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Enantioselective syntheses of selectively labeled, orthogonally protected [2-(13)C]-L-arginine and [1,3-(13)C(2)]-L-proline are described from the commercially available precursors [2-(13)C]bromoacetic acid and potassium [(13)C]cyanide. Interestingly the enhanced signal assigned to C-2 in the (13)C NMR spectrum of alpha-Fmoc-Pbf-[2-(13)C]-L-arginine was very broad at room temperature. The two Fmoc-labeled amino acids were used to prepare [2-(13)C]-Arg9 and [1,3-(13)C(2)]-Pro10 labeled ligand (NT(8-13)) by manual Fmoc-SPSS.

Original publication

DOI

10.1021/jo9014497

Type

Journal article

Journal

J Org Chem

Publication Date

04/12/2009

Volume

74

Pages

8980 - 8987

Keywords

Arginine, Carbon Isotopes, Humans, Isotope Labeling, Ligands, Neurotensin, Peptide Fragments, Proline, Receptors, Neurotensin, Stereoisomerism