Accumulation of anthranilic acid and N-glucosylanthranilic acid by a Corynebacterium glutamicum mutant resistant to DL-serine hydroxamate

The Journal of General and Applied Microbiology

Hiroaki Takakura²  Shingo Kakita³  Kazumi Araki²  Kensuke Kawanishi²  Yoshiro Miyajima²  Yoshiteru Akashi²  Yasuo Kondo¹ 

[1] Department of Life Science and Technology, Faculty of Engineering, University of East Asia;Department of Food Technology, University of East Asia;Tokyo Research Laboratories, Kyowa Hakko Kogyo Co., Ltd.

关键词: anthranilic acid;    carboxyphenylglucosylamine;    Corynebacterium glutamicum;    glucosylanthranilic acid;    hydroxamate;    serine;    tryptophan;   

DOI  :  10.2323/jgam.45.169

学科分类：微生物学和免疫学

来源: Applied Microbiology, Molecular and Cellulrar Biosciences Research Foundation

【 摘 要 】

During a study on the effect of DL-serine hydroxamate on Corynebacterium glutamicum (JCM1318, a wild strain), a mutant resistant to the drug, strain TO3002, was isolated. This mutant accumulated five Ehrlich's reagent positive fluorescent substances in the culture medium. Two major and one minor fluorescent products were isolated by preparative high-performance liquid chromatography following charcoal column chromatography from the culture supernatant. One major product was identified as anthranilic acid whose molecular ion was confirmed to be 137 by a measurement of liquid chromatography-mass spectrometry (LC-MS), and NMR spectrum coincided with that of anthranilic acid. LC-MS spectra of another major and the minor product showed that they had the same molecular weight of 299. This major product was supported to be N-glucosylanthranilic acid (N-o-carboxyphenyl-1-β-glucosylamine) by two-dimensional 1H and 13C NMR analyses. The minor product was speculated to be an Amadori compound derived from N-glucosylanthranilic acid. N-Glucosylanthranilic acid accumulated in the early phase, then decreased in the late phase of the culture. In contrast, the accumulation of anthranilic acid increased remarkably in the late phase of the fermentation. Based on this phenomenon, it was assumed that N-glucosylanthranilic acid once accumulated was decomposed to form anthranilic acid, at least in large part, with the progress of fermentation. The strain TO3002 showed a leaky requirement for L-tryptophan or indole (but did not for anthranilic acid) and resistance to DL-serine hydroxamate.

【 授权许可】

Unknown