Large-scale preparation of (13) C-labeled 2-(phenylthio)acetic acid and the corresponding labeled sulfoxides and sulfones

Rodolfo A Martinez; David R Glass; Erick G Ortiz; Marc A Alvarez; Ernesto Juarez; Siegfried N Lodwig; Clifford J Unkefer

doi:10.1002/jlcr.2991

Large-scale preparation of (13) C-labeled 2-(phenylthio)acetic acid and the corresponding labeled sulfoxides and sulfones

J Labelled Comp Radiopharm. 2013 Feb;56(2):31-5. doi: 10.1002/jlcr.2991. Epub 2013 Jan 16.

Authors

Rodolfo A Martinez¹, David R Glass, Erick G Ortiz, Marc A Alvarez, Ernesto Juarez, Siegfried N Lodwig, Clifford J Unkefer

Affiliation

¹ 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.

PMID: 24285279
DOI: 10.1002/jlcr.2991

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.

Keywords: 13C-labeled synthons; 2-(phenylthio)[1,2-13C2]acetic acid; stable isotope labeling.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Carbon Isotopes / chemical synthesis
Glycolates / chemical synthesis*
Isotope Labeling / methods
Sulfones / chemical synthesis*
Sulfoxides / chemical synthesis*

Substances

Carbon Isotopes
Glycolates
Sulfones
Sulfoxides
thiophenoxyacetic acid

Grants and funding

P41RR02231/RR/NCRR NIH HHS/United States