PROTEO, CCVC, Département de Chimie, Université Laval, 1045 Avenue de la Médecine, Québec, Québec, G1V 0A6, Canada.
Chembiochem. 2019 Jul 15;20(14):1817-1826. doi: 10.1002/cbic.201900082. Epub 2019 Jun 24.
The local hydrophobicity of an amino acid residue in a peptide sequence can be determined by measuring the hydrophobicity index (φ ) by reversed-phase (RP) HPLC. Herein, the impact on the local hydrophobicity of the replacement of an amide by a monofluoroalkene unit in short peptides is discussed. Monofluoroalkene-containing dipeptides and tripeptides were synthesized, as well as their natural parent compounds, and the hydrophobicity indexes of these short peptides and peptidomimetics were determined. Comparison between the natural parent peptides and their alkene-containing analogues was made, and the dependence of the peptidomimetic analogues' behaviour on the pH and the solvent was studied. It was found that the presence of a monofluoroalkene unit enhanced a peptide's hydrophobicity.
可以通过反相（RP）HPLC 测量疏水性指数（φ）来确定肽序列中氨基酸残基的局部疏水性。本文讨论了在短肽中用单氟烯烃单元取代酰胺对局部疏水性的影响。合成了含单氟烯烃的二肽和三肽及其天然母体化合物，并测定了这些短肽和肽类似物的疏水性指数。比较了天然母体肽与其含烯类似物的性质，并研究了肽类似物行为对 pH 和溶剂的依赖性。结果表明，单氟烯烃单元的存在增强了肽的疏水性。
