Phospholipase D-catalyzed transphosphatidylation in anhydrous organic solvents.
A new reaction system suitable for phospholipase D (PLD)-catalyzed transphosphatidylation of alcohols with phosphatidylcholine under anhydrous conditions is reported. The key innovation of the reaction system is a cation-exchange resin serving as a scavenger for choline that forms as a byproduct in the transphosphatidylation reaction. Due to the absence of water in this system, the reaction path dramatically shifts in favor of the target transphosphatidylated product, whereas the undesirable side hydrolysis of phosphatidylcholine is completely suppressed, in contrast to commonly used biphasic water-organic systems. In addition, a salt activation technique is successfully applied to increase the catalytic activity of PLD in this anhydrous system. The new reaction system is successfully used for transphosphatidylation of a wide range of primary, secondary, and aromatic alcohols catalyzed by PLD from Streptomyces sp.
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EnzyMed Division, Albany Molecular Research, Inc., 2501 Crosspark Road, Iowa City, Iowa 52242, USA.
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D015060:1,2-Dipalmitoylphosphatidylcholine / Q000378:metabolism*; D000438:Alcohols / Q000378:metabolism*; D000837:Anion Exchange Resins; D002725:Chloroform / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D015394:Molecular Structure; D010739:Phospholipase D / Q000378:metabolism*; D012117:Resins, Synthetic; D012997:Solvents / Q000737:chemistry; D013302:Streptomyces / Q000201:enzymology*
D000438:Alcohols; D000837:Anion Exchange Resins; D012117:Resins, Synthetic; D012997:Solvents; D015060:1,2-Dipalmitoylphosphatidylcholine; D002725:Chloroform; C024946:Amberlite IRC50; D010739:Phospholipase D