title: A concise preparation of the fluorescent amino acid L-(7-hydroxycoumarin-4-yl) ethylglycine and extension of its utility in solid phase peptide synthesis.
abstract: Incorporation of the unnatural amino acid L-(7-hydroxycoumarin-4-yl)ethylglycine (7-HC) is a powerful and reliable approach for the preparation of fluorescently labeled proteins. The growing popularity of this valuable amino acid prompted us to pursue an improved protocol for its synthetic preparation. The optimized procedure here described provides ready access to multi-gram quantities of 7-HC. Also reported is an extension of the utility of 7-HC in the generation of a protected building block suitable for use in solid phase peptide synthesis. The building block was successfully incorporated at various positions in a series of model peptides, including analogues of the cell penetrating HIV-Tat peptide, further illustrating the utility of this unique amino acid.
authors.affiliation: Department of Medicinal Chemistry & Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, University of Utrecht, 3584 CG Utrecht, The Netherlands.
authors.forename: Timo
authors.initials: T
authors.lastname: Koopmans
authors.forename: Matthijs
authors.initials: M
authors.lastname: van Haren
authors.forename: Linda Quarles
authors.initials: LQ
authors.lastname: van Ufford
authors.forename: Jeffrey M
authors.initials: JM
authors.lastname: Beekman
authors.forename: Nathaniel I
authors.initials: NI
authors.lastname: Martin
mesh_terms: D000595:Amino Acid Sequence; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D015497:HIV-1 / Q000378:metabolism; D006367:HeLa Cells; D006801:Humans; D006863:Hydrogen-Ion Concentration; D018613:Microscopy, Confocal; D010446:Peptide Fragments / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D060327:Solid-Phase Synthesis Techniques; D014468:Umbelliferones / Q000737:chemistry*; D054322:tat Gene Products, Human Immunodeficiency Virus / Q000737:chemistry
chemical_list: C522545:(7-hydroxycoumarin-4-yl) ethylglycine; D010446:Peptide Fragments; D010455:Peptides; D014468:Umbelliferones; D054322:tat Gene Products, Human Immunodeficiency Virus; C422951:tat peptide (48-60), Human immunodeficiency virus 1; D005998:Glycine