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Short Paper | Special issue | Vol 101, No. 1, 2020, pp.347-356
Published online, 30th August, 2019
DOI: 10.3987/COM-19-S(F)27
Synthesis of Three Stereoisomers of Erythrochelin, a Hydroxamate-Type Tetrapeptide Siderophore from Saccharopolyspora erythraea

Michiyasu Nakao, Ayumu Adachi, Syuji Kitaike, and Shigeki Sano*

*Graduate School of Pharmaceutical Sciences, Tokushima University, 1-78 Sho-machi, Tokushima 770-8505, Japan


Details of the synthesis of three stereoisomers of erythrochelin, a hydroxamate-type tetrapeptide siderophore produced by Saccharopolyspora erythraea, were described. Both enantiomers of protected δ-N-hydroxyornithine were used as key intermediates in the synthesis of stereoisomers of erythrochelin containing a (3S,6S)-3,6-disubstituted-2,5-diketopiperazine ring. From comparisons of 1H and 13C NMR spectra, neither of stereoisomers provided a match for the erythrochelin spectral data, and the absolute configuration of erythrochelin was unambiguously reconfirmed to be (R,R,S,S).