87713-13-1Relevant academic research and scientific papers
Synthesis and spectroscopic characterization of derivatives of proteinogenic amino acids, simultaneously labelled with 13C, 15N and 2H in the backbone
Elemes, Yiannis,Ragnarsson, Ulf
, p. 935 - 936 (2007/10/03)
As typical examples of derivatives of proteinogenic α-amino acids, simultaneously labelled with the stable isotopes 13C, 2H and 15N in the backbone, Boc-L-[1,2-13C2, 2-2H, 15N]amino acids are synthesized in enantiopure form and spectroscopically characterized.
Synthesis of Amino Acid Derivatives Substituted in the Backbone with Stable Isotopes for Application in Peptide Synthesis
Lankiewicz, Leszek,Nyasse, Barthelemy,Fransson, Bengt,Grehn, Leif,Ragnarsson, Ulf
, p. 2503 - 2510 (2007/10/02)
Starting from the corresponding precursors, 1 and 2, the two well known procedures for asymmetric synthesis of amino acids, those of Schoellkopf and Oppolzer, were compared for the preparation of -labelled (substituted) Boc-leucine enantiomers.Although both gave the final products in comparable overall yields, analysis of optical purity by two independent chromatographic methods revealed that two procedures differed considerably in this respect.The enatiomeric excess found was 97.2 - 97.4 and 99.7percent, respectively.As a consequence, the latter method was preferred for the synthesis of a number of additional backbone-labelled Boc-derivatives of the three proteinogenic amino acids alanine, phenylalanine and tyrosine, including such deuteriated in the amino acid side-chain.These derivatives exemplify precursors suitable for chemical synthesis of specifically backbone-labelled peptides and should allow greater exploitation of the properties of the 13C and, especially, the 15N nuclei in structural studies.
