New hydrophobic L-amino acid salts: maleates of L-leucine, L-isoleucine and L-norvaline.

Sergey G Arkhipov, Denis A Rychkov, Alexey M Pugachev, Elena V Boldyreva

Acta crystallographica. Section C, Structural chemistry 2015 Jul

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Crystals of maleates of three amino acids with hydrophobic side chains [L-leucenium hydrogen maleate, C6H14NO2(+)·C4H3O4(-), (I), L-isoleucenium hydrogen maleate hemihydrate, C6H14NO2(+)·C4H3O4(-)·0.5H2O, (II), and L-norvalinium hydrogen maleate-L-norvaline (1/1), C5H11NO2(+)·C4H3O4(-)·C5H12NO2, (III)], were obtained. The new structures contain C2(2)(12) chains, or variants thereof, that are a common feature in the crystal structures of amino acid maleates. The L-leucenium salt is remarkable due to a large number of symmetrically non-equivalent units (Z' = 3). The L-isoleucenium salt is a hydrate despite the fact that L-isoleucine is a nonpolar hydrophobic amino acid (previously known amino acid maleates formed hydrates only with lysine and histidine, which are polar and hydrophilic). The L-norvalinium salt provides the first example where the dimeric cation L-Nva...L-NvaH(+) was observed. All three compounds have layered noncentrosymmetric structures. Preliminary tests have shown the presence of the second harmonic generation (SGH) effect for all three compounds.

Citation

Sergey G Arkhipov, Denis A Rychkov, Alexey M Pugachev, Elena V Boldyreva. New hydrophobic L-amino acid salts: maleates of L-leucine, L-isoleucine and L-norvaline. Acta crystallographica. Section C, Structural chemistry. 2015 Jul;71(Pt 7):584-92