Synthesis of fluorescent enone derived α-amino acids

Fowler, L.S., Ellis, D. and Sutherland, A. (2009) Synthesis of fluorescent enone derived α-amino acids. Organic and Biomolecular Chemistry, 7(20), pp. 4309-4316. (doi: 10.1039/b912782h)

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The development of a facile and general method for the preparation of enone derived α-amino acids is described. The key step involves a Horner–Wadsworth–Emmons reaction between an aspartic acid derived β-keto phosphonate ester and a range of aldehydes resulting in the formation of highly functionalised α-amino acids in good yields. An efficient two-stage deprotection process using mild conditions was developed to give the parent α-amino acids. Application of this methodology has produced a novel fluorescent α-amino acid that has potential as a biological marker.

Item Type:Articles
Glasgow Author(s) Enlighten ID:Sutherland, Professor Andrew
Authors: Fowler, L.S., Ellis, D., and Sutherland, A.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic and Biomolecular Chemistry
ISSN (Online):1477-0539

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