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Thiol‐Ene Click Reactions – Versatile Tools for the Modification of Unsaturated Amino Acids and Peptides
Author(s) -
Karmann Lisa,
Kazmaier Uli
Publication year - 2013
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.201300672
Subject(s) - chemistry , thiol , amino acid , click chemistry , ene reaction , tsuji–trost reaction , claisen rearrangement , allylic rearrangement , combinatorial chemistry , side chain , peptide , organic chemistry , alkylation , alkene , catalysis , biochemistry , polymer
Terminal γ,δ‐unsaturated amino acids, easily available by Claisen rearrangement or palladium‐catalysed allylic alkylation, are excellent substrates for radical thiol additions. These click reactions allow the introduction of highly functionalized side‐chains into a given amino acid or peptide. This protocol is suitable for the modification of all kinds of terminal alkenes, such as allyl protecting groups.