Morawski B, Eaton R W, Rossiter J T, Guoping S, Griengl H, Ribbons D W
Institute of Organic Chemistry, SFB Biocatalysis, Technical University Graz, Austria.
J Bacteriol. 1997 Jan;179(1):115-21. doi: 10.1128/jb.179.1.115-121.1997.
Burkholderia strain (JT 1500), able to use 2-naphthoate as the sole source of carbon, was isolated from soil. On the basis of growth characteristics, oxygen uptake experiments, enzyme assays, and detection of intermediates, a degradation pathway of 2-naphthoate is proposed. The features of this pathway are convergent with those for phenanthrene. We propose a pathway for the conversion of 2-naphthoate to 1 mol (each) of pyruvate, succinate, and acetyl coenzyme A and 2 mol of CO2. During growth in the presence of 2-naphthoate, six metabolites were detected by thin-layer chromatography, high-performance liquid chromatography, and spectroscopy. 1-Hydroxy-2-naphthoate accumulated in the culture broth during growth on 2-naphthoate. Also, the formation of 2'-carboxybenzalpyruvate, phthalaldehydate, phthalate, protocatechuate, and beta-carboxy-cis,cis-muconic acid was demonstrated. (1R,2S)-cis-1,2-Dihydro-1,2-dihydroxy-2-naphthoate was thus considered an intermediate between 2-naphthoate and 1-hydroxy-2-naphthoate, but it was not transformed by whole cells or their extracts. We conclude that this diol is not responsible for the formation of 1-hydroxy-2-naphthoate from 2-naphthoate but that one of the other three diastereomers is not eliminated as a potential intermediate for a dehydration reaction.
从土壤中分离出能够以2-萘甲酸盐作为唯一碳源的伯克霍尔德氏菌菌株(JT 1500)。基于生长特性、氧摄取实验、酶分析以及中间体的检测,提出了2-萘甲酸盐的降解途径。该途径的特征与菲的降解途径相似。我们提出了一条将2-萘甲酸盐转化为1摩尔(各)丙酮酸、琥珀酸和乙酰辅酶A以及2摩尔二氧化碳的途径。在2-萘甲酸盐存在下生长期间,通过薄层色谱、高效液相色谱和光谱法检测到六种代谢物。在以2-萘甲酸盐为碳源生长时,1-羟基-2-萘甲酸盐在培养液中积累。此外,还证实了2'-羧基苯甲酰丙酮酸、邻苯二甲醛、邻苯二甲酸盐、原儿茶酸和β-羧基-顺,顺-粘康酸的形成。因此,(1R,2S)-顺式-1,2-二氢-1,2-二羟基-2-萘甲酸盐被认为是2-萘甲酸盐和1-羟基-2-萘甲酸盐之间的中间体,但它不能被完整细胞或其提取物转化。我们得出结论,这种二醇不是2-萘甲酸盐形成1-羟基-2-萘甲酸盐的原因,但其他三种非对映异构体之一作为脱水反应的潜在中间体的可能性并未排除。