Isolation and structure characterization of related impurities in etimicin intermediate P1 by LC/ESI-MS(n) and NMR.

Yuanchao Wang, Zhijie Zhang, Lingyun Wu, Xiaoqi Zhang, Hao Wang, Wencai Ye, Ping Li

Journal of pharmaceutical and biomedical analysis 2014 Aug

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Etimicin intermediate 3,2″,6″-N,N,N-triacetyl gentamicin C1a (P1), is a key intermediate of etimicin, which is a semi-synthetic aminoglycoside antibiotic effective to both gram-positive and gram-negative bacteria infections. Four major related impurities of P1 were detected by HPLC-ELSD and ESI-MS(n) methods. Weakly acidic cation exchange resin, CM-sephadex and silica gel column chromatography were used for the isolation and purification of four major impurities. By means of ESI-MS(n) and NMR analysis, related impurities were characterized as 3,2″-N,N-diacetyl gentamicin C1a (1), 3,2″,6″-N,N,N-triacetyl gentamicin C2b (2), 2″-N-acetyl gentamicin C1a (3), and 2″,6″-N,N-diacetyl gentamicin C1a (4). Impurities 1, 2, 4 are novel compounds and the NMR data of these isolates were first reported in this paper. The possible mechanism for the formation of these impurities is also discussed. Copyright © 2014 Elsevier B.V. All rights reserved.

Citation

Yuanchao Wang, Zhijie Zhang, Lingyun Wu, Xiaoqi Zhang, Hao Wang, Wencai Ye, Ping Li. Isolation and structure characterization of related impurities in etimicin intermediate P1 by LC/ESI-MS(n) and NMR. Journal of pharmaceutical and biomedical analysis. 2014 Aug;97:97-102