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Syntheses of both the putative and revised structures of aeruginosin EI461 bearing a new bicyclic alpha-amino acid
Authors:Valls Nativitat  Vallribera Mercè  Carmeli Shmuel  Bonjoch Josep
Institution:Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain.
Abstract: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.
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