A novel synthesis of enantiomerically pure 5,5,5,5',5',5'-hexafluoroleucine.
[reaction in text] A novel, short, and efficient synthesis of (S)-5,5,5,5',5',5'-hexafluoroleucine (6) in greater than 99% ee starting from the protected oxazolidine aldehyde 1 is described. The enantiomeric excess of the product was calculated from an NMR analysis of a dipeptide formed by reaction with a protected L-serine derivative. Furthermore, a racemic sample of N-acylated hexafluoroleucine was enzymatically resolved by treatment with porcine kidney acylase I and was found to have the same optical rotation as a synthetic sample of 6.
Xing
X
X
Department of Chemistry, Tufts University, 62 Talbot Avenue, Medford, Massachusetts 02155, USA.
Fichera
A
A
Kumar
K
K
D000581:Amidohydrolases / Q000378:metabolism; D004151:Dipeptides / Q000032:analysis; D007930:Leucine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012694:Serine / Q000737:chemistry; D013237:Stereoisomerism; D013936:Thymidine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
C428007:2-(N-formyl-N-methyl)aminoethyl deoxythymdine phosphoramidite; C428006:5,5,5,5',5',5'-hexafluoroleucine; D004151:Dipeptides; D012694:Serine; D000581:Amidohydrolases; C019672:aminoacylase I; D007930:Leucine; D013936:Thymidine