Homophymamide A, Heterodetic Cyclic Tetrapeptide from a Homophymia sp. Marine Sponge: A Cautionary Note on Configurational Assignment of Peptides That Contain a Ureido Linkage

J Nat Prod. 2021 Jun 25;84(6):1848-1853. doi: 10.1021/acs.jnatprod.1c00336. Epub 2021 Jun 3.

Abstract

A previously unreported heterodetic cyclic peptide, homophymamide A (1), was isolated from a Homophymia sp. marine sponge. The structure of homophymamide A was determined to be a lower homologue of anabaenopeptins by spectroscopic analysis, chemical degradation, and chemical synthesis. Analysis of the acidic hydrolysate showed that the racemization of Lys took place, leading us to pose a cautionary note on the configurational assignment of peptides that contain a ureido bond.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Japan
  • Molecular Structure
  • Peptides, Cyclic / chemistry*
  • Porifera / chemistry*

Substances

  • Peptides, Cyclic