Diastereoselective synthesis of non-proteinogenic alpha-amino acids.
The synthesis of enantiomerically pure azatyrosine, tribromophenylalanine and trichlorophenylalanine is described, using two methods, diastereoselective alkylation and (or) diastereoselective protonation of chiral enolates.
Lecointe
L
L
Laboratoire d'Aminoacides, Peptides et Protéines, Université Montpellier I, France.
Rolland
V
V
Pappalardo
L
L
Roumestant
M L
ML
Viallefont
P
P
Martinez
J
J
D000409:Alanine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D002845:Chromatography; D002851:Chromatography, High Pressure Liquid; D013058:Mass Spectrometry; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
C411576:2,4,6-tribromophenylalanine; C411577:2,4,6-trichlorophenylalanine; C011870:beta-(5-hydroxy-2-pyridyl)alanine; D010649:Phenylalanine; D000409:Alanine