Gas chromatography-mass spectrometry of monohydroxyeicosatetraenoic acids as their methyl esters trimethylsilyl, allyldimethylsilyl and tert.-butyldimethylsilyl ethers

Steffenrud, S.; Borgeat, Pierre; Salari, Hassan; Evans, Michael J.; Bertrand, Michel

doi:10.1016/0378-4347(87)80506-6

Cited by 19 publications

(7 citation statements)

References 23 publications

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“…McLafferty rearrangement from the methyl ester/ADMS derivative of 5‐hydroxyeicosa‐6,8,11,14‐tetraenoic acid ( 272 ) (Steffenrud et al., ).…”

Section: Other Silyl Derivativesmentioning

confidence: 99%

“…87) derivatives of hydroxy long-chain fatty acid methyl esters, exemplified by 5-,12-, and 15-monohydroxyeicosanoic acids, have been shown to produce intense [M − 57] + and [M − 41] + ions respectively followed by elimination of methanol (42 u, presumably from the SCHEME 197. McLafferty rearrangement from the methyl ester/ADMS derivative of 5-hydroxyeicosa-6,8,11,14-tetraenoic acid (272) (Steffenrud et al, 1987b). SCHEME 198. formation of the ion at m/z 435 (pn) from the ADMS derivative of leukotriene LTB 4 (273) (Steffenrud et al, 1986).…”

Section: Ivf2 Allyldimethylsilyl (Adms) Derivativesmentioning

confidence: 99%

“…Derivatized prostaglandins yield abundant [M − 41] + ions but leukotriene LTB 4 (273) does not. Instead, the major fragmentation is α-cleavage of the C12-C13 bond to give the stabilized tetraunsaturated ion pn (Scheme 198) (Steffenrud et al, 1986(Steffenrud et al, , 1987b.…”

Section: Ivf2 Allyldimethylsilyl (Adms) Derivativesmentioning

confidence: 99%

“…b) considerably reduced the relative abundance of both the [M − 57] + and [M − 41] + ions and also complicated the spectra. Chain cleavages were more important than loss of tert ‐butyl or allyl groups with reactions involving proposed McLafferty rearrangements from the cleavage products prominent in the spectra of the methyl ester/ADMS derivative of 5‐hydroxyeicosa‐6,8,11,14‐tetraenoic acid ( 269 , m/z 155, Scheme ) (Steffenrud et al, ).…”

Section: Other Silyl Derivativesmentioning

confidence: 99%

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Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Harvey

Vouros

2019

Mass Spectrometry Reviews

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This review describes the mass spectral fragmentation of trimethylsilyl (TMS) and related alkylsilyl derivatives used for preparing samples for analysis, mainly by combined gas chromatography and mass spectrometry (GC/MS). The review is divided into three sections. The first section is concerned with the TMS derivatives themselves and describes fragmentation of derivatized alcohols, thiols, amines, ketones, carboxylic acids and bifunctional compounds such as hydroxy‐ and amino‐acids, halo acids and hydroxy ethers. More complex compounds such as glycerides, sphingolipids, carbohydrates, organic phosphates, phosphonates, steroids, vitamin D, cannabinoids, and prostaglandins are discussed next. The second section describes intermolecular reactions of siliconium ions such as the TMS cation and the third section discusses other alkylsilyl derivatives. Among these latter compounds are di‐ and trialkyl‐silyl derivatives, various substituted‐alkyldimethylsilyl derivatives such as the tert‐butyldimethylsilyl ethers, cyclic silyl derivatives, alkoxysilyl derivatives, and 3‐pyridylmethyldimethylsilyl esters used for double bond location in fatty acid spectra. © 2019 Wiley Periodicals, Inc. Mass Spec Rev 0000:1–107, 2019

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“…McLafferty rearrangement from the methyl ester/ADMS derivative of 5‐hydroxyeicosa‐6,8,11,14‐tetraenoic acid ( 272 ) (Steffenrud et al., ).…”

Section: Other Silyl Derivativesmentioning

confidence: 99%

Section: Ivf2 Allyldimethylsilyl (Adms) Derivativesmentioning

confidence: 99%

Section: Ivf2 Allyldimethylsilyl (Adms) Derivativesmentioning

confidence: 99%

Section: Other Silyl Derivativesmentioning

confidence: 99%

See 2 more Smart Citations

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Harvey

Vouros

2019

Mass Spectrometry Reviews

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“…The most important are the alkyldimethylsilyl reagents containing a propyl, isopropyl or tert.-butyl substituent [456][457][458][459]. The tert.butyldimethylsilyl chloride, N-methyl-N-(tert.-butyldimethylsilyl) trifluoroacetamide, and tert.-butyldimethylsilylimidazole reagents are now commercially available which has done much to popularize their general use for derivatizing amino acids [460][461][462][463], organic acids [464,465], alcohols [457,466] and thiols [467]. The increase in hydrolytic stability results from the bulkiness of the alkyldimethylsilyl group, which in turn also influences the rate and extent of derivative formation under conditions influenced by stereochemical considerations.…”

Section: Derivatization Techniques For Gas Chromatographymentioning

confidence: 99%