Synthesis of fluorescent enone derived alpha-amino acids.
The development of a facile and general method for the preparation of enone derived alpha-amino acids is described. The key step involves a Horner-Wadsworth-Emmons reaction between an aspartic acid derived beta-keto phosphonate ester and a range of aldehydes resulting in the formation of highly functionalised alpha-amino acids in good yields. An efficient two-stage deprotection process using mild conditions was developed to give the parent alpha-amino acids. Application of this methodology has produced a novel fluorescent alpha-amino acid that has potential as a biological marker.
Fowler
Lindsay S
LS
WestCHEM, Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, UK G12 8QQ.
Ellis
David
D
Sutherland
Andrew
A
D000475:Alkenes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
D000475:Alkenes; D000596:Amino Acids; D005456:Fluorescent Dyes; D007659:Ketones