Talarolide A, a cyclic heptapeptide hydroxamate from an Australian marine tunicate-associated fungus, Talaromyces sp. (CMB-TU011)

Dewapriya, Pradeep, Prasad, Pritesh, Damodar, Rakesh, Salim, Angela A. and Capon, Robert J. (2017) Talarolide A, a cyclic heptapeptide hydroxamate from an Australian marine tunicate-associated fungus, Talaromyces sp. (CMB-TU011). Organic Letters, 19 8: 2046-2049. doi:10.1021/acs.orglett.7b00638


Author Dewapriya, Pradeep
Prasad, Pritesh
Damodar, Rakesh
Salim, Angela A.
Capon, Robert J.
Title Talarolide A, a cyclic heptapeptide hydroxamate from an Australian marine tunicate-associated fungus, Talaromyces sp. (CMB-TU011)
Formatted title
Talarolide A, a cyclic heptapeptide hydroxamate from an Australian marine tunicate-associated fungus, Talaromyces sp. (CMB-TU011)
Journal name Organic Letters   Check publisher's open access policy
ISSN 1523-7052
1523-7060
Publication date 2017-04-21
Year available 2017
Sub-type Article (original research)
DOI 10.1021/acs.orglett.7b00638
Open Access Status Not yet assessed
Volume 19
Issue 8
Start page 2046
End page 2049
Total pages 4
Place of publication Washington, DC, United States
Publisher American Chemical Society
Language eng
Subject 1303 Biochemistry
1606 Physical and Theoretical Chemistry
1605 Organic Chemistry
Abstract A miniaturized 24-well plate microbioreactor approach was used to explore secondary metabolite media dependence in an Australian marine tunicate-associated fungus, Talaromyces sp. (CMB TU011). Detailed chemical investigations of an antifungal M1-saline cultivation yielded talarolide A (1), only the second reported natural cyclic peptide hydroxamate, and the first from a fungus. The antifungal properties of the M1-saline extract were attributed to the known diterpene glycoside sordarin (2). Structure elucidation of 1 and 2 was achieved by detailed spectroscopic analysis, with amino acid configurations in 1 assigned by the C and C Marfey's methods, and l-Ala and d-Ala regiochemistry by the recently reported 2D C Marfey's method.
Formatted abstract
A miniaturized 24-well plate microbioreactor approach was used to explore secondary metabolite media dependence in an Australian marine tunicate-associated fungus, Talaromyces sp. (CMB TU011). Detailed chemical investigations of an antifungal M1-saline cultivation yielded talarolide A (1), only the second reported natural cyclic peptide hydroxamate, and the first from a fungus. The antifungal properties of the M1-saline extract were attributed to the known diterpene glycoside sordarin (2). Structure elucidation of 1 and 2 was achieved by detailed spectroscopic analysis, with amino acid configurations in 1 assigned by the C3 and C18 Marfey’s methods, and l-Ala and d-Ala regiochemistry by the recently reported 2D C3 Marfey’s method.
Keyword Chemistry, Organic
Chemistry
Q-Index Code C1
Q-Index Status Provisional Code
Grant ID LP120100088
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: HERDC Pre-Audit
Institute for Molecular Bioscience - Publications
 
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