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Synthesis of novel phospholipids that bind phenylalkanols and hydroquinone via phospholipase D-catalyzed transphosphatidylation

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Title: Synthesis of novel phospholipids that bind phenylalkanols and hydroquinone via phospholipase D-catalyzed transphosphatidylation
Authors: Yamamoto, Yukihiro Browse this author
Kurihara, Hideyuki Browse this author →KAKEN DB
Miyashita, Kazuo Browse this author →KAKEN DB
Hosokawa, Masashi Browse this author →KAKEN DB
Keywords: Transphosphatidylation
Tyrosol
Phospholipid
Phospholipase D
Phenylalkanols
Issue Date: 31-Jan-2011
Publisher: Elsevier B.V.
Journal Title: New Biotechnology
Volume: 28
Issue: 1
Start Page: 1
End Page: 6
Publisher DOI: 10.1016/j.nbt.2010.06.014
PMID: 20601268
Abstract: Phenylalkanols such as tyrosol and hydroxytyrosol (h-tyrosol), which possess antioxidant and anticancer properties, were phosphatidylated by phospholipase D (PLD)-catalyzed transphosphatidylation. After a 24-h reaction of phosphatidylcholine (PC) and tyrosol with PLD, a new product was detected by TLC and identified to phosphatidyl-tyrosol by high resolution MS and NMR analyses. The optimum reaction conditions were as follows; soyPC 50 μmol, tyrosol 500 μmol, ethyl acetate 1.6 ml, PLD 1.6 U, 0.2 M sodium acetate buffer (pH 5.6) 0.8 ml, 37℃ for 24 h. Under the optimum reaction conditions, the yields of phosphatidyl-tyrosol, hydroquinone (HQ), 2-(4-aminophenyl) ethanol (4APE), h-tyrosol, and 2-phenylethanol (PEA) were 87 ± 3.7, 13 ± 1.3, 90 ± 2.3, 64 ± 5.5 and 85 ± 1.0 mol%, respectively. Furthermore, from the results of transphosphatidylation of soyPC with several phenylethanols and phenylpropanols, we established the following details about the reaction specificity of transphosphatidylation by PLD from Streptomyces sp: (1) Para-amino and para-hydroxyl groups in the benzene ring of PEA derivatives do not affect the transphosphatidylation by PLD, whereas meta-hydroxyl group slightly inhibits the transphosphatidylation. (2) Meta and ortho-methyl groups in the benzene ring of PEA derivatives also slightly inhibit the transphosphatidylation. (3) Secondary and tertiary alcohols and hydroquinone are difficult to transphosphatidylate by PLD.
Type: article (author version)
URI: http://hdl.handle.net/2115/44830
Appears in Collections:水産科学院・水産科学研究院 (Graduate School of Fisheries Sciences / Faculty of Fisheries Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 細川 雅史

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