Asymmetric synthesis of L-[4-13C]lysine by alkylation of oxazinone derivative as a chiral glycine equivalent

• Published in: Journal of labelled compounds & radiopharmaceuticals Vol. 47; no. 11; pp. 787 - 795
• Main Authors: Takatori, Kazuhiko, Hayashi, Akira, Kajiwara, Masahiro
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 15.10.2004; Wiley
• Subjects: Aliphatic compounds; Biochemical Research Methods; Biochemistry & Molecular Biology; Chemistry; Chemistry, Analytical; Chemistry, Medicinal; chiral glycine equivalent; Exact sciences and technology; L-[4-13C]lysine; labeled amino acid; Life Sciences & Biomedicine; Organic chemistry; oxazinone; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; Science & Technology; chiral glycine equivalent; C-13; labeled amino acid; ENANTIOSELECTIVE SYNTHESIS; DELTA-AMINOLEVULINIC-ACID; LYSINE; ALPHA-AMINO-ACIDS; L-[4-C-13] lysine; oxazinone; α-Aminoacid; Isotope labelling; Asymmetric synthesis; Lysine; Sodium Acetate; Carbon Isotopes; Glycine; Oxazine derivatives; Chemical synthesis; Carbon 13; Labelled compound
• ISSN: 0362-4803; 1099-1344
• DOI: 10.1002/jlcr.868

L‐[4‐13C]Lysine (2) was synthesized from sodium [2‐13C]acetate (3) and Dellaria's oxazinone 1 as a chiral glycine equivalent. Wittig reaction of the glycinal 7 and 13C‐labeled phosphonium ylide 5, prepared from sodium [2‐13C]acetate (3), gave the α, β‐unsaturated ester 8. The ester 8 was converted to the allylic bromide 10. Alkylation of the oxazinone 1 with 10 proceeded with high diastereoselectivity. Ethanolysis, hydrogenation of the double bond with diimide, removal of the chiral auxiliary, and hydrolysis gave L‐[4‐13C]lysine (2). Copyright © 2004 John Wiley & Sons, Ltd.