Syntheses of both the putative and revised structures of aeruginosin EI461 bearing a new bicyclic alpha-amino acid.
[structure: see text] The putative structure of the naturally occurring aquatic peptide aeruginosin EI461 has been prepared from d-tyrosine. A corrected structure for aeruginosin EI461 is proposed, and the structure is proven by synthesis, which was accomplished using the new alpha-amino acid (2S,3aR,6R,7aR)-6-hydroxy-2-carboxyoctahydroindole, prepared from l-tyrosine. Succesive couplings of the dipeptide d-Leu-3a,7a-diepi-l-Choi with l-Hpla and NH(4)OH and a deprotection step gave aeruginosin EI461.
Valls
Nativitat
N
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain.
Vallribera
Mercè
M
Carmeli
Shmuel
S
Bonjoch
Josep
J
D004151:Dipeptides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis*; D011480:Protease Inhibitors / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014443:Tyrosine / Q000737:chemistry
D004151:Dipeptides; D009842:Oligopeptides; D011480:Protease Inhibitors; C465430:aeruginosin EI461; D014443:Tyrosine