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Talaropeptides A-D: Structure and Biosynthesis of Extensively N-methylated Linear Peptides From an Australian Marine Tunicate-Derived Talaromyces sp.


ABSTRACT: An Australian marine tunicate-derived fungus, Talaromyces sp. CMB-TU011 was subjected to a program of analytical microbioreactor (MATRIX) cultivations, supported by UHPLC-QTOF profiling, to reveal conditions for producing a new class of extensively N-methylated 11-12 residue linear peptides, talaropeptides A-D (2-5). The structures for 2-5, inclusive of absolute configurations, were determined by a combination of detailed spectroscopic and chemical (e.g., C3 and C18 Marfey's) analyses. We report on the biological properties of 2-5, including plasma stability, as well as antibacterial, antifungal and cell cytotoxicity. The talaropeptide mega non-ribosomal peptide synthetase (NRPS) is described, as second only in size to that for the fungus-derived immunosuppressant cyclosporine (an 11-residue extensively N-methylated cyclic peptide).

SUBMITTER: Dewapriya P 

PROVIDER: S-EPMC6131563 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Talaropeptides A-D: Structure and Biosynthesis of Extensively <i>N</i>-methylated Linear Peptides From an Australian Marine Tunicate-Derived <i>Talaromyces</i> sp.

Dewapriya Pradeep P   Khalil Zeinab G ZG   Prasad Pritesh P   Salim Angela A AA   Cruz-Morales Pablo P   Marcellin Esteban E   Capon Robert J RJ  

Frontiers in chemistry 20180904


An Australian marine tunicate-derived fungus, <i>Talaromyces</i> sp. CMB-TU011 was subjected to a program of analytical microbioreactor (MATRIX) cultivations, supported by UHPLC-QTOF profiling, to reveal conditions for producing a new class of extensively <i>N</i>-methylated 11-12 residue linear peptides, talaropeptides A-D (<b>2</b>-<b>5</b>). The structures for <b>2</b>-<b>5</b>, inclusive of absolute configurations, were determined by a combination of detailed spectroscopic and chemical (e.g.  ...[more]

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