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Gu Y, Ni X, Ren J, et al. Biosynthesis of Epimers C2 and C2a in the Gentamicin C Complex. Chembiochem. 2015;16(13):1933-1942doi: 10.1002/cbic.201500258.
Gu, Y., Ni, X., Ren, J., Gao, H., Wang, D., & Xia, H. (2015). Biosynthesis of Epimers C2 and C2a in the Gentamicin C Complex. Chembiochem : a European journal of chemical biology, 16(13), 1933-1942. https://doi.org/10.1002/cbic.201500258
Gu, Yawen, et al. "Biosynthesis of Epimers C2 and C2a in the Gentamicin C Complex." Chembiochem : a European journal of chemical biology vol. 16,13 (2015): 1933-1942. doi: https://doi.org/10.1002/cbic.201500258
Gu Y, Ni X, Ren J, Gao H, Wang D, Xia H. Biosynthesis of Epimers C2 and C2a in the Gentamicin C Complex. Chembiochem. 2015 Sep 07;16(13):1933-1942. doi: 10.1002/cbic.201500258. Epub 2015 Jul 14. PMID: 26083124.
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Chembiochem. 2015 Sep 07;16(13):1933-1942. doi: 10.1002/cbic.201500258. Epub 2015 Jul 14.

Biosynthesis of Epimers C2 and C2a in the Gentamicin C Complex.

Chembiochem : a European journal of chemical biology

Yawen Gu, Xianpu Ni, Jun Ren, Huiyuan Gao, Da Wang, Huanzhang Xia

Affiliations

  1. School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenyang 110016 (P. R. China).
  2. Key Laboratory of Structure-Based Drug Design, and Discovery of Ministry of Education, School of Traditional Chinese Material Medica, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenyang 110016 (P. R. China).

PMID: 26083124 DOI: 10.1002/cbic.201500258

Abstract

Gentamicin is a broad-spectrum aminoglycoside antibiotic widely used to treat life-threatening bacterial infections. The gentamicin C complex consists of gentamicin C1, gentamicin C1a, and epimers gentamicin C2 and gentamicin C2a. At present there is a generally accepted pathway of gentamicin biosynthesis, except for detailed understanding of the epimerization process involving gentamicins C2 and C2a. Here we have investigated the biosynthesis of these epimers. JI-20B-an intermediate in the gentamicin biosynthetic pathway-and its epimer JI-20Ba were generated by in-frame deletion within genP, which encodes a phosphotransferase that catalyzes the first step of 3',4'-bisdehydroxylation in gentamicin biosynthesis. GenB1 and GenB2 are aminotransferases with different substrate specificities and enantioselectivities. JI-20Ba, containing a 6'S chiral amine, a precursor of gentamicin C2a, was synthesized from G418 by GenQ/GenB1 through sequential oxidation/transamination at C-6'. GenQ/GenB2 catalyzed the synthesis of JI-20B, containing a 6'R chiral amine, a precursor of gentamicin C2, from G418. GenB2 catalyzed the epimerization of JI-20Ba/JI-20B and of gentamicins C2a/C2.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: aminoglycosides; antibiotics; biosynthesis; epimers; stereoisomerization; transamination

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