Medusamide A, a Panamanian cyanobacterial depsipeptide with multiple beta-amino acids

TitleMedusamide A, a Panamanian cyanobacterial depsipeptide with multiple beta-amino acids
Publication TypeJournal Article
Year of Publication2016
AuthorsFenner AM, Engene N, Spadafora C., Gerwick WH, Balunas M.J
JournalOrganic Letters
Volume18
Pagination352-355
Date Published2016/02
Type of ArticleArticle
ISBN Number1523-7060
Accession NumberWOS:000369771800003
Keywordsbiosynthesis; configuration; lyngbya-majuscula; marine natural-products; organisms; peptide; polyketide synthase; synthetase; system; unit
Abstract

From a collection of marine cyanobacteria made in the Coiba National Park along the Pacific coast of the Republic of Panama a novel cyclic depsipeptide, given the trivial name medusamide A, has been isolated and fully characterized. Medusamide A contains four contiguous beta-amino acid (2R,3R)-3-amino-2-methylhexanoic acid (Amha) residues. This is the first report of multiple Amha residues and contiguous beta-amino acid residues within a single cyclic peptide-type natural product. Stereochemical assignment of the Amha residues was completed following the synthesis of reference standards for this beta-amino acid and the subsequent derivatization with Marfey's reagent and LC-MS analysis.

DOI10.1021/acs.orglett.5b03110
Short TitleOrg. Lett.
Student Publication: 
No
Research Topics: