Medizinische Universität Graz Austria/Österreich - Forschungsportal - Medical University of Graz
Gewählte Publikation:
Stadler, P; Zandonella, G; Haalck, L; Spener, F; Hermetter, A; Paltauf, F.
Inhibition of microbial lipases with stereoisomeric triradylglycerol analog phosphonates.
Biochim Biophys Acta. 1996; 1304(3):229-244
Doi: 10.1016/S0005-2760(96)00123-3
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- Co-Autor*innen der Med Uni Graz
- Spener Friedrich
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- Abstract:
- 1,2(2,3)-Diradylglycero O-(p-nitrophenyl) n-hexylphosphonates were synthesized, with the diradylglycerol moiety being di-O-octylglycerol, 1-O-hexadecyl-2-O-pyrenedecanylglycerol, or 1-O-octyl-2-oleoyl-glycerol, and tested for their ability to inactivate lipases from Chromobacterium viscosum (CVL) and Rhizopus oryzae (ROL). The experimental data indicate the formation of stable, covalent 1:1 enzyme-inhibitor adducts with the di-O-alkylglycero phosphonates. The differences in reactivity of diastereomeric phosphonates with opposite configuration at the glycerol backbone was less expressed with both enzymes tested as compared to the influence of the stereochemistry at the phosphorus. Both lipases exhibited the same preference for the chirality at the phosphorus that was independent from the absolute configuration at the glycerol backbone. However, with CVL and ROL the inhibitors with the active site serine-directed phosphonate linked at position sn-1 of the glycerol moiety reacted significantly faster than the corresponding sn-3 analogs, reflecting the sn-1 stereopreference of the enzymes towards triacylglycerol analogs with a sn-2 O-alkyl substituent. In contrast, the phosphonates based on the 1-O-octyl-2-oleoylglycerol did not significantly inactivate CVL. Unexpectedly, these substances were hydrolyzed in the presence of lipase.
- Find related publications in this database (using NLM MeSH Indexing)
- Chromatography, High Pressure Liquid -
- Chromobacterium - enzymology
- Diglycerides - chemical synthesis Diglycerides - pharmacology
- Enzyme Inhibitors - pharmacology
- Glycerol - analogs and derivatives
- Kinetics -
- Lipase - antagonists and inhibitors
- Molecular Conformation -
- Nitrophenols - metabolism
- Phosphonic Acids - chemical synthesis Phosphonic Acids - pharmacology
- Rhizopus - enzymology
- Stereoisomerism -
- Find related publications in this database (Keywords)
- microbial lipase
- inhibition
- phosphonate
- triacylglycerol analog
- fluorescent pyrene lipid
- stereoselectivity