title: Syntheses of deuterium labeled prenyldiphosphate and prenylcysteine analogues for in vivo mass spectrometric quantification.
abstract: A Wittig reaction employing Li(CD3)2CP(C6H5)3 was used to prepare d6-farnesol and d6-geranylgeraniol. Reductive amination of aniline-2,3,4,5,6-d5 was used to prepare the unnatural isoprenoid analogues d5-anilinogeraniol and d5-anilinofarnesol. All of these deuterated isoprenols were elaborated into their diphosphate and cysteine thioether derivatives suitable for use as stable-isotope labeled standards for quantitative mass spectrometric analysis.
authors.affiliation: Department of Molecular and Cellular Biochemistry, University of Kentucky, Lexington, KY, 40536, USA.
authors.forename: Thangaiah
authors.initials: T
authors.lastname: Subramanian
authors.forename: Karunai Leela
authors.initials: KL
authors.lastname: Subramanian
authors.forename: Manjula
authors.initials: M
authors.lastname: Sunkara
authors.forename: Fredrick O
authors.initials: FO
authors.lastname: Onono
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Morris
authors.forename: H Peter
authors.initials: HP
authors.lastname: Spielmann
mesh_terms: D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D003903:Deuterium / Q000138:chemical synthesis*; D007553:Isotope Labeling; D013058:Mass Spectrometry / Q000379:methods; D011106:Polyisoprenyl Phosphates / Q000138:chemical synthesis*
chemical_list: D011106:Polyisoprenyl Phosphates; C542732:prenylcysteine; D003903:Deuterium; D003545:Cysteine; C002963:geranylgeranyl pyrophosphate
keywords: AFPP; AGPP; FPP; FTase; GGPP; mass standards; protein prenylation; stable labeled synthesis