Evidence of Strict Stereospecificity in the Structure of sn-1,2-Diacyl-3-Acetyl-Glycerols from Euonymus maximowiczianus Seeds Using Nuclear Magnetic Resonance Spectroscopy.

Autor: Sidorov RA; Laboratory of Lipid metabolism, K.A. Timiryazev Institute of Plant Physiology, Russian Academy of Sciences, Moscow, Russia, 127276., Shashkov AS; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, 119991., Solovyev PA; Institute of Fine Chemical Technologies, Moscow Technological University, Moscow, Russia, 119571., Gorshkova EN; Laboratory of Lipid metabolism, K.A. Timiryazev Institute of Plant Physiology, Russian Academy of Sciences, Moscow, Russia, 127276., Tsydendambaev VD; Laboratory of Lipid metabolism, K.A. Timiryazev Institute of Plant Physiology, Russian Academy of Sciences, Moscow, Russia, 127276.
Jazyk: angličtina
Zdroj: Lipids [Lipids] 2018 Apr; Vol. 53 (4), pp. 437-445. Date of Electronic Publication: 2018 May 02.
DOI: 10.1002/lipd.12025
Abstrakt: Asymmetric, optically active sn-1,2-diacyl-3-acetyl-glycerols (AcDAG) have been known to scientists for several decades. However, to date, the problem of their structure has not been definitely resolved, which has led to a vast diversity of terms used for their designation in the literature. Using two-dimensional nuclear magnetic resonance, we have investigated AcDAG from the mature seeds of Euonymus maximowiczianus, from which we have been able to both identify a correlation of the methyl group in acetic acid residue with protons at the carbon atom at sn-3 position in the glycerol residue of the AcDAG molecule and, for the first time, demonstrate that this correlation is observed exclusively with one carbon atom at the α-position, but not with two as would have been expected in case of a racemic mixture. Moreover, results of our analysis of AcDAG isolated from the seeds of E. maximowiczianus directly confirm that diacylglycerol-3-acetyl-transferase is responsible for their biosynthesis, which reveals a strict specificity not only to acetyl-CoA as one of the substrates but also to the sn-3-position of the glycerol residue in sn-1,2-diacylglycerol during their biosynthesis.
(© 2018 AOCS.)
Databáze: MEDLINE
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