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Silole Amino Acids with Aggregation-Induced Emission Features Synthesized by Hydrosilylation

Abstract : The synthesis of silole amino acids was achieved through hydrosilylation of alkene or alkyne‐containing amino acids with 1‐methyl‐2,3,4,5‐tetraphenyl‐1H‐silole, using Karstedt's catalyst with yield up to 95 % and without epimerization. After selective deprotection of carboxylic acid or amine functions respectively, C‐ or N‐peptide coupling with an alanine moiety proved their possible incorporation into peptides. A model tripeptide was synthesized by solid phase synthesis with the N‐Fmoc protected silole amino acid version. The silole moiety can be also grafted on a precursor peptide directly on the solid support. These amino acids and peptides exhibit AIE properties with λem ca. 500 nm and Δλ ca. 100 nm. This approach constitutes an alternative and promising strategy for incorporation of such AIE fluorogens to peptides.
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Soumis le : mercredi 17 avril 2019 - 16:46:13
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Mathieu Arribat, Emmanuelle Remond, Sébastien Richeter, Philippe Gerbier, Sébastien Clément, et al.. Silole Amino Acids with Aggregation-Induced Emission Features Synthesized by Hydrosilylation. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2019, 2019 (12), pp.2275-2281. ⟨10.1002/ejoc.201801869⟩. ⟨hal-02100708⟩



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