1246619-67-9Relevant academic research and scientific papers
Chemo-, regio- and stereospecific synthesis of unnatural, fluorescent amino acids by condensation of l-lysine and 1-vinylpyrrole-2-carbaldehydes
Ivanov, Andrey V.,Ushakov, Igor A.,Petrushenko, Konstantin B.,Mikhaleva, Al'bina I.,Trofimov, Boris A.
, p. 4554 - 4558 (2010)
A new family of unnatural, optically active amino acids containing the pyrrole moiety have been synthesized by condensation of 1-vinylpyrrole-2- carbaldehydes with L-lysine under mild conditions (EtOH, room temp., 2.5-3 h, 0.5 wt.-% of CF3CO2H) in up to 90% yields. Unlike non-vinylated analogues, 1-vinylpyrrole-2-carbaldehydes react chemo-, regio- and stereospecifically with an ε-amino group only to afford products of exclusively (E) configuration. The amino acids synthesized containing aromatic or condensed aromatic substitutents in the pyrrole ring fluoresce in the UV/Vis region (γmax = 350-382 nm, Stokes shifts 6150-7800 cm -1).
