Coordination features of difunctionalized β-cyclodextrins with carnosine:: ESI-MS and spectroscopic investigations on 6A,6D-di-(β-alanyl-L-histidine)-6A,6D-dideoxy-β-cyclodextrin and 6A,6C-di-(β-alanyl-L-histidine)-6A,6C-dideoxy-β-cyclodextrin and their copper(II) complexes
Coordination features of difunctionalized β-cyclodextrins with carnosine:: ESI-MS and spectroscopic investigations on 6A,6D-di-(β-alanyl-L-histidine)-6A,6D-dideoxy-β-cyclodextrin and 6A,6C-di-(β-alanyl-L-histidine)-6A,6C-dideoxy-β-cyclodextrin and their copper(II) complexes
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DOI：
10.1016/j.jinorgbio.2003.10.015
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发表时间：
2004-02-01
影响因子：
3.9
通讯作者：
Vecchio, G
中科院分区：
文献类型：
--
作者：
Mineo, P;Vitalini, D;Vecchio, G
报道了两种以肌肽（β-丙氨酰-L-组氨酸）为氨基单元的β-环糊精（β-CD）6A，6C-（β-丙氨酰-L-组氨酸）-6A，6C-双脱氧-β-环糊精（ACCDAH）和6A，6D-（β-丙氨酰-L-组氨酸）-6A，6D-双脱氧-β-环糊精（ADCDAH）的合成与表征。NMR和C.D.配体的数据表明二肽链与β-CD的上边缘和空腔的不同相互作用。类似地，光谱和电喷雾电离质谱数据显示由两个区域异构体形成的不同的铜（II）络合物物种。肌肽-环糊精衍生物以头对尾方式结合铜离子的能力在两个肌肽部分相邻的ACCDAH的情况下诱导形成寡聚物种类（高达六聚体），而在ADCDAH的情况下，两个ADCDAH分子的肽链之间的相互作用允许几乎排他性地形成铜辅助的自组装二聚物种类。(C)2003年爱思唯尔公司All rights reserved.
The synthesis and characterization of two beta-cyclodextrins (beta-CD) functionalized with two units of carnosine (beta-alanyl-L-histidine) through the amino group, 6A,6C-(beta-alanyl-L-histidine)-6A,6C-dideoxy-beta-cyclodextrin (ACCDAH) and 6A,6D-(beta-alanyl-L-histidine)-6A,6D-dideoxy-beta-cyclodextrin (ADCDAH), are reported. NMR and C.D. data of the ligands indicate a different interaction of dipeptide chains with upper rim and cavity of beta-CD. Analogously, spectroscopic and electrospray ionization mass spectrometry data show different copper(II) complex species formed by the two regioisomers. The ability of carnosine-cyclodextrin derivatives to bind copper ions in a head-to-tail fashion induces the formation of oligomeric species (up to hexamers) in the case of ACCDAH, where the two carnosine moieties are adjacent, while in the ADCDAH case the mutual interaction between the peptidic chains of two ADCDAH molecules allows the almost exclusive formation of a copper-assisted self-assembled dimeric species. (C) 2003 Elsevier Inc. All rights reserved.