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