title: Large-scale preparation of (13) C-labeled 2-(phenylthio)acetic acid and the corresponding labeled sulfoxides and sulfones.
abstract: We have developed large-scale efficient procedures for the conversion of commercially available [(13) C]- or [(2) H3 ,(13) C]methanol and (13) CO2 or (13) C-labeled bromoacetic acid to 2-(phenylthio)[1,2-(13) C2 ]-, [1-(13) C]-, and [2-(13) C]acetic acid. The resulting derivatives are versatile, chemically stable, and nonvolatile two-carbon labeling precursors. We have used the (13) C-isotopomers of 2-(phenylthio)acetic acid in the synthesis of (13) C-labeled acrylic acid, methacrylic acid, and trans-crotonic acid.
authors.affiliation: The National Stable Isotope Resource, Los Alamos National Laboratory, Los Alamos, NM, USA; Bioenergy and Environmental Science Group, Bioscience Division, Los Alamos National Laboratory, Los Alamos, NM, USA; Department of Chemistry, New Mexico Highlands University, Box 9000, Las Vegas, NM 87701, USA.
authors.forename: Rodolfo A
authors.initials: RA
authors.lastname: Martinez
authors.forename: David R
authors.initials: DR
authors.lastname: Glass
authors.forename: Erick G
authors.initials: EG
authors.lastname: Ortiz
authors.forename: Marc A
authors.initials: MA
authors.lastname: Alvarez
authors.forename: Ernesto
authors.initials: E
authors.lastname: Juarez
authors.forename: Siegfried N
authors.initials: SN
authors.lastname: Lodwig
authors.forename: Clifford J
authors.initials: CJ
authors.lastname: Unkefer
mesh_terms: D002247:Carbon Isotopes / Q000138:chemical synthesis; D006016:Glycolates / Q000138:chemical synthesis*; D007553:Isotope Labeling / Q000379:methods; D013450:Sulfones / Q000138:chemical synthesis*; D013454:Sulfoxides / Q000138:chemical synthesis*
chemical_list: D002247:Carbon Isotopes; D006016:Glycolates; D013450:Sulfones; D013454:Sulfoxides; C005446:thiophenoxyacetic acid
keywords: 13C-labeled synthons; 2-(phenylthio)[1,2-13C2]acetic acid; stable isotope labeling