Efficient production of (R)-3-hydroxycarboxylic acids by biotechnological conversion of polyhydroxyalkanoates and their purification.
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.
Ruth
Katinka
K
Laboratories for Biomaterials, Swiss Federal Laboratories for Materials Testing and Research, Lerchenfeldstrasse 5, CH-9014 St. Gallen, Switzerland.
Grubelnik
Andreas
A
Hartmann
René
R
Egli
Thomas
T
Zinn
Manfred
M
Ren
Qun
Q
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
D000473:Alkanes; D000890:Anti-Infective Agents; D002264:Carboxylic Acids; D046911:Macromolecular Substances; D012997:Solvents; D002244:Carbon