FRAGMENTATION STUDIES OF D6,7-ANHIDROERITROMISIN-A BY LIQUID CHROMATOGRAPHY-MASS SPECTROSCOPY (LC-MS)

https://doi.org/10.22146/ijc.21519

Khairan Khairan(1*), Umar A. Jenie(2), Retno S. Sudibyo(3)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences,Syah Kuala University, Darussalam, Banda Aceh, 23111
(2) Faculty of Pharmacy, Universitas Gadjah Mada, Sekip Utara, Yogyakarta, 55281
(3) Faculty of Pharmacy, Universitas Gadjah Mada, Sekip Utara, Yogyakarta, 55281
(*) Corresponding Author

Abstract


Semisynthesis of D6,7-Anhydroerythromycin-A was done by biomodification technique by addition of 0.2% INH into a culture fermentation of Saccharopolyspora erythraea ATCC 11635 in medium Hutchinson. The aim of this research is to studies of fragmentation pattern from new matabolite of D6,7-Anhydroerythromycin-A by Liquid Chromatography-Mass Spectroscopy (LC-MS) and the ionization of mass spectroscopy is use by ESI (Electrospray Ionization) pattern. The FT-IR spectrometric analyzes showed a stretching vibration of C=C conjugated group at wave number 1602.7 cm-1. This C=C conjugated vibration indicated the existence of double bond between C6 and C7 (D6,7), this confirmed that isolate contained D6,7-Anhydroerythromycin-A (the possibility of D6,7 was positive). For complementation, a LC-MS (Liquid Chromatography-Mass Spectroscopy) analyzes using ESI-MS (Electrospray Ionization-Mass Spectroscopy) ionization pattern was conducted to the isolate which resulted Quassimolecular ions [M+H]+ of D7,8- and D6,7-Anhydroerythromycin-A. LC-MS spectrogram of the isolate, which gave two peaks of m/z 732.2460 and m/z 716.2522, confirmed that the m/z 732.2460 possibly was D7,8-Anhydroerythromycin-A, while the m/z 716.2502 and m/z 715.2522 possibly were D6,7-Anhydroerythromycin-A.


Keywords


isoniazid; enoyl reduction; D6,7-Anhidroeritromisin-A; fragmentation; LC-MS

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References

[1] Seno, E.T. and Hutchinson, R., 1986, The Biosynthesis of Tylosin and Erythromycin in Stephen W. Queener and L.E. Day (Ed): The Bacteria: A Treatise on Structure and Function, Academic Press Inc., Orlando, 252-270.

[2] Omura, S. and Sakakibara, 1984, Chemical Modification and Structure Activity Relationship of Macrolide in Omura S. (Ed) : Macrolide Antibiotics : Chemistry, Biology and Practise, Academic Press, Orlando, 127-194

[3] Kirst, H.A. and Sides, G., 1989, Antimicrob. Agents Chemother., 33, 9, 1413-1418.

[4] Donadio, S., Steven, N.J., Mc. Alpine, J.B., Swanson, S.J., and Kattz, L., 1991, Modular Organization of Genes Required for Complex Polyketide Biosynthesis, Research Articles, 3 May 1991, 675-679.

[5] Donadio, S., Mc. Alpine, J.B., Seldon, P.J., Jackson, M., and Kattz, L., 1993, Pro. Natl. Acad. Sci., 90, 7119-7123.

[6] Jenie, U.A., Sudibyo, R.S., and Arianingrum, R., 2003, Teknosains, 16, 1, Januari 2003, Universitas Gadjah Mada, Yogyakarta.

[7] Rozwarski, D.A., Gregory, A. Grant, and James, C.S., 1998, Science, 279, 98-102.

[8] Magliozzo, R.S. and Marcinkevicience, 1997, Am. Soc. Biotechnol. Mol. Biol., 272, 14, 8867-8879.

[9] Lee, M.S. and Kerns, E.H., 1999, Mass Spectrom. Rev., 18, 187-279.

[10] Silverstein, R.M., and Webster, F.X., 1998, Spectronic Identification of Organic Compound, Six edition, John Willey & Sons Inc., 71-110.

[11] Williams, D.H. and Fleming, I., 1997, Spectroscopic Methods in Organic Chemistry, 5th ed., Mc. Graw Hill, Cambridge. UK.



DOI: https://doi.org/10.22146/ijc.21519

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