scholarly journals Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450

2009 ◽  
Vol 51 (5) ◽  
pp. 1125-1133 ◽  
Author(s):  
Danièle Lucas ◽  
Sophie Goulitquer ◽  
Jan Marienhagen ◽  
Maude Fer ◽  
Yvonne Dreano ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Double Bond ◽  
Polyunsaturated Fatty Acids ◽  
Cytochromes P450 ◽  
Stereoselective Epoxidation

scholarly journals Regioselective and Stereoselective Epoxidation of n-3 and n-6 Fatty Acids by Fungal Peroxygenases

Antioxidants ◽  
2021 ◽  
Vol 10 (12) ◽  
pp. 1888
Author(s):  
Alejandro González-Benjumea ◽  
Dolores Linde ◽  
Juan Carro ◽  
René Ullrich ◽  
Martin Hofrichter ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Double Bond ◽  
Chemical Synthesis ◽  
Polyunsaturated Fatty Acids ◽  
Chiral Hplc ◽  
Pharmacological Activities ◽  
Racemic Mixtures ◽  
Synthetic Utility ◽  
Stereoselective Epoxidation

Epoxide metabolites from n-3 and n-6 polyunsaturated fatty acids arouse interest thanks to their physiological and pharmacological activities. Their chemical synthesis has significant drawbacks, and enzymes emerge as an alternative with potentially higher selectivity and greener nature. Conversion of eleven eicosanoid, docosanoid, and other n-3/n-6 fatty acids into mono-epoxides by fungal unspecific peroxygenases (UPOs) is investigated, with emphasis on the Agrocybe aegerita (AaeUPO) and Collariella virescens (rCviUPO) enzymes. GC-MS revealed the strict regioselectivity of the n-3 and n-6 reactions with AaeUPO and rCviUPO, respectively, yielding 91%-quantitative conversion into mono-epoxides at the last double bond. Then, six of these mono-epoxides were obtained at mg-scale, purified and further structurally characterized by 1H, 13C and HMBC NMR. Moreover, chiral HPLC showed that the n-3 epoxides were also formed (by AaeUPO) with total S/R enantioselectivity (ee > 99%) while the n-6 epoxides (from rCviUPO reactions) were formed in nearly racemic mixtures. The high regio- and enantioselectivity of several of these reactions unveils the synthetic utility of fungal peroxygenases in fatty acid epoxidation.

Structural Homogeneity in Unsaturated Fatty Acids of Marine Lipids. A Review

1964 ◽  
Vol 21 (2) ◽  
pp. 247-254 ◽  
Author(s):  
R. G. Ackman
Keyword(s):  
Fatty Acids ◽  
Double Bond ◽  
Polyunsaturated Fatty Acids ◽  
Chain Length ◽  
Unsaturated Fatty Acids ◽  
Analytical Data ◽  
Double Bonds ◽  
Marine Origin ◽  
Methyl Group ◽  
Marine Lipids

Consideration of recent analytical data supports the conclusion that the longer-chain polyunsaturated fatty acids of marine origin are all structurally homogeneous in that the double bonds are cis, the double bonds methylene interrupted, and that, with the exception of the C16 chain length, the ultimate double bond will normally be three, six or nine carbon atoms removed from the terminal methyl group.

Double-bond location in long-chain polyunsaturated fatty acids by chemical lonization-mass spectrometry

Lipids ◽  
1983 ◽  
Vol 18 (12) ◽  
pp. 853-858 ◽  
Author(s):  
Jan Lankelma ◽  
Eser Ayanoglu ◽  
Carl Djerassi
Keyword(s):  
Mass Spectrometry ◽  
Fatty Acids ◽  
Double Bond ◽  
Polyunsaturated Fatty Acids ◽  
Long Chain

scholarly journals Determination of double bond positions in polyunsaturated fatty acids by mass spectrometry.

1983 ◽  
Vol 31 (9) ◽  
pp. 3228-3232 ◽  
Author(s):  
AKIHIKO KAWAGUCHI ◽  
YOKO KOBAYASHI ◽  
YUJI OGAWA ◽  
SHIGENOBU OKUDA
Keyword(s):  
Mass Spectrometry ◽  
Fatty Acids ◽  
Double Bond ◽  
Polyunsaturated Fatty Acids
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