B. Trofimov, A. Mal’kina, O. Shemyakina
Sep 1, 2007
Citations
0
Influential Citations
8
Citations
Journal
Synthesis
Abstract
Amino acids (glycine, β-alanine, γ-aminobutyric and e-aminocapronic acids, D,L-valine, and D,L-leucine) react under biomimetic conditions (H 2 O, NaOH, pH ~8.6-9.9, room temperature) smoothly with α,β-acetylenic γ-hydroxyacid nitriles to give a novel family of unnatural amino acids containing a 5-imino-2,5-dihydro-3-furanyl substituent at the amino group, in 61-98% yield. As follows from a single-crystal X-ray analysis of 2-[(5-imino-2,2-dimethyl-2,5-dihydro-3-furanyl)amino]acetic acid, the synthesized amino acids are zwitterions with a protonated imino group in the iminodihydrofuran moiety.