化学
二肽
测试表
肽
氨基酸
立体化学
拟肽
组合化学
折叠(DSP实现)
生物化学
电气工程
工程类
作者
Matthew P. Sarnowski,Kyle P. Pedretty,Nicole Giddings,H. Lee Woodcock,Juan R. Del Valle
标识
DOI:10.1016/j.bmc.2017.08.017
摘要
The stabilization of β-sheet secondary structure through peptide backbone modification represents an attractive approach to protein mimicry. Here, we present strategies toward stable β-hairpin folds based on peptide strand N-amination. Novel pyrazolidinone and tetrahydropyridazinone dipeptide constraints were introduced via on-resin Mitsunobu cyclization between α-hydrazino acid residues and a serine or homoserine side chain. Acyclic and cyclic N-amino peptide building blocks were then evaluated for their effect on β-hairpin stability in water using a GB1-derived model system. Our results demonstrate the strong β-sheet stabilizing effect of the peptide N-amino substituent, and provide useful insights into the impact of covalent dipeptide constraint on β-sheet folding.
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