Acta Crystallographica Section C

Structural Chemistry

Volume 70, Part 3 (March 2014)

organic compounds

sk3518 scheme

Acta Cryst. (2014). C70, 326-331    [ doi:10.1107/S2053229614002563 ]

The self-assembling zwitterionic form of L-phenyl­alanine at neutral pH

E. Mossou, S. C. M. Teixeira, E. P. Mitchell, S. A. Mason, L. Adler-Abramovich, E. Gazit and V. T. Forsyth

Abstract: The title zwitterion (2S)-2-aza­niumyl-1-hy­droxy-3-phenyl­pro­pan-1-olate, C9H11NO2, also known as L-phenyl­alanine, was characterized using synchrotron X-rays. It crystallized in the monoclinic space group P21 with four mol­ecules in the asymmetric unit. The 0.62 Å resolution structure is assumed to be closely related to the fibrillar form of phenylalanine, as observed by electron microscopy and electron diffraction. The structure exists in a zwitterionic form in which [pi]-[pi] stacking and hydrogen-bonding inter­actions are believed to form the basis of the self-assembling properties.

CCDC reference: 985094

Formula: C9H11NO2

Keywords: crystal structure; synchrotron radiation; zwitterion; L-phenyl­alanine; fibrils; nanotubes; optical microscopy analysis.

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