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Antibiotics 2017, 6(1), 7; doi:10.3390/antibiotics6010007

Final Demonstration of the Co-Identity of Lipiarmycin A3 and Tiacumicin B (Fidaxomicin) through Single Crystal X-ray Analysis

1
Consiglio Nazionale delle Ricerche (C.N.R.), Istituto di Chimica del Riconoscimento Molecolare; Via L. Mancinelli 7, I-20131 Milano, Italy
2
Dipartimento di Chimica, Materiali ed Ingegneria Chimica del Politecnico, Via Mancinelli 7, I-20131 Milano, Italy
3
OLON S.p.A, Strada Rivoltana 6/7, 20090 Rodano, Italy
*
Author to whom correspondence should be addressed.
Academic Editor: Naresh Kumar
Received: 20 December 2016 / Revised: 22 January 2017 / Accepted: 30 January 2017 / Published: 8 February 2017
(This article belongs to the Special Issue Antibiotic Synthesis)
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Abstract

Lipiarmycin A3 and tiacumicin B possess the same chemical structure and have been considered identical till recently, when some authors have suggested the possibility of a minor difference between the chemical structures of the two antibiotics. In this work we performed a comparative X-ray analysis of lipiarmycin A3 and tiacumicin B. Although the commercial samples of the aforementioned compounds crystallize into two different crystal systems—evidently due to the different crystallization conditions—their chemical structures are identical. These results confirmed the previous assigned chemical structure of lipiarmycin A3 and its absolute configuration as well as its co-identity with the chemical structure of tiacumicin B, providing the definitive proof that these pharmaceutical compounds are identical in all respects. View Full-Text
Keywords: actinomycetes; antibiotic; fidaxomicin; lipiarmycin A3; tiacumicin B; X-ray analysis actinomycetes; antibiotic; fidaxomicin; lipiarmycin A3; tiacumicin B; X-ray analysis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Serra, S.; Malpezzi, L.; Bedeschi, A.; Fuganti, C.; Fonte, P. Final Demonstration of the Co-Identity of Lipiarmycin A3 and Tiacumicin B (Fidaxomicin) through Single Crystal X-ray Analysis. Antibiotics 2017, 6, 7.

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