Isolation and structure elucidation of thiazomycin- a potent thiazolyl peptide antibiotic from Amycolatopsis fastidiosa
- PMID: 17917238
- DOI: 10.1038/ja.2007.70
Isolation and structure elucidation of thiazomycin- a potent thiazolyl peptide antibiotic from Amycolatopsis fastidiosa
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 articles
-
Thiazomycins, thiazolyl peptide antibiotics from Amycolatopsis fastidiosa.J Nat Prod. 2009 May 22;72(5):841-7. doi: 10.1021/np800783b. J Nat Prod. 2009. PMID: 19334707
-
Isolation, structure, and antibacterial activity of thiazomycin A, a potent thiazolyl peptide antibiotic from Amycolatopsis fastidiosa.Bioorg Med Chem. 2008 Oct 1;16(19):8818-23. doi: 10.1016/j.bmc.2008.08.079. Epub 2008 Sep 6. Bioorg Med Chem. 2008. PMID: 18804380
-
Antibacterial evaluations of thiazomycin- a potent thiazolyl peptide antibiotic from Amycolatopsis fastidiosa.J Antibiot (Tokyo). 2007 Sep;60(9):565-71. doi: 10.1038/ja.2007.71. J Antibiot (Tokyo). 2007. PMID: 17917239
-
Nocathiacin, Thiazomycin, and Polar Analogs Are Highly Effective Agents against Toxigenic Clostridioides difficile.J Nat Prod. 2022 Apr 22;85(4):1141-1146. doi: 10.1021/acs.jnatprod.2c00093. Epub 2022 Apr 5. J Nat Prod. 2022. PMID: 35380836 Review.
-
From amino acids to heteroaromatics--thiopeptide antibiotics, nature's heterocyclic peptides.Angew Chem Int Ed Engl. 2007;46(42):7930-54. doi: 10.1002/anie.200700728. Angew Chem Int Ed Engl. 2007. PMID: 17854013 Review.
Cited by
-
Secondary Metabolites of the Genus Amycolatopsis: Structures, Bioactivities and Biosynthesis.Molecules. 2021 Mar 26;26(7):1884. doi: 10.3390/molecules26071884. Molecules. 2021. PMID: 33810439 Free PMC article. Review.
-
Current approaches to exploit actinomycetes as a source of novel natural products.J Ind Microbiol Biotechnol. 2011 Mar;38(3):375-89. doi: 10.1007/s10295-010-0882-7. Epub 2010 Oct 8. J Ind Microbiol Biotechnol. 2011. PMID: 20931260 Review.
-
Thiopeptide antibiotics: retrospective and recent advances.Mar Drugs. 2014 Jan 17;12(1):317-51. doi: 10.3390/md12010317. Mar Drugs. 2014. PMID: 24445304 Free PMC article. Review.
-
Bioactive heterocycles containing endocyclic N-hydroxy groups.Eur J Med Chem. 2015 Jun 5;97:505-24. doi: 10.1016/j.ejmech.2014.11.031. Epub 2014 Nov 18. Eur J Med Chem. 2015. PMID: 25466924 Free PMC article. Review.
-
A comprehensive review of glycosylated bacterial natural products.Chem Soc Rev. 2015 Nov 7;44(21):7591-697. doi: 10.1039/c4cs00426d. Chem Soc Rev. 2015. PMID: 25735878 Free PMC article. Review.
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
Medical
