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).
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.
Song
Chuanjun
C
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, United Kingdom.
Tapaneeyakorn
Satita
S
Murphy
Annabel C
AC
Butts
Craig
C
Watts
Anthony
A
Willis
Christine L
CL
D001120:Arginine / Q000737:chemistry*; D002247:Carbon Isotopes / Q000737:chemistry; D006801:Humans; D007553:Isotope Labeling / Q000379:methods*; D008024:Ligands; D009496:Neurotensin / Q000737:chemistry*; D010446:Peptide Fragments / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*; D018028:Receptors, Neurotensin; D013237:Stereoisomerism
D002247:Carbon Isotopes; D008024:Ligands; D010446:Peptide Fragments; D018028:Receptors, Neurotensin; C409806:neurotensin (9-13); C114036:neurotensin type 1 receptor; D009496:Neurotensin; D001120:Arginine; D011392:Proline