期刊
JOURNAL OF NATURAL PRODUCTS
卷 75, 期 3, 页码 425-431出版社
AMER CHEMICAL SOC
DOI: 10.1021/np200861n
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资金
- NSF (CRIF) [CHE0741968]
- NIH [AI039987]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0741968] Funding Source: National Science Foundation
The absolute stereostructures of the components of symplocin A (3), a new N,N-dimethyl-terminated peptide from the Bahamian cyanobacterium Symploca sp., were assigned from spectroscopic analysis, including MS, 2D NMR, and Marfey's analysis. The complete absolute configuration of symplocin A, including the unexpected D-configurations of the terminal N,N-dimethylisoleucine and valic acid residues, was assigned by chiral-phase HPLC of the corresponding 2-naphthacyl esters, a highly sensitive, complementary strategy for assignment of N-blocked peptide residues where Marfey's method is ineffectual or other methods fall short. Symplocin A exhibited potent activity as an inhibitor of cathepsin E (IC50 300 pM).
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