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Total synthesis of cyclotheonamide C by use of an alpha-keto cyanophosphorane methodology for peptide assembly

Year: 2008

Type: article

Abstract: The total synthesis of cyclotheonamide C (3), a macrocyclic pentapeptide incorporating an alpha-keto homoarginine (k-Arg) and a vinylogous dehydrotyrosine (V-deltaTyr) unit, has been achieved. For comparison of macrocyclisation feasibility, two linear pentapeptides bearing free ketone functions at the k-Arg units were prepared, by use of tandem oxidation/coupling reactions on alpha-keto cyanophosphorane precursors as the key processes for pentapeptide elaboration. Successful activation and coupling at the pentapeptide V-deltaTyr C terminus led to the target molecule core, and thus provided a short total synthesis of the target compound

Source: HAL

Authors: Roche, Stéphane, Faure, Sophie, El Blidi, Lahssen, Aitken, D.J.

Institution: Institut de Chimie Moléculaire et des Matériaux d'Orsay

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

OpenAlex ID: W4206883256

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