Recent advances in the synthesis and application of fluorescent α-amino acids

Abstract

Fluorescence spectroscopy has become a powerful technique for probing a range of complex biological processes including enzyme mechanisms and protein-protein interactions. While the application of this technique uses a number of strategies, many of these rely on the use of fluorescent α-amino acids. This review highlights the recent synthetic methods developed for the incorporation of highly conjugated chromophores into the side-chain of α-amino acids and the application of these compounds as probes for imaging in medicine and biology. In particular, the design and synthesis of α-amino acids bearing coumarin, flavone and polyaromatic derived chromophores is described.

Full color palette of fluorescentd-amino acids for in situ labeling of bacterial cell walls

“…Fluorescent l -amino acids have found use in peptide synthesis. 44 More importantly, encoding brighter, red-shifted, yet still relatively small fluorescent amino acids (such as the l -enantiomer of Atto 610 ADA), into proteins could be possible with the availability of new technologies, which in turn would address current issues with utilizing fluorescent protein fusions such as size and maturation. 45 As we have demonstrated, fluorescent d -amino acids serve as ideal PG probes to elucidate bacterial cell growth and division in high spatiotemporal resolution, 14 , 24 or to simply label bacterial cell surfaces for a variety of other applications in diverse bacteria.…”

4‐Aminophthalimide Amino Acids as Small and Environment‐Sensitive Fluorescent Probes for Transmembrane Peptides

“…Fluorescent amino acids should permit insights not only into fundamental behavior of peptides and proteins, but also into their localization in cellular contexts . Solvatochromic fluorophores are required for this task, due to their responses to changes in surrounding polarity .…”

“… Compound 1 is an amino acid with a chromophore side chain that is very small in relation to other common fluorophores and nearly isosteric to that of the natural tryptophan. Unlike tryptophan, which needs to be excited in the UV‐B range and shows only weak fluorescence, however, 1 can be excited at the edge of the visible light range (outside the biopolymer absorbance range) and shows bright fluorescence through a large apparent Stokes shift. Also, the more recently published 4‐cyanotryptophan meets these criteria only as a FRET donor …”

Coumarins into Polyurethanes for Smart and Functional Materials

“…From the first described synthesis of the coumarin nucleus in 1868 through the Perkin reaction, synthetical coumarins can be obtained by different methods including the aforementioned Perkin reaction, the Pechman reaction, Reformatsky reaction, Claisen reaction, Witting reaction, the Ringclosing methathesis reaction, Knovenegal reaction, and some other variations incorporating microwave assistance or applying sonochemistry, among others [8][9][10][11][12][13][14][15].…”