129243-79-4Relevant academic research and scientific papers
Enantioselective synthesis of isotopically labelled α-amino acids. Preparation of (ε-13C)-L-α-aminoadipic acid and five isotopomers of L-lysine with 13C, 15N and 2H in the δ and ε-positions
Raap, J.,Wielen, C. M. van der,Lugtenburg, J.
, p. 277 - 286 (2007/10/02)
An asymmetric synthesis of the six-carbon α-amino acids (ε-13C)-L-α-aminoadipic acid and various isotopomers of L-lysine is described.The synthesis is based on a general method starting from the bis-lactim ether of cyclo(D-Val-Gly) and simple labelled reagents like K(13)CN, K(13)C15N, (13)CH3CN and LiAl(2)H4.Using this route (ε-13C)-L-α-aminoadipic acid was prepared in 31percent yield based on the labelled potassium cyanide.Five different isotopomers of L-lysine were prepared in high overall yield (45percent based on the labelled starting compound): (ε-13C)-L-lysine,(ε-13C,ε-15N)-L-lysine, (δ-13C)-L-lysine, (ε-2H2)-L-lysine and (ε-13C,ε-2H2)-L-lysine.The isotopomers were characterized using various spectroscopic techniques, e.g., 1H NMR, 2H NMR, 13C NMR, 15N NMR and mass spectrometry.The 31.2-ppm and the 27.6-ppm peak in the 13C NMR spectrum of lysine could be unambiguously assigned to the β- and δ-carbons, respectively.This means that the assignment previously reported is incorrect.
