title: Enantiopure synthesis of side chain-modified α-amino acids and 5-cis-alkylprolines.
abstract: A short, concise synthesis of enantiopure, side chain-modified α-amino acids such as 4-oxo-L-norvaline, 6-oxo-L-homonorleucine, and 5-cis-alkyl prolines is described. Knoevenagel condensation of l-aminocarboxylate-derived β-ketoesters with aldehydes followed by reductive decarboxylation results in unnatural α-amino acids in good yield. A fluorescent amino acid is synthesized using a similar protocol. These studies show that aminocarboxylate-derived β-ketoesters are very useful intermediates and the method employed is both general and practical for the preparation of γ(δ)-oxo α-amino acids and alkylprolines.
authors.affiliation: Department of Chemistry, Mendeleev Block, Indian Institute of Science Education and Research, Pune, Maharashtra, 411008, India.
authors.forename: Amar R
authors.initials: AR
authors.lastname: Mohite
authors.forename: Ramakrishna G
authors.initials: RG
authors.lastname: Bhat
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000622:Aminolevulinic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007930:Leucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009646:Norleucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C575978:4-oxo-L-norvaline; C575979:6-oxo-L-homonorleucine; D000596:Amino Acids; D009646:Norleucine; D000622:Aminolevulinic Acid; D011392:Proline; D007930:Leucine