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ABSTRACT Thiazolyl peptides are a class of rigid macrocyclic compounds richly populated with thiazole rings. They are highly potent antibiotics but none have been advanced to clinic due to

poor aqueous solubility. Recent progress in this field prompted a reinvestigation leading to the isolation of a new thiazolyl peptide, thiazomycin, a congener of nocathiacins. Thiazomycin

possesses an oxazolidine ring as part of the amino-sugar moiety in contrast to the dimethyl amino group present in nocathiacin I. The presence of the oxazolidine ring provides additional

opportunities for chemical modifications that are not possible with other nocathiacins. Thiazomycin is extremely potent against Gram-positive bacteria both _in vitro_ and _in vivo_. The

titer of thiazomycin in the fermentation broth was very low compared to the nocathiacins I and III. The lower titer together with its sandwiched order of elution presented significant

challenges in large scale purification of thiazomycin. This problem was resolved by the development of an innovative preferential protonation based one- and/or two-step chromatographic

method, which was used for pilot plant scale purifications of thiazomycin. The isolation and structure elucidation of thiazomycin is herein described. SIMILAR CONTENT BEING VIEWED BY OTHERS

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scale. _Biotechnol Bioeng_ 79: 628–640 ( 2002) Article  CAS  PubMed  Google Scholar  Download references AUTHOR INFORMATION Author notes * John F Barrett: Deceased AUTHORS AND AFFILIATIONS *

Merck Research Laboratories, Rahway, New Jersey, USA Hiranthi Jayasuriya, Kithsiri Herath, John G Ondeyka, Chaowei Zhang, Deborah L Zink, Mark Brower, Francis P Gailliot, Joyce Greene, 

Gwyneth Birdsall, Jayashree Venugopal, Misti Ushio, Bruce Burgess, Greg Russotti, Andre Walker, Michelle Hesse, Anna Seeley, Beth Junker, Neal Connors, Kun Liu, Prakash Masurekar & Sheo

B Singh * Centro de Investigación Básica, Merck Sharp & Dohme de España, S. A. Josefa Valcárcel 38, Madrid, 28027, Spain Oscar Salazar & Olga Genilloud Authors * Hiranthi Jayasuriya

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AUTHOR Correspondence to Sheo B Singh. RIGHTS AND PERMISSIONS Reprints and permissions ABOUT THIS ARTICLE CITE THIS ARTICLE Jayasuriya, H., Herath, K., Ondeyka, J. _et al._ Isolation and

Structure Elucidation of Thiazomycin. _J Antibiot_ 60, 554–564 (2007). https://doi.org/10.1038/ja.2007.70 Download citation * Received: 02 June 2007 * Accepted: 17 August 2007 * Issue Date:

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protein synthesis inhibitors * natural products