Symplocin A, a linear peptide from the Bahamian cyanobacterium Symploca sp. Configurational analysis of N,N-dimethylamino acids by chiral-phase HPLC of naphthacyl esters.

Journal of Natural Products
Tadeusz F MolinskiBrandon I Morinaka

Abstract

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 (IC(50) 300 pM).

References

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Citations

Aug 8, 2013·The Journal of Antibiotics·Timothy R RamadharJon Clardy
Jun 25, 2014·Journal of Natural Products·Yi SunShigeki Matsunaga
Jan 13, 2015·Natural Product Reports·Lilibeth A Salvador-Reyes, Hendrik Luesch
Dec 7, 2017·Frontiers in Pharmacology·Shivankar AgrawalSunil K Deshmukh
Jun 4, 2019·Marine Drugs·Justine DemayBenjamin Marie
Jan 7, 2014·Natural Product Reports·John W BluntMichèle R Prinsep
Jun 11, 2020·Natural Product Reports·Fatma H Al-Awadhi, Hendrik Luesch
Jun 1, 2017·Organic Chemistry Frontiers : an International Journal of Organic Chemistry·Lu-Ping ShaoGuo-Qiang Lin
May 14, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lik Tong Tan, Ma Yadanar Phyo
Mar 5, 2021·Pharmacological Research : the Official Journal of the Italian Pharmacological Society·Abdur RaufKannan Rr Rengasamy
Mar 5, 2014·Journal of Natural Products·Emily MeversWilliam H Gerwick

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