Evidence of Strict Stereospecificity in the Structure ofsn-1,2-Diacyl-3-Acetyl-Glycerols fromEuonymus maximowiczianusSeeds Using Nuclear Magnetic Resonance Spectroscopy
| Autor: | Pavel A. Solovyev, R. A. Sidorov, Vladimir D. Tsydendambaev, Elena N. Gorshkova, Alexander S. Shashkov |
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| Rok vydání: | 2018 |
| Předmět: |
Glycerol
0301 basic medicine Magnetic Resonance Spectroscopy Molecular Structure 030102 biochemistry & molecular biology Stereochemistry Euonymus Organic Chemistry Stereoisomerism Cell Biology Nuclear magnetic resonance spectroscopy Biochemistry 03 medical and health sciences Acetic acid chemistry.chemical_compound Residue (chemistry) 030104 developmental biology Stereospecificity chemistry Seeds Racemic mixture Molecule Two-dimensional nuclear magnetic resonance spectroscopy Methyl group |
| Zdroj: | Lipids. 53:437-445 |
| ISSN: | 0024-4201 |
| DOI: | 10.1002/lipd.12025 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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