A structural model of the ferrichrome type siderophore: chiral preference induced by intramolecular hydrogen bonding networks in ferric trihydroxamateElectronic supplementary information (ESI) available: UV-vis and CD spectra of 1 and details of the determination of the absolute configuration and the space group of 1 are deposited as supporting information. See http://www.rsc.org/suppdata/cc/b1/b100306m/

Abstract

Tris{2-[(N-acetyl-N-hydroxy)-D -alanylamino]ethyl}amine (R-TAAE) has been synthesized as a chiral trihydroxamate artificial siderophore with hydrogen bonding networks, whose crystal structure of the iron(III) complex revealed Λ configuration induced by interstrand hydrogen bonding networks and steric repulsion by optically active amino acid residues.