Derivatives of aminoquinones with N-protected amino acids

Abstract

SummaryThe synthesis of derivatives of aminoquinones with N-protected amino acids is reported here. 2-Amino-1,4-benzoquinone and 2-amino-l,4-naphthoquinone, prepared by the azide method in yields of 60 and 95% respectively, were coupled with N-Boc-protected amino acids including glycine, serine, proline and tyrosine, to give the correspondening derivatives. N, NI-Diisopropylcarbodiimide/1-hydroxybenzotriazole or N, N 1-dicyclohexylcarbodiimide/HOBt used as coupling reagents provided the expected products in satisfactory yields and purities as supported by TLC, HPLC and spectral analysis.

Electrochemical synthesis of amino-substituted 1,2-benzoquinone derivatives

“…In the mass spectra of compounds 5a-c, strong molecular ions [M + 2H] were recorded. This mass is related to protonation of the quinonic moiety and amino group [30,31].…”

The detection of latent fingermarks on porous surfaces using amino acid sensitive reagents: A review

“…Naphthoquinones are a class of compounds that are well known for their bioactivity [116,117] and their ability to react with amino groups have been extensively reported [115,[118][119][120][121][122][123][124][125][126][127][128][129]. 1,2-naphthoquinone-4-sulfonate has been employed for the determination of amino acids through the formation of highly coloured compounds [130][131][132][133][134].…”

Chemical and Electrochemical Syntheses of Benzo[b](1,4)‐diazepine‐7,8‐diones

“…The M + peaks of nitrogen‐containing or oxygen‐containing compounds usually show some extra mass units that are more than the exact molecular masses. It usually depends on the number of the nitrogen or oxygen in the molecule and is related to protonation of the quinonic moiety and/or amino group .…”