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Chemoenzymatic Syntheses of the Optically Active Hydroperoxides of Phosphatidylglycerol and Phosphatidylethanolamine with Lipase, Lipoxygenase, and Phospholipase D
Author(s) -
Yoneda Kenji,
Sasakura Keiji,
Tahara Shoichi,
Iwasa Junkichi,
Baba Naomichi,
Kaneko Takao,
Matsuo Mitsuyoshi
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199213361
Subject(s) - lipase , lipoxygenase , phosphatidylethanolamine , phosphatidylglycerol , chemistry , phospholipase a2 , phospholipase a1 , mass spectrometry , phospholipase , biochemistry , enzyme , organic chemistry , chromatography , phospholipid , membrane , phosphatidylcholine
The enantioselective, lipase‐catalyzed stearoylation of 2‐ O ‐benzylglycerol is the first step in one of the two synthetic routes to phosphatidylethanolaminehydroperoxide 1 . Compound 1 and the phosphatidylglycerolhydroperoxide 2 , prepared in a similar fashion, were both purified by thin‐layer chromatography, and their structures determined by NMR spectroscopy and mass spectrometry. Lipidhydroperoxides are important for medical research, since their formation in vivo may trigger diseases such as cancer and arteriosclerosis.