Acta Crystallographica Section C

Crystal Structure Communications

Volume 65, Part 6 (June 2009)

organic compounds

sk3316 scheme

Acta Cryst. (2009). C65, o267-o272 [ doi:10.1107/S0108270109014309 ]

Molecular aggregation in selected crystalline 1:1 complexes of hydrophobic D- and L-amino acids. IV. The L-phenylalanine series

C. H. Görbitz, K. Rissanen, A. Valkonen and Å. Husabø

Abstract: The amino acid L-phenylalanine has been cocrystallized with D-2-aminobutyric acid, C₉H₁₁NO₂·C₄H₉NO₂, D-norvaline, C₉H₁₁NO₂·C₅H₁₁NO₂, and D-methionine, C₉H₁₁NO₂·C₅H₁₁NO₂S, with linear side chains, as well as with D-leucine, C₉H₁₁NO₂·C₆H₁₃NO₂, D-isoleucine, C₉H₁₁NO₂·C₆H₁₃NO₂, and D-allo-isoleucine, C₉H₁₁NO₂·C₆H₁₃NO₂, with branched side chains. The structures of these 1:1 complexes fall into two classes based on the observed hydrogen-bonding pattern. From a comparison with other L:D complexes involving hydrophobic amino acids and regular racemates, it is shown that the structure-directing properties of phenylalanine closely parallel those of valine and isoleucine but not those of leucine, which shares side-chain branching at C with phenylalanine and is normally considered to be the most closely related non-aromatic amino acid.

Formula: C₉H₁₁NO₂·C₄H₉NO₂, C₉H₁₁NO₂·C₅H₁₁NO₂, C₉H₁₁NO₂·C₅H₁₁NO₂S, C₉H₁₁NO₂·C₆H₁₃NO₂, C₉H₁₁NO₂·C₆H₁₃NO₂ and C₉H₁₁NO₂·C₆H₁₃NO₂


	Structure factor file (CIF format) (71.2 kbytes) [ doi:10.1107/S0108270109014309/sk3316Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (77.1 kbytes) [ doi:10.1107/S0108270109014309/sk3316IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (126.7 kbytes) [ doi:10.1107/S0108270109014309/sk3316IIIsup4.hkl ] Contains datablock III

	Structure factor file (CIF format) (69.6 kbytes) [ doi:10.1107/S0108270109014309/sk3316IVsup5.hkl ] Contains datablock IV

	Structure factor file (CIF format) (67.1 kbytes) [ doi:10.1107/S0108270109014309/sk3316Vsup6.hkl ] Contains datablock V

	Structure factor file (CIF format) (82.2 kbytes) [ doi:10.1107/S0108270109014309/sk3316VIsup7.hkl ] Contains datablock VI

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