The opposite effect of K+ and Na+ on the hydrolysis of linear and cyclic dipeptides

被引：16
作者：
Campbell, Thomas D. [1 ]
Hart, Clara A. [1 ]
Febrian, Rio [1 ]
Cheneler, Mark L. [1 ]
Bracher, Paul J. [1 ]
机构：
[1] St Louis Univ, Dept Chem, St Louis, MO 63103 USA
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 23期
基金：
美国国家科学基金会;
关键词：
Peptides; Potassium; Prebiotic chemistry; Origin of life; MEMBRANE BIOENERGETICS; PEPTIDE FORMATION; ORIGIN; LIFE; PROTEIN; RNA; HOFMEISTER; EVOLUTION; DESIGN; WATER;
D O I：
10.1016/j.tetlet.2018.04.073
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Potassium and sodium are generally considered inert 'spectator' ions for organic reactions. Here, we report rate constants for the acid-promoted hydrolysis of the seven dipeptides of glycine (G) and alanine (A) and an unexpected pattern in how these rates differ in the presence of K+ and Na+. The linear dipeptides hydrolyze 12-18% percent slower in the presence of KCl versus an equal concentration of NaCl, while the cyclic dipeptides hydrolyze 5-13% faster in the presence of KCl (all P-values < 0.025). We believe this is the first report of a general organic reaction-here, amide hydrolysis-for which some substrates react faster in the presence of K+ and others in Na+. The results offer a potential reason for life's mysterious universal selection of intracellular potassium over sodium. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2264 / 2267
页数：4
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