Appl Environ Microbiol. 1996 Mar;62(3):749-55. doi: 10.1128/aem.62.3.749-755.1996.
Rhodococcus rhodochrous PB1 was isolated from compost soil by selective culture with racemic 3-phenylbutyric acid as the sole carbon and energy source. Growth experiments with the single pure enantiomers as well as with the racemate showed that only one of the two enantiomers, (R)-3-phenylbutyric acid, supported growth of strain PB1. Nevertheless, (S)-3-phenylbutyric acid was cometabolically transformed to, presumably, (S)-3-(2,3-dihydroxyphenyl)butyric acid (the absolute configuration at the C-3 atom is not known yet) by (R)-3-phenylbutyric acid-grown cells of strain PB1, as shown by (sup1)H nuclear magnetic resonance spectroscopy of the partially purified compound and gas chromatography-mass spectrometry analysis of the trimethylsilyl derivative. Oxygen uptake rates suggest that either 3-phenylpropionic acid or cinnamic acid (trans-3-phenyl-2-propenoic acid) is the substrate for aromatic ring hydroxylation. This view is substantiated by the fact that 3-(2,3-dihydroxyphenyl)propionic acid was a substrate for meta cleavage in cell extracts of (R)-3-phenylbutyric acid-grown cells of strain PB1. Gas chromatography-mass spectrometry analysis of trimethylsilane-treated ethyl acetate extracts of incubation mixtures showed that both the meta-cleavage product, 2-hydroxy-6-oxo-2,4-nonadiene-1,9-dicarboxylic acid, and succinate, a hydrolysis product thereof, were formed during such incubations.
从堆肥土壤中通过选择性培养分离出玫瑰红红球菌 PB1，以消旋 3-苯基丁酸作为唯一的碳源和能源。用单一纯对映体以及外消旋体进行生长实验表明，只有两种对映体之一，（R）-3-苯基丁酸，支持 PB1 菌株的生长。然而，（S）-3-苯基丁酸被（R）-3-苯基丁酸生长的 PB1 菌株细胞共代谢转化为（S）-3-（2,3-二羟基苯基）丁酸（C-3 原子的绝对构型尚不清楚），这一点通过部分纯化化合物的（sup1）H 核磁共振光谱和三甲基硅衍生物的气相色谱-质谱分析得到证实。氧摄取率表明 3-苯基丙酸或肉桂酸（反式-3-苯基-2-丙烯酸）是芳环羟化的底物。这一观点得到了以下事实的证实：3-（2,3-二羟基苯基）丙酸是 PB1 菌株（R）-3-苯基丁酸生长细胞提取物中间位裂解的底物。孵育混合物的三甲基硅烷处理的乙酸乙酯提取物的气相色谱-质谱分析表明，在这些孵育过程中形成了间位裂解产物 2-羟基-6-氧代-2,4-壬二烯-1,9-二酸和其水解产物琥珀酸。
