Tawicyclamides A and B, new cyclic peptides from the Ascidian Lissoclinum patella: studies on the solution- and solid-state conformations

Autor:	Chris M. Ireland, Jon Clardy, Angela Y. Lee, Leonard A. McDonald, Mark P. Foster, Dennis R. Phillips
Rok vydání:	1992
Předmět:	chemistry.chemical_classification Stereochemistry Hydrogen bond Chemistry Intramolecular force Organic Chemistry Peptide bond Molecule Lissoclinum patella Tandem mass spectrometry Cyclic peptide Amino acid
Zdroj:	The Journal of Organic Chemistry. 57:4616-4624
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00043a017
Popis:	Two new cytotoxic cyclic peptides, tawicyclamides A and B (1-2), were isolatedfrom the ascidian Lissoclinum patella collected in the Philippine Islands and their structures determined byNMR spectroscopy, oxidation studies, and tandem mass spectrometry. Absolute configurations were determined by HPLC analysis of derivatized constituent amino acids obtained from acid hydrolysis. X-ray crystallography confirmed the structure of tawicyclamide B and showed that the compound assumes an unusual conformation facilitated by a cis-valine-proline amide bond and stabilized by an intramolecular hydrogen bond
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7eff0318d16d4fec75de9c2f85b2d6da https://doi.org/10.1021/jo00043a017 Zobrazit plný text záznamu