers was around 78 wt % for (R)-3-hydroxyoctanoic acid. All obtained monomers had a purity of over 95 wt %. The physical properties of the purified monomers and their antimicrobial activities were also investigated.
authors.affiliation: Laboratories for Biomaterials, Swiss Federal Laboratories for Materials Testing and Research, Lerchenfeldstrasse 5, CH-9014 St. Gallen, Switzerland.
authors.forename: Katinka
authors.initials: K
authors.lastname: Ruth
authors.forename: Andreas
authors.initials: A
authors.lastname: Grubelnik
authors.forename: René
authors.initials: R
authors.lastname: Hartmann
authors.forename: Thomas
authors.initials: T
authors.lastname: Egli
authors.forename: Manfred
authors.initials: M
authors.lastname: Zinn
authors.forename: Qun
authors.initials: Q
authors.lastname: Ren
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D000890:Anti-Infective Agents / Q000737:chemistry; D001709:Biotechnology / Q000379:methods*; D002152:Calorimetry, Differential Scanning / Q000379:methods; D002244:Carbon / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D002845:Chromatography / Q000379:methods; D002849:Chromatography, Gas / Q000379:methods; D002853:Chromatography, Liquid / Q000379:methods; D046911:Macromolecular Substances; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D016958:Pseudomonas putida / Q000378:metabolism; D012997:Solvents / Q000737:chemistry
chemical_list: D000473:Alkanes; D000890:Anti-Infective Agents; D002264:Carboxylic Acids; D046911:Macromolecular Substances; D012997:Solvents; D002244:Carbon