Pentafluorobenzyl prostaglandins

Pentafluorobenzyl bromide has been used in the derivatization of mercaptans [55] and phenols [36], m the analysis of prostaglandins [37], and in quantitative GC-MS [5S] 1,3 Dichlorotetrafluoroacetone is used for the derivatization of amino acids to the corresponding cyclic oxazolidinones and allows the rapid analysis of all 20 protein ammo acids [d] Pentafluorophenyldialkylchlorosilane derivatives have facilitated the gas chromatographic analysis of a wide range of functionally substituted organic compounds, including steroids, alcohols, phenols, amines, carboxylic acids, and chlorohydrms [4]... 

Lee et al. [41] developed a method for the quantitative analysis of enantiomers and regioisomers of fatty acids, hydroxy fatty acids, and related substances, including several HETEs and prostaglandins. The method is based on pre-column derivatization to pentafluorobenzyl derivatives and subsequent LC-MS analysis in an organic mobile phase using electron-capture negative-ionization (ECNI). The method is applied to lipidomic profiling, for instance of rat epithehal cells. 

If the analytical method is aimed only at detecting carbonyl containing compounds, various oximes may be prepared instead methyl esters of pentafluorobenzyl oximes or p-nitrobenzyl oximes of prostaglandins of the E, D, 6-keto-E or 6-keto-F type as well as of TXB2 have been analyzed by GC/MS methods or HPLC methods, respectively [357,367-369]. 

Methyl ester-HFB derivatives have been employed in prostaglandin analysis by GC-MS [140], but most applications employ methyl ester—silyl derivatives (see Section 3) or mixed pentafluorobenzyl ester derivatives for NICI (Section 5, below). 

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