手性二茂铁色氨酸化合物[Fc-(CO-L-Trp-OMe)_2]的合成和结构表征(英文)

Synthesis and Structural Characterization of a Chirality Organization of Ferrocenoyl Peptide [Fc-(CO-L-Trp-OMe)_2]

由色氨酸甲酯和1,1′-二茂铁二羧酸合成了化合物1[Fc-(CO-L-Trp-OMe)2],并对化合物1在固体和溶液中的结构进行了表征。单晶结构表明,该化合物通过2个分子内氢键,形成了规则的手性构象。通过分子间的氢键,形成了二维网状结构。对化合物1的乙腈溶液进行了CD谱的测定,结果表明,该化合物在溶液中呈现P螺旋构象。1HNMR谱和FTIR谱也证实了该化合物在固体和溶液状态中都形成了含分子内氢键的构象。

The disubstituted ferrocenoyl peptide 1 [Fc-（CO-L-Trp-OMe）2] was prepared from ferrocenedicarboxylic acid （Fc（OH）2） and tryptophan methyl ester. The structure of 1 was studied in the solid state and in solution. The single-crystal structure shows that 1 displays a 1,2′-conformation and two intramolecular hydrogen bondings between CO （Trp） and NH （another Trp） of each peptide chain induce the chirality-organized structure. Additional intermolecular H-bonding in 1 allows the formation of a 2D net. CD spectra were recorded for 1 in MeCN. It clearly shows a P-helical arrangement of the ferrocene moiety. ^1H NMR spectroscopy in CDCl3 and FTIR spectroscopy in KBr also conform the ordered, intramolecular hydrogen bonded conformation in both solid and solution states.