Homochiral oligomerization of L-histidine in the presence of liposome membranes

Takaaki Ishigami, Yoshinori Kaneko, Keishi Suga, Yukihiro Okamoto, Hiroshi Umakoshi

研究成果: Article査読

4 被引用数 (Scopus)

抄録

We report about a novel method for the homochiral oligomerization of l-amino acids in the presence of liposomes. For this homochiral oligomerization, we took advantage of the superior properties of liposomes as chiral adsorbent, concentrator of reacting molecules, and as effective reaction medium. Indeed, liposomes composed of l-phospholipids could enantioselectively bind and concentrate only l-histidine (l-His) on the liposome membrane, and not D-His, which was confirmed by UV measurements. Furthermore, we demonstrate that the liposomes enabled effective oligomerization of l-His on or in the liposome membrane, while the oligomerization of d-His in the liposome system—or in absence of liposomes—was less efficient. The experimental findings are supported by logP value calculations. These calculations indicate that activated intermediates locate in the center of the bilayer where they are protected from hydrolysis due to the hydrophobic environment of the liposome membrane. Therefore, the use of liposomes from l-phospholipids enables homochiral oligomerization and more efficient oligomerization of l-amino acids as compared to d-amino acids. Thus, our developed method could be used for the synthesis of homochiral polymers from racemic mixtures of monomers and may contribute to the understanding of prebiotic biopolymer formation.

本文言語English
ページ(範囲)3649-3653
ページ数5
ジャーナルColloid and Polymer Science
293
12
DOI
出版ステータスPublished - 2015 12 1
外部発表はい

ASJC Scopus subject areas

  • 物理化学および理論化学
  • ポリマーおよびプラスチック
  • コロイド化学および表面化学
  • 材料化学

フィンガープリント

「Homochiral oligomerization of L-histidine in the presence of liposome membranes」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル