More Peptides and Other Diverse Constituents of the Marine Mollusk Philinopsis speciosa

Youichi Nakao, Wesley Y. Yoshida, Christina M. Szabo, Bill J. Baker, Paul J. Scheuer

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

In addition to five new depsipeptides related to kulolide-1 (1), further examination of the mollusk Philinopsis speciosa has yielded a linear peptide, pupukeamide (14), and an unprecedented macrolide, tolytoxin-23-acetate (7). Chemical makeup suggested that the compounds originate from blue-green algae and are transmitted via herbivorous mollusks to P. speciosa. This could be verified by laboratory experiment. The structures were determined largely by spectroscopic techniques and the stereochemistry by hydrolysis of the peptides followed by chiral chromatography.

Original languageEnglish
Pages (from-to)3272-3280
Number of pages9
JournalJournal of Organic Chemistry
Volume63
Issue number10
Publication statusPublished - 1998 May 15
Externally publishedYes

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Depsipeptides
Peptides
Stereochemistry
Macrolides
Chromatography
Hydrolysis
Acetates
Experiments
tolytoxin
Cyanobacteria

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Nakao, Y., Yoshida, W. Y., Szabo, C. M., Baker, B. J., & Scheuer, P. J. (1998). More Peptides and Other Diverse Constituents of the Marine Mollusk Philinopsis speciosa. Journal of Organic Chemistry, 63(10), 3272-3280.

More Peptides and Other Diverse Constituents of the Marine Mollusk Philinopsis speciosa. / Nakao, Youichi; Yoshida, Wesley Y.; Szabo, Christina M.; Baker, Bill J.; Scheuer, Paul J.

In: Journal of Organic Chemistry, Vol. 63, No. 10, 15.05.1998, p. 3272-3280.

Research output: Contribution to journalArticle

Nakao, Y, Yoshida, WY, Szabo, CM, Baker, BJ & Scheuer, PJ 1998, 'More Peptides and Other Diverse Constituents of the Marine Mollusk Philinopsis speciosa', Journal of Organic Chemistry, vol. 63, no. 10, pp. 3272-3280.
Nakao, Youichi ; Yoshida, Wesley Y. ; Szabo, Christina M. ; Baker, Bill J. ; Scheuer, Paul J. / More Peptides and Other Diverse Constituents of the Marine Mollusk Philinopsis speciosa. In: Journal of Organic Chemistry. 1998 ; Vol. 63, No. 10. pp. 3272-3280.
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