An efficient and convenient synthesis of deuterium-labelled seminolipid isotopomers and their ESI-MS characterization

Franchini, L.; Panza, Luigi; Kongmanas, Kessiri; Tanphaichitr, Nongnuj; Faull, Kym F.; Ronchetti, Fiamma

doi:10.1016/j.chemphyslip.2008.02.002

Cited by 10 publications

(12 citation statements)

References 23 publications

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“…As expected, the internal standard and unlabeled SGG were virtually indistinguishable on the basis of reverse-phase retention time ( Fig. 4 ) and collisionally activated dissociation conditions ( 24 ). With this internal standard, it was possible to accurately quantitate SGG in crude total lipid extracts from tissues and cells without further purifi cation of the samples.…”

Section: Discussionmentioning

confidence: 74%

“…Following HPTLC with Coomassie Blue staining, the product showed a single band with an R f of 0.659. During positive ion ESI in the presence of lithium, the fi nal product gave an intense ion at m/z 723.3 ( 24 ) corresponding to the lithiated adduct (calculated as 723.5953 for C 41 H 80 O 9 Li). This sample was quantifi ed by weighing and used as the HPTLC reference standard.…”

Section: Preparation Of Sgg and Ggmentioning

confidence: 99%

“…Because we were unable to purify a molecularly homogeneous preparation of SGG from natural sources, it was necessary to chemically synthesize C16:0/C16:0 SGG as a quantitative standard. To use it as an internal standard, it was prepared as 2 H 3 -C16:0/ C16:0 SGG by incorporating stable deuterium atoms into the molecule as part of the synthesis scheme ( 24 ). The MRM-determined concentration of C16:0/C16:0 SGG in mouse testes was about 550 µg/g testis ( Table 1 and Fig.…”

Section: Compensatory Expression Of the Cgt Polypeptidementioning

confidence: 99%

“…( Fig. 1B ) was chemically synthesized as previously described ( 24 ). The fi nal product was molecularly homogeneous by NMR and mass spectral criteria.…”

Section: Sgg Quantifi Cationmentioning

confidence: 99%

“…with specifi c measurement of the major C16:0/C16:0 isoform using 2 H 3 -C16:0-alkyl/C16:0-acyl SGG, synthesized as previously described ( 24 ) as the internal standard. Further, the MRM method was used to quantify C16:0/C16:0 SGG in testes and sperm of fertile Cgt heterozygous male mice.…”

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confidence: 99%

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Quantification of seminolipid by LC-ESI-MS/MS-multiple reaction monitoring: compensatory levels in Cgt mice

Kongmanas

Yaghoubian

et al. 2010

Journal of Lipid Research

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This article is available online at http://www.jlr.org Seminolipid, 1-O -alkyl-2-O -acyl[ ␤ -D-(3 ′ -sulfatoxy)galactopyranosyl(1'-3)] sn -glycerol, also known as sulfogalactosylglycerolipid (SGG) and SM4g ( Fig. 1A ), is present selectively and substantially in mammalian male germ cells, comprising about 10 mol% of total lipids ( 1 ). SGG consists of glycerol with a sn -1 alkyl and sn -2 acyl chain as the lipid backbone, and a (3 ′ -sulfo)-galactopyranose ␤ -linked to the sn -3 position. Consistently across mammalian species studied so far, C16:0/C16:0 SGG is the main molecular species ( 1, 2 ), although minor molecular species, such as C16:0/C14:0, C14:0/C16:0, C15:0/C16:0, C17:0/C16:0, C16:0/C18:0, C18:0/C16:0, and C17:0/C18:0 SGG, representing < 10% of the main species, have also been described ( 3, 4 ). Accumulated evidence has pointed to the signifi cance of SGG for mammalian male reproduction ( 1 ). SGG on the sperm surface is involved in sperm-zona pellucida (ZP) binding and sperm-egg plasma membrane binding ( 5, 6 ). As a structurally ordered lipid, SGG participates in the formation of lipid rafts in the sperm head, which act as platforms for ZP binding ( 7-10 ). Genetic deletion of Cgt and Cst , coding for two enzymes (ceramide galactosyltransferase and cerebroside sulfotransferase, respectively) in the SGG biosynthetic pathway, leads to spermatogenesis arrest in the primary spermatocyte stage and, thus, male infertility ( 11, 12 ).Due to its physiological signifi cance, an accurate, sensitive, specifi c method for SGG quantifi cation is needed. A simple colorimetric Azure A assay has been conventionally

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Section: Discussionmentioning

confidence: 74%

Section: Preparation Of Sgg and Ggmentioning

confidence: 99%

Section: Compensatory Expression Of the Cgt Polypeptidementioning

confidence: 99%

“…( Fig. 1B ) was chemically synthesized as previously described ( 24 ). The fi nal product was molecularly homogeneous by NMR and mass spectral criteria.…”

Section: Sgg Quantifi Cationmentioning

confidence: 99%

mentioning

confidence: 99%

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Quantification of seminolipid by LC-ESI-MS/MS-multiple reaction monitoring: compensatory levels in Cgt mice

Kongmanas

Yaghoubian

et al. 2010

Journal of Lipid Research

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Syntheses of deuterium‐labelled cholesteryl neoglycolipids

Lafont

Boullanger

Gambetta

2012

Labelled Comp Radiopharmac

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Synthesis of ¹³C‐labelled cutin and suberin monomeric dicarboxylic acids of the general formula HO₂¹³C‐(CH₂)_n‐¹³CO₂H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28)

Schink

Spielvogel

Imhof

2020

Labelled Comp Radiopharmac

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13C‐labeled dicarboxylic acids HO213C‐(CH2)n‐13CO2H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28) have been synthesized as internal standards for LC‐MS and GC‐MS analysis of cutin and suberin monomer degradation by soil‐based microorganisms. Different synthetic strategies had to be applied depending on the chain length of the respective synthetic target and because of economic considerations. 13C‐labels were introduced by nucleophilic substitution of a suitable leaving group with labelled potassium cyanide and subsequent hydrolysis of the nitriles to produce the corresponding dicarboxylic acids. All new compounds are characterized by GC/MS, IR, and NMR methods as well as by elemental analysis.

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An efficient and convenient synthesis of deuterium-labelled seminolipid isotopomers and their ESI-MS characterization

Cited by 10 publications

References 23 publications

Quantification of seminolipid by LC-ESI-MS/MS-multiple reaction monitoring: compensatory levels in Cgt mice

Quantification of seminolipid by LC-ESI-MS/MS-multiple reaction monitoring: compensatory levels in Cgt mice

Syntheses of deuterium‐labelled cholesteryl neoglycolipids

Synthesis of ¹³C‐labelled cutin and suberin monomeric dicarboxylic acids of the general formula HO₂¹³C‐(CH₂)_n‐¹³CO₂H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28)

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An efficient and convenient synthesis of deuterium-labelled seminolipid isotopomers and their ESI-MS characterization

Cited by 10 publications

References 23 publications

Quantification of seminolipid by LC-ESI-MS/MS-multiple reaction monitoring: compensatory levels in Cgt mice

Quantification of seminolipid by LC-ESI-MS/MS-multiple reaction monitoring: compensatory levels in Cgt mice

Syntheses of deuterium‐labelled cholesteryl neoglycolipids

Synthesis of 13C‐labelled cutin and suberin monomeric dicarboxylic acids of the general formula HO213C‐(CH2)n‐13CO2H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28)

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Synthesis of ¹³C‐labelled cutin and suberin monomeric dicarboxylic acids of the general formula HO₂¹³C‐(CH₂)_n‐¹³CO₂H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28)