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Silole Amino Acids with Aggregation‐Induced Emission Features Synthesized by Hydrosilylation
Author(s) -
Arribat Mathieu,
Rémond Emmanuelle,
Richeter Sébastien,
Gerbier Philippe,
Clément Sébastien,
Cavelier Florine
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801869
Subject(s) - hydrosilylation , moiety , alkyne , amino acid , alkene , tripeptide , peptide , chemistry , peptide synthesis , dipeptide , alanine , amine gas treating , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , biochemistry
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 λ em ca. 500 nm and Δλ ca. 100 nm. This approach constitutes an alternative and promising strategy for incorporation of such AIE fluorogens to peptides.