81202-06-4Relevant articles and documents
Stereoselective synthesis of stable isotope-labeled L-α-amino acids: Enantioselective synthesis of 13C-, 15N-labeled L-proline using Oppolzer's glycine template
Lodwig, Siegfried N.,Unkefer, Clifford J.
, p. 983 - 991 (1998)
We have developed a stereoselective route to the synthesis of stable isotope-labeled L-proline. Alkylation of (2R)-N-{N'-[bis(methylthio)methylidine]glycyl}bornane-10,2-sultam with 3-chloro-iodopropane yielded (2R)-N-{(2'S)-2'-{[Bis(methylthio)methylidine]amino}5-chloropentan-1 -oyl}bornane-10,2-sultam. Cyclization to the imino acid occurred during the sequential removal of the α-amino protecting group and the chiral auxiliary.
Enantioselective syntheses of α-Fmoc-Pbf-[2-13C]-L- arginine and Fmoc-[1,3-13C2]-L-proline and incorporation into the neurotensin receptor 1 ligand, NT8-13
Song, Chuanjun,Tapaneeyakorn, Satita,Murphy, Annabel C.,Butts, Craig,Watts, Anthony,Willis, Christine L.
experimental part, p. 8980 - 8987 (2010/03/02)
(Chemical Equation Presented) Enantioselective syntheses of selectively labeled, orthogonally protected [2-13C]-L-arginine and [1,3- 13C2]-L-proline are described from the commercially available precursors [2-13C]bromoacetic acid and potassium [ 13C]cyanide. Interestingly the enhanced signal assigned to C-2 in the 13C NMR spectrum of α-Fmoc-Pbf-[2-13C]-L-arginine was very broad at room temperature. The two Fmoc-labeled amino acids were used to prepare [2-13C]-Arg9 and [1,3-13C2]-Pro10 labeled ligand (NT8-13) by manual Fmoc-SPSS.