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首页> 外文期刊>Journal of bacteriology >Structure of the Ring Cleavage Product of 1-Hydroxy-2-Naphthoate, an Intermediate of the Phenanthrene-Degradative Pathway ofNocardioides sp. Strain KP7
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Structure of the Ring Cleavage Product of 1-Hydroxy-2-Naphthoate, an Intermediate of the Phenanthrene-Degradative Pathway ofNocardioides sp. Strain KP7

机译：1-羟基-2-萘甲酸酯的环裂解产物的结构，诺卡氏菌sp的菲-降解途径的中间体。 KP7株

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摘要

1-Hydroxy-2-naphthoate (compound I) is a metabolite of the phenanthrene-degradative pathway in Nocardioides sp. strain KP7. This singly hydroxylated aromatic compound is cleaved by 1-hydroxy-2-naphthoate dioxygenase. In this study, the structure of the ring cleavage product generated by the action of homogeneous 1-hydroxy-2-naphthoate dioxygenase was determined upon separation by high-performance liquid chromatography at pH 2.5 by using nuclear magnetic resonance (NMR) and mass spectroscopic techniques. The ring cleavage product at this pH existed in equilibrium between two forms, 2-oxo-3-(3-oxo-1,3-dihydro-1-isobenzofuranyl)propanoate (compound III) and 2,2-dihydroxy-3-(3-oxo-1,3-dihydro-1-isobenzofuranyl)propanoate (compound IV). After the pH of the solution was raised to 7.5, the structure of the major species became (E)-4-(2-carboxylatophenyl)-2-oxo-3-butenoate (compound II; common name, trans-2′-carboxybenzalpyruvate), which was in equilibrium with compound III. Direct monitoring of the enzymatic formation of the ring cleavage product by 1H-NMR in a deuterated potassium phosphate buffer (pH 7.5) detected only compound II as a product, and the proton on carbon 3 of compound II was not exchanged with deuterium. Thus, compound II is likely to be the first stable product of dioxygenation of 1-hydroxy-2-naphthoate.
机译：1-羟基-2-萘甲酸酯（化合物I）是 Nocardioides sp中菲降解途径的代谢物。菌株KP7。该单羟基化的芳族化合物被1-羟基-2-萘甲酸双加氧酶裂解。在这项研究中，通过使用核磁共振（NMR）和质谱技术在高效液相色谱法（pH 2.5）上进行分离，确定了由均相的1-羟基-2-萘甲酸双加氧酶的作用产生的环裂解产物的结构。 。在此pH值下，环裂解产物在两种形式（2-氧代-3-（3-氧代-1,3-二氢-1-异苯并呋喃基）丙酸酯（化合物III）和2,2-二羟基-3-（ 3-氧代-1,3-二氢-1-异苯并呋喃基）丙酸酯（化合物IV）。溶液的pH值升至7.5后，主要物质的结构变为（ E ）-4-（2-羧甲基苯基）-2-氧代-3-丁烯酸酯（化合物II;通用名， trans -2'-羧苯并丙酮酸），与化合物III处于平衡状态。通过氘化磷酸钾缓冲液（pH 7.5）中的 1 H-NMR直接监测环裂解产物的酶促形成，仅检测到化合物II为产物，而质子在化合物II的碳3上没有与氘交换。因此，化合物II很可能是1-羟基-2-萘甲酸双加氧的第一稳定产物。

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