title: Asymmetric synthesis of sterically and electronically demanding linear ω-trifluoromethyl containing amino acids via alkylation of chiral equivalents of nucleophilic glycine and alanine.
abstract: An operationally convenient, scalable asymmetric synthesis of linear, ω-trifluoromethyl-containing amino acids, which were not previously produced in their enantiomerically pure form, has been developed via alkylation of chiral equivalents of nucleophilic glycine and alanine. The simplicity of the experimental procedures and high stereochemical outcome (yields up to 90% and diastereoselectivity up to 99%) of the presented method render these fluorinated amino acids readily available for systematic medicinal chemistry studies and de novo peptide design.
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu chong zhi Road, Shanghai 201203, People's Republic of China.
authors.forename: Jiang
authors.initials: J
authors.lastname: Wang
authors.forename: Daizong
authors.initials: D
authors.lastname: Lin
authors.forename: Shengbin
authors.initials: S
authors.lastname: Zhou
authors.forename: Xiao
authors.initials: X
authors.lastname: Ding
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Soloshonok
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
mesh_terms: D000409:Alanine / Q000737:chemistry*; D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D008024:Ligands; D009942:Organometallic Compounds; D005461:Fluorine; D000409:Alanine; D005998:Glycine