Syntheses of both the putative and revised structures of aeruginosin EI461 bearing a new bicyclic α-amino acid

Nativitat Valls; Mercè Vallribera; Shmuel Carmeli; Josep Bonjoch

doi:10.1021/ol0273250

Syntheses of both the putative and revised structures of aeruginosin EI461 bearing a new bicyclic α-amino acid

Nativitat Valls^*, Mercè Vallribera, Shmuel Carmeli, Josep Bonjoch

^*Corresponding author for this work

School of Chemistry

University of Barcelona

Research output: Contribution to journal › Article › peer-review

48 Scopus citations

Abstract

(Matrix presented) 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 α-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 NH₄OH and a deprotection step gave aeruginosin EI461.

Original language	English
Pages (from-to)	447-450
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	4
DOIs	https://doi.org/10.1021/ol0273250
State	Published - 20 Feb 2003

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abstract = "(Matrix presented) 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 α-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 NH4OH and a deprotection step gave aeruginosin EI461.",

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T1 - Syntheses of both the putative and revised structures of aeruginosin EI461 bearing a new bicyclic α-amino acid

AU - Valls, Nativitat

AU - Vallribera, Mercè

AU - Carmeli, Shmuel

AU - Bonjoch, Josep

PY - 2003/2/20

Y1 - 2003/2/20

N2 - (Matrix presented) 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 α-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 NH4OH and a deprotection step gave aeruginosin EI461.

AB - (Matrix presented) 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 α-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 NH4OH and a deprotection step gave aeruginosin EI461.

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Syntheses of both the putative and revised structures of aeruginosin EI461 bearing a new bicyclic α-amino acid

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