204451-46-7Relevant academic research and scientific papers
Synthesis of (ε-13C-,ε-15N)-enriched L-lysine - Establishing schemes for the preparation of all possible 13C and 15N isotopomers of L-lysine, L-ornithine, and L-proline
Siebum, Arjan H. G.,Tsang, Robert K. F.,Van Der Steen, Rob,Raap, Jan,Lugtenburg, Johan
, p. 4391 - 4396 (2007/10/03)
In this paper we describe a simple synthetic strategy that, with the right rational adaptation, gives direct access to any 13C/15N isotopomer of L-glutamate, L-ornithine, L-proline, L-lysine, and L-α, amino adipic acid. This strategy also allows access to nonproteinogenic amino acids like L-citrulline in high yields and optical purity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
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.
