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Paper | Regular issue | Vol 55, No. 11, 2001, pp.2171-2187
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9338
■ 3-Hydroxy-4(1H)-pyridinone-containing Linear and Cyclic Hexapeptides and Their Iron(III) Complexes —Synthesis, Property, and the Growth-Promotion Activity —

Akira Katoh,* Yasushi Hikita, Manabu Harata, Junko Ohkanda, Taro Tsubomura, Akon Higuchi, Ryota Saito, and Kazuo Harada

*Faculty of Engineering, Seikei University, Musashino, Tokyo 180-8633, Japan

Abstract

Linear and cyclic hexapeptides composed of ε-(3-hydroxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucine and glycine or β-alanine residue have been successfully synthesized. These hexapeptides formed 1:1 iron(III) complexes at neutral pH region. Glycine linear (8a)- and β-alanine cyclic hexa-peptide (10)-iron(III) complexes predominantly existed in Δ-configuration, while β-alanine linear hexapeptide (8b)-iron(III) complex existed in Λ-one. The relative stability constants of 8a, 8b, and 10-iron(III) complexes were estimated to be 31.6, 33.4, and 31.7, respectively. From iron(III) removal from human transferrin, linear hexapeptides (8a,b) were found to efficiently remove iron(III) compared with desferrioxamine B. The growth-promotion activity was also discussed.