title: [Synthesis of biosynthetic precursors of red fluorescent proteins' chromophores].
abstract: A method for the synthesis of 5-arylidene-3,5-dihydro-4H-imidazol-4-ones, the corresponding chromophore of green fluorescent protein (GFP) with acylaminoalkyl substituents at position 2 of imidazole core have been developed. These structures represent biosynthetic precursors of the chromophores of red fluorescent proteins. The method is based on masking of the dehydrotyrosine fragment with beta-hydroxytyrosine moiety The key stages of the synthesis include peptide coupling of beta-hydroxytyrosine with the N-acetylamino acid of choice, unmasking of dehydrotyrosine by O-acylation with subsequent elimination, and cyclization of the obtained derivatives of 3-acylaminocinnamic acid in basic media.
authors.forename: P E
authors.initials: PE
authors.lastname: Ivashkin
authors.forename: K A
authors.initials: KA
authors.lastname: Luk'ianov
authors.forename: I V
authors.initials: IV
authors.lastname: Iampolskiĭ
mesh_terms: D000215:Acylation; D004295:Dihydroxyphenylalanine / Q000737:chemistry; D049452:Green Fluorescent Proteins / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D008164:Luminescent Proteins / Q000737:chemistry*; D000097573:Red Fluorescent Protein
chemical_list: D004295:Dihydroxyphenylalanine; D049452:Green Fluorescent Proteins; D007093:Imidazoles; D008164:Luminescent Proteins; D000097573:Red Fluorescent Protein; C117197:imidazolone