title: The self-assembling zwitterionic form of L-phenylalanine at neutral pH.
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.
authors.affiliation: Partnership for Structural Biology, Institut Laue-Langevin, 38042 Grenoble, France.
authors.forename: Estelle
authors.initials: E
authors.lastname: Mossou
authors.affiliation: EPSAM/ISTM, Keele University, Staffordshire, ST5 5BG, England.
authors.forename: Susana C M
authors.initials: SC
authors.lastname: Teixeira
authors.affiliation: EPSAM/ISTM, Keele University, Staffordshire, ST5 5BG, England.
authors.forename: Edward P
authors.initials: EP
authors.lastname: Mitchell
authors.affiliation: Institut Laue-Langevin, 38042 Grenoble, France.
authors.forename: Sax A
authors.initials: SA
authors.lastname: Mason
authors.affiliation: Department of Molecular Microbiology and Biotechnology, Tel Aviv University, Tel Aviv 6997801, Israel.
authors.forename: Lihi
authors.initials: L
authors.lastname: Adler-Abramovich
authors.affiliation: Department of Molecular Microbiology and Biotechnology, Tel Aviv University, Tel Aviv 6997801, Israel.
authors.forename: Ehud
authors.initials: E
authors.lastname: Gazit
authors.affiliation: Partnership for Structural Biology, Institut Laue-Langevin, 38042 Grenoble, France.
authors.forename: V Trevor
authors.initials: VT
authors.lastname: Forsyth
mesh_terms: D006863:Hydrogen-Ion Concentration; D008958:Models, Molecular; D010649:Phenylalanine / Q000737:chemistry*; D017356:Synchrotrons; D014961:X-Ray Diffraction
chemical_list: D010649:Phenylalanine
keywords: crystal structure; fibrils; l-phenylalanine; nanotubes; optical microscopy analysis; synchrotron radiation; zwitterion