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Synthesis 2016; 48(23): 4149-4154
DOI: 10.1055/s-0035-1560564
DOI: 10.1055/s-0035-1560564
paper
Synthesis of Erythrochelin: A Hydroxamate-Type Siderophore from Saccharopolyspora erythraea
Further Information
Publication History
Received: 03 July 2016
Accepted after revision: 19 July 2016
Publication Date:
24 August 2016 (online)
Abstract
Erythrochelin, a hydroxamate-type siderophore produced by Saccharopolyspora erythraea, is synthesized for the first time. A key building block of erythrochelin containing the 2,5-diketopiperazine ring is prepared by intramolecular cyclization of the corresponding dipeptide precursor derived from two kinds of protected δ-N-hydroxy-l-ornithines. Consecutive condensation of the building block with protected d-serine and protected δ-N-hydroxy-d-ornithine, followed by deprotection, furnishes erythrochelin.
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