“…69 We also prepared fluorescent peptides on solid phase by acylation with benzotriazole-activated derivatives of (i) coumarin-3-carboxylic acid and 7-methoxycoumarin-4acetic acid, and (ii) coumarin-3-ylcarbonyl (Cc)-and 7methoxycoumarin-4-ylacetyl (Mca)-labeled lysines. 70 The fluorescent peptides were obtained under microwave irradiation in 18-45% purified yield (Scheme 13 and Table 13). Absorption and fluorescence wavelength maxima were measured for all synthesized fluorescent peptides.…”
Section: Fluorescent Amino Acids and Peptidesmentioning
N-(Protected a-aminoacyl)benzotriazoles are efficient intermediates for N-and O-aminoacylation. These intermediates enable fast preparations of biologically relevant peptides and peptide conjugates in high yields and purity, under mild reaction conditions, with full retention of the original chirality. The developed methodology allows simple solution-and solid-phase preparative techniques to generate complex peptides and peptide conjugates and serves as a platform for generating diverse medicinal chemistry building block libraries involving amino acid and heterocyclic moieties crucial for drug development.
“…69 We also prepared fluorescent peptides on solid phase by acylation with benzotriazole-activated derivatives of (i) coumarin-3-carboxylic acid and 7-methoxycoumarin-4acetic acid, and (ii) coumarin-3-ylcarbonyl (Cc)-and 7methoxycoumarin-4-ylacetyl (Mca)-labeled lysines. 70 The fluorescent peptides were obtained under microwave irradiation in 18-45% purified yield (Scheme 13 and Table 13). Absorption and fluorescence wavelength maxima were measured for all synthesized fluorescent peptides.…”
Section: Fluorescent Amino Acids and Peptidesmentioning
N-(Protected a-aminoacyl)benzotriazoles are efficient intermediates for N-and O-aminoacylation. These intermediates enable fast preparations of biologically relevant peptides and peptide conjugates in high yields and purity, under mild reaction conditions, with full retention of the original chirality. The developed methodology allows simple solution-and solid-phase preparative techniques to generate complex peptides and peptide conjugates and serves as a platform for generating diverse medicinal chemistry building block libraries involving amino acid and heterocyclic moieties crucial for drug development.
“…A few methods to incorporate fluorescent tags in peptide libraries have been described. Rademann and co-workers optimized the preparation of fluorescein-labeled peptides, whereas Ellman’s and Katritzky’s laboratories worked on coumarin derivatives. , Unnatural amino acids containing fluorogenic motifs or FRET pairs , are useful tools but are rather used to study protein–protein interactions than to develop fluorescent probes. Split-and-mix libraries of fluorescent peptides have been also reported as optical encoding tools …”
“…Fluorescent peptides can be prepared by incorporating unnatural amino acids including a reporter (e.g., fluorogenic, solvatochromic) that is compatible with solidphase peptide synthesis protocols. [16][17][18] These approaches impart a minor change in the peptide structure, but require some prior knowledge of the residue within the sequence that can be modified without altering the properties of the peptide. More versatile strategies have been devised by loading a fluorophore (e.g., coumarin, fluorescein) as the C-terminal amino acid and building the rest of the peptide afterward.…”
Section: Solid-phase Approaches In Fluorescent Labelingmentioning
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