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

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

Author information

1
Partnership for Structural Biology, Institut Laue-Langevin, 38042 Grenoble, France.
2
EPSAM/ISTM, Keele University, Staffordshire, ST5 5BG, England.
3
Institut Laue-Langevin, 38042 Grenoble, France.
4
Department of Molecular Microbiology and Biotechnology, Tel Aviv University, Tel Aviv 6997801, Israel.

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

PMID:
24594728
DOI:
10.1107/S2053229614002563
[Indexed for MEDLINE]
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