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

Acta Crystallogr C Struct Chem. 2014 Mar;70(Pt 3):326-31. doi: 10.1107/S2053229614002563. Epub 2014 Feb 22.

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 π-π stacking and hydrogen-bonding interactions are believed to form the basis of the self-assembling properties.

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

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrogen-Ion Concentration
  • Models, Molecular
  • Phenylalanine / chemistry*
  • Synchrotrons
  • X-Ray Diffraction

Substances

  • Phenylalanine