Synthesis of fluorescent dipeptidomimetics and their ribosomal incorporation into green fluorescent protein

Bioorganic & Medicinal Chemistry Letters
Sandipan Roy ChowdhurySidney M Hecht

Abstract

The synthesis and incorporation into position 66 of green fluorescent protein (GFP) by in vitro protein translation of novel oxazole and thiazole based dipeptidomimetics are described. The compounds may be regarded as GFP chromophore analogues, and are strongly fluorescent. An α-amido-β-ketoester intermediate was obtained via bisacylation of a protected glycine. The intermediate underwent dehydrative cyclization to afford the 1,3-oxazole and was treated with Lawesson's reagent to furnish the 1,3-thiazole. When these fluorophores were introduced into position 66 of GFP in place of Tyr66, the resulting GFP analogues exhibited fluorescence emission several-fold greater than wild-type GFP; the emission was also shifted to shorter wavelength. It may be noted that compared to the typical fluorophores formed in the natural and modified fluorescent proteins, the oxazole and thiazole fluorophores are completely stable and do not require activation by posttranslational modification to exhibit fluorescence.

References

Feb 11, 1994·Science·M ChalfieD C Prasher
Dec 21, 2006·Biochemistry·Larisa M DedkovaSidney M Hecht
Aug 25, 2015·Journal of the American Chemical Society·Rumit MainiSidney M Hecht

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Citations

Jan 31, 2021·Nature Communications·Haruka TsutsumiHiroaki Suga
Oct 3, 2020·Bioorganic & Medicinal Chemistry·Chao ZhangSidney M Hecht
Oct 20, 2018·The Journal of Organic Chemistry·John T PetroffRyan D McCulla
Mar 21, 2019·Journal of the American Chemical Society·Shengxi ChenSidney M Hecht
Mar 25, 2019·Journal of the American Chemical Society·Larisa M Dedkova, Sidney M Hecht

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