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

Estelle Mossou; Susana C.M. Teixeira; Edward P. Mitchell; Sax A. Mason; Lihi Adler-Abramovich; Ehud Gazit; V. Trevor Forsyth

doi:10.1107/S2053229614002563

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

Estelle Mossou
, Susana C.M. Teixeira
, Edward P. Mitchell
, Sax A. Mason
, Lihi Adler-Abramovich
, Ehud Gazit
, V. Trevor Forsyth

Tel Aviv University

Research output: Contribution to journal › Article › peer-review

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 0.62Å 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.

Original language	English
Pages (from-to)	326-331
Number of pages	6
Journal	Acta crystallographica. Section C, Structural chemistry
Volume	70
Issue number	3
DOIs	https://doi.org/10.1107/S2053229614002563
State	Published - Mar 2014

Keywords

crystal structure
fibrils
l-phenylalanine
nanotubes
optical microscopy analysis
synchrotron radiation
zwitterion

ASJC Scopus subject areas

Condensed Matter Physics
Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1107/S2053229614002563

Cite this

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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{\AA} 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.",

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doi = "10.1107/S2053229614002563",

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volume = "70",

pages = "326--331",

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T1 - The self-assembling zwitterionic form of l-phenylalanine at neutral pH

AU - Mossou, Estelle

AU - Teixeira, Susana C.M.

AU - Mitchell, Edward P.

AU - Mason, Sax A.

AU - Adler-Abramovich, Lihi

AU - Gazit, Ehud

AU - Forsyth, V. Trevor

PY - 2014/3

Y1 - 2014/3

N2 - 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 0.62Å 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.

AB - 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 0.62Å 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.

KW - crystal structure

KW - fibrils

KW - l-phenylalanine

KW - nanotubes

KW - optical microscopy analysis

KW - synchrotron radiation

KW - zwitterion

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DO - 10.1107/S2053229614002563

M3 - Article

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JO - Acta crystallographica. Section C, Structural chemistry

JF - Acta crystallographica. Section C, Structural chemistry

IS - 3

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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