N-Carboxyanhydride-Mediated Fatty Acylation of Amino Acids and Peptides for Functionalization of Protocell Membranes,Journal of the American Chemical Society

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N-Carboxyanhydride-Mediated Fatty Acylation of Amino Acids and Peptides for Functionalization of Protocell Membranes
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2016-12-13 , DOI: 10.1021/jacs.6b08801
Enver Cagri Izgu _{1,

2} , Anders Björkbom _{1,

2,

3} , Neha P. Kamat _{1,

2} , Victor S. Lelyveld _{1,

2} , Weicheng Zhang _{1,

2,

4} , Tony Z. Jia _{1,

2,

4} , Jack W. Szostak _{1,

2,

4}

Affiliation

Early protocells are likely to have arisen from the self-assembly of RNA, peptide, and lipid molecules that were generated and concentrated within geologically favorable environments on the early Earth. The reactivity of these components in a prebiotic environment that supplied sources of chemical energy could have produced additional species with properties favorable to the emergence of protocells. The geochemically plausible activation of amino acids by carbonyl sulfide has been shown to generate short peptides via the formation of cyclic amino acid N-carboxyanhydrides (NCAs). Here, we show that the polymerization of valine-NCA in the presence of fatty acids yields acylated amino acids and peptides via a mixed anhydride intermediate. Notably, Nα-oleoylarginine, a product of the reaction between arginine and oleic acid in the presence of valine-NCA, partitions spontaneously into vesicle membranes and mediates the association of RNA with the vesicles. Our results suggest a potential mechanism by which activated amino acids could diversify the chemical functionality of fatty acid membranes and colocalize RNA with vesicles during the formation of early protocells.

中文翻译：

N-羧酸酐介导的氨基酸和肽的脂肪酰化用于原始细胞膜的功能化

早期的原始细胞很可能是由 RNA、肽和脂质分子的自组装产生的，这些分子在地球早期的地质有利环境中生成和集中。这些成分在提供化学能源的益生元环境中的反应性可能会产生具有有利于原始细胞出现的特性的其他物种。羰基硫对氨基酸的地球化学上合理的活化已被证明通过形成环状氨基酸 N-羧酸酐 (NCA) 产生短肽。在这里，我们表明缬氨酸-NCA 在脂肪酸存在下的聚合通过混合酸酐中间体产生酰化氨基酸和肽。值得注意的是，Nα-油酰精氨酸，在缬氨酸-NCA 存在下，精氨酸和油酸反应的产物，自发地进入囊泡膜并介导 RNA 与囊泡的结合。我们的结果表明了一种潜在的机制，通过该机制，活化的氨基酸可以使脂肪酸膜的化学功能多样化，并在早期原始细胞的形成过程中将 RNA 与囊泡共定位。

更新日期：2016-12-13

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