Lobocyclamides A-C, lipopeptides from a cryptic cyanobacterial mat containing Lyngbya confervoides

John B. MacMillan, Michael A. Ernst-Russell, Jeffrey S. De Ropp, Tadeusz F. Molinski

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

The structures of lipopeptides lobocyclamides A (1), B (2), and C (3) were solved using a combination of mass spectrometry, 2D NMR spectroscopy, and degradative analysis. Lobocyclamides B and C are the first peptides reported with the unusual amino acid 4-hydroxythreonine and also incorporate the rare homologous long-chain β-amino acids 3-aminooctanoic acid and 3-aminodecanoic acid, respectively. The absolute configurations of the amino acid residues in each compound were assigned, after acid hydrolysis, by either direct chiral HPLC comparison with authentic standards or by prior derivatization by Marfey's method and reversed-phase HPLC. Both compounds exhibited moderate antifungal activity against a panel of Candida spp., including two fluconazole-resistant strains. When tested as a mixture, lobocyclamides A and B displayed synergistic in vitro antifungal activity, a phenomenon noted earlier for the related peptides laxaphycins A and B.

Original languageEnglish (US)
Pages (from-to)8210-8215
Number of pages6
JournalJournal of Organic Chemistry
Volume67
Issue number23
DOIs
StatePublished - Nov 15 2002

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Lipopeptides
Amino Acids
Acids
Peptides
Fluconazole
Candida
Nuclear magnetic resonance spectroscopy
Mass spectrometry
Hydrolysis
lobocyclamide A
lobocyclamide B

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Lobocyclamides A-C, lipopeptides from a cryptic cyanobacterial mat containing Lyngbya confervoides. / MacMillan, John B.; Ernst-Russell, Michael A.; De Ropp, Jeffrey S.; Molinski, Tadeusz F.

In: Journal of Organic Chemistry, Vol. 67, No. 23, 15.11.2002, p. 8210-8215.

Research output: Contribution to journalArticle

MacMillan, John B. ; Ernst-Russell, Michael A. ; De Ropp, Jeffrey S. ; Molinski, Tadeusz F. / Lobocyclamides A-C, lipopeptides from a cryptic cyanobacterial mat containing Lyngbya confervoides. In: Journal of Organic Chemistry. 2002 ; Vol. 67, No. 23. pp. 8210-8215.
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