Synthesis of a Fluorescent‐Labeled Bisbenzamidine Containing the Central (6,7‐Dimethoxy‐4‐coumaryl)Alanine Building Block

Häußler, Daniela; Gütschow, Michael

doi:10.1002/hc.21269

Cited by 4 publications

(3 citation statements)

References 35 publications

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“…The simplicity of the coumarin scaffold (that is, 1-benzopyran-2-one) has facilitated the preparation of FlAAs integrating this fluorescent structure. Coumarinbased FlAAs can be prepared by Pechmann condensation, either between an amino acid containing a β-ketoester unit and a phenol derivative or between tyrosine and an ethyl acetoacetate derivative 79,80 . Alternatively, 7-(hydroxycoumarin-4-yl)ethylglycine is prepared by Pd-catalysed cross coupling between 2,4-dimethoxyphenylboronic acid and amino acids containing β-ketoester groups 81 .…”

Section: [H2] Non-natural Flaasmentioning

confidence: 99%

Fluorescent amino acids as versatile building blocks for chemical biology

et al. 2020

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Fluorophores have transformed the way we study biological systems, enabling noninvasive studies in cells and intact organisms, which increase our understanding of complex processes at the molecular level. Fluorescent amino acids (FlAAs) have become an essential chemical tool because they can be used to construct fluorescent macromolecules, such as peptides and proteins, without disrupting their native biomolecular properties. Fluorescent and fluorogenic amino acids with unique photophysical properties have been designed for tracking protein-protein interactions in situ or imaging nanoscopic events in real-time with high spatial resolution. In this Review, we discuss advances in the design and synthesis of FlAAs and how they have contributed to the field of chemical biology in the past 10 years. Important areas of research that we review include novel methodologies to synthesize building blocks with tunable spectral properties, their integration into peptide and protein scaffolds using sitespecific genetic encoding and bio-orthogonal approaches, and their application to design novel artificial proteins as well as to investigate biological processes in cells by means of optical imaging.

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Section: [H2] Non-natural Flaasmentioning

confidence: 99%

Fluorescent amino acids as versatile building blocks for chemical biology

et al. 2020

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“…More recently, this approach has been used to prepare various functionalised coumarin derived α-amino acids for biological imaging. [29][30][31] A phosphate derivative 10 ( Fig. 2) was prepared as a mimic of phosphotyrosine and following incorporation into cell penetrating peptides, was used to study the activity of protein tyrosine phosphatases.…”

Section: Coumarin Derived α-Amino Acidsmentioning

confidence: 99%

“…Using the Garbay approach, Häuβler and Gütschow prepared a fluorescent bisbenzamidine coumarin derivative 12, which has an emission maximum at 432 nm. 31 The authors propose that this compound could find application in the study of minor grooves of adenine/thyminerich double-strand DNA.…”

Section: Coumarin Derived α-Amino Acidsmentioning

confidence: 99%

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

Harkiss

Sutherland

2016

Org. Biomol. Chem.

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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.

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