Mannich N-Indolylmethylation of Amino Acids

Abstract Unprotected amino acids and simple peptides (2 examples) with free amino groups are N -indol-3-ylmethylated by a combination of paraformaldehyde or formalin and indole in aqueous ethanol at temperatures from 55–75 °C. Secondary amine incorporating amino acids and primary amine functionalize...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2017-05, Vol.49 (10), p.2257-2265
Main Authors: Wiedemann, Michael, Altmann, Philipp J., Hintermann, Lukas
Format: Article
Language:English
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Summary:Abstract Unprotected amino acids and simple peptides (2 examples) with free amino groups are N -indol-3-ylmethylated by a combination of paraformaldehyde or formalin and indole in aqueous ethanol at temperatures from 55–75 °C. Secondary amine incorporating amino acids and primary amine functionalized α-branched amino acids give rise to N -monoalkylation products, whereas unbranched primary amine functionalized amino acids and alanine give N , N -dialkylated products. The modified amino acids are amenable to amide coupling. Other electron-rich (hetero)aromatic cores besides indole (pyrrole, naphthol) are also selectively aminomethylated by amino acids and formaldehyde.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1588934