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9-ヒドロキシステアール酸の内生パルミチン酸エステルのステレオ化学と絶対構成の規制への関連性

Andrew T Nelson^1,2,3, Matthew J Kolar⁴, Qian Chu⁴

¹Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California-San Diego , 9500 Gilman Drive, La Jolla, California 92093-0934, United States.

Journal of the American Chemical Society

|March 29, 2017

まとめ

ステレオ化学は,ヒドロキシ脂肪酸 (FAHFA) の脂肪酸エステルにとって極めて重要です. この研究は,FAHFA代謝に影響を与えるステレオスペシフィックな生成と分解経路を持つ脂肪組織におけるR- 9- PAHSAが主たる形態であることを明らかにしています.

科学分野:

生物化学
リピドミクス
分子生物学

背景:

脂質は細胞構造,エネルギー,信号伝達に不可欠です.
ハイドロキシ脂肪酸の脂肪酸エステル (FAHFA) は,抗糖尿病および抗炎症性を持っています.
FAHFAに関する以前の研究では,レーセミック混合物が用いられ,ステレオ化学の役割は未探究であった.

研究の目的:

9-ヒドロキシステアール酸 (PAHSA) のエナティオメリックに純粋なR-およびS-パルミチン酸エステルを合成する.
9-PAHSAの立体同位体分離と定量化のための方法を開発する.
9-PAHSAの生物合成と分解のステレオ特異性を調査する.

主な方法:

エナンチオプアRとS-9-PAHSAの合成
立体同位体分離と定量化のための液体染色体質量測定法 (LC-MS) の開発.
PAHSAの生成と分解経路の生化学分析

主要な成果:

R- 9- PAHSAは,トランスゲンマウスの脂肪組織における主要なステレオ同位体として特定された.
R-9-PAHSAを生成する細胞系が好ましい.
選択的に水解されたS-9-PAHSA.

結論:

ステレオ化学はPAHSAの生物合成と分解に重要な役割を果たします.
脂肪組織における9 - PAHSAの内生的なステレオ化学は主にR−である.
エナンチオピュアPAHSAは,その活性と in vivoの代謝を理解するために不可欠です.

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