4′-Aminomethyl-2,2′-bipyridyl-4-carboxylic Acid (Abc) and Related Derivatives: Novel Bipyridine Amino Acids for the Solid-Phase Incorporation of a Metal Coordination Site Within a Peptide Backbone
作者:Barney M. Bishop、Dewey G. McCafferty、Bruce W. Erickson
DOI:10.1016/s0040-4020(00)00367-7
日期:2000.6
The novel bipyridyl amino acid, 4′-aminomethyl-2,2′-bipyridyl-4-carboxylic acid (Abc), and related Boc- and Fmoc-protected derivatives were synthesized to provide high-affinity bidentate metal-binding amino acid modules for the solid-phase peptide synthesis (SPPS) of metallopeptides. Since the bipyridyl group of Abc is inserted into the peptide mainchain and not in the sidechain, its presence in a
合成了新颖的联吡啶基氨基酸,4'-氨基甲基-2,2'-联吡啶基-4 - c羟基丁酸(Abc)以及相关的Boc和Fmoc保护的衍生物,以提供高亲和力的双齿金属结合氨基酸模块用于金属肽的固相肽合成(SPPS)。由于Abc的联吡啶基是插入到肽主链中而不是在侧链中,所以它在肽中的存在应对骨架几何结构赋予独特的构象约束,从而影响局部二级结构。为了证明其对SPPS的适应性和金属络合能力,将Abc掺入六肽Ac-Ala- Abc -Ahx-Ahx- Abc -Gly-NH 2(肽Aha; (其中Ahx =氨基己酸),然后用作四齿配体以八面体配位和不对称地封装钌(II)离子,从而创建了一种新型的肽笼罩式氧化还原活性金属络合物。