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Title: Synthesis and functional analysis of deferriferrichrysin derivatives: Application to colorimetric pH indicators.
Authors: Kobayashi, Yuka
Oishi, Shinya  kyouindb  KAKEN_id
Kobayashi, Kazuya
Ohno, Hiroaki  kyouindb  KAKEN_id
Tsutsumi, Hiroko
Hata, Yoji
Fujii, Nobutaka  KAKEN_id
Author's alias: 大石, 真也
Keywords: Deferriferrichrysin
Ferrichrome peptide
Hydroxamate
Iron complex
Siderophore
Issue Date: 15-Jul-2013
Publisher: Elsevier B.V.
Journal title: Bioorganic & medicinal chemistry
Volume: 21
Issue: 14
Start page: 4296
End page: 4300
Abstract: Deferriferrichrysin belongs to the siderophore peptide family which are Fe(III)-coordinating cyclic peptides. The common structure of this family is three consecutive hydroxamate moieties, such as N(δ)-acetyl-N(δ)-hydroxy-l-ornithine (Aho). We have designed two deferriferrichrysin derivatives where three Aho residues were arranged as: cyclo(-Aho-Gly-Aho-Gly-Aho-Gly-) and cyclo(-Aho-Ser-Aho-Ser-Aho-Ser-). Comparative evaluation of the physicochemical properties of their Fe(III) complexes revealed that naturally occurring deferriferrichrysin formed a more stable Fe(III) complex when compared with the two derivatives. This result shows that three consecutive Aho residues are indispensable for high affinity Fe(III) binding by deferriferrichrysin. Of note, the observed pH-dependent chromogenic response of the Fe(III) complexes of the derivatives suggests that these two derivatives should function as sensitive pH indicators in acidic environments.
Rights: © 2013 Elsevier B.V.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/176374
DOI(Published Version): 10.1016/j.bmc.2013.04.078
PubMed ID: 23721918
Appears in Collections:Journal Articles

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