Enantioselective syntheses of alpha-Fmoc-Pbf-[2-(13)C]-L-arginine and Fmoc-[1,3-(13)C2]-L-proline and Incorporation into the neurotensin receptor 1 ligand, NT(8-13).

Journal article

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.

Authors: Song, C; Tapaneeyakorn, S; Murphy, A; Butts, C; Watts, A

• Publication status: Published
• Journal: Journal of organic chemistry
• Volume: 74
• Issue: 23
• Pages: 8980-8987
• Publication date: 2009-12-01
• DOI: 10.1021/jo9014497
• EISSN: 1520-6904
• ISSN: 0022-3263
• Language: English
• Keywords: Neurotensin; Ligands; Peptide Fragments; Receptors, Neurotensin; Carbon Isotopes; Stereoisomerism; Arginine; Humans; Isotope Labeling; Proline