Crystal structures of amino acids: from bond lengths in glycine to metal complexes and high-pressure polymorphs

Görbitz, Carl Henrik

doi:10.1080/0889311x.2014.964229

Cited by 61 publications

(42 citation statements)

References 182 publications

(239 reference statements)

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“…Selected facets of organic crystals that have titratable sites in two-dimensional lattices [70] are one class of candidates. In particular, crystals of natural or modified amino acids can have three-dimensional lattices of possibly titratable amino and carboxyl groups, as well as side chains that can also be titratable [71], and their surfaces can be studied with use of atomic force microscopy (AFM) [72–75]. Clearly, a search for a checkerboard-type protonation pattern would then hinge in part on finding a suitable facet of such a crystal, for which the corresponding two-dimensional lattice may be approximated by a geometry similar to that modeled here.…”

Section: Further Discussion and Conclusionmentioning

confidence: 99%

Charge-regulation phase transition on surface lattices of titratable sites adjacent to electrolyte solutions: An analog of the Ising antiferromagnet in a magnetic field

Shore

Thurston

2015

Phys. Rev. E

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We report a charge-patterning phase transition on two-dimensional square lattices of titratable sites, here regarded as protonation sites, placed in a low-dielectric medium just below the planar interface between this medium and a salt solution. We calculate the work-of-charging matrix of the lattice with use of a linear Debye-Hückel model, as input to a grand-canonical partition function for the distribution of occupancy patterns. For a large range of parameter values, this model exhibits an approximate inverse cubic power-law decrease of the voltage produced by an individual charge, as a function of its in-lattice separation from neighboring titratable sites. Thus, the charge coupling voltage biases the local probabilities of proton binding as a function of the occupancy of sites for many neighbors beyond the nearest ones. We find that even in the presence of these longer-range interactions, the site couplings give rise to a phase transition in which the site occupancies exhibit an alternating, checkerboard pattern that is an analog of antiferromagnetic ordering. The overall strength W of this canonical charge coupling voltage, per unit charge, is a function of the Debye length, the charge depth, the Bjerrum length, and the dielectric coefficients of the medium and the solvent. The alternating occupancy transition occurs above a curve of thermodynamic critical points in the (pH-pK,W) plane, the curve representing a charge-regulation analog of variation of the Néel temperature of an Ising antiferromagnet as a function of an applied, uniform magnetic field. The analog of a uniform magnetic field in the antiferromagnet problem is a combination of pH-pK and W, and 1/W is the analog of the temperature in the antiferromagnet problem. We use Monte Carlo simulations to study the occupancy patterns of the titratable sites, including interactions out to the 37th nearest-neighbor category (a distance of 74 lattice constants), first validating simulations through comparison with exact and approximate results for the nearest-neighbor case. We then use the simulations to map the charge-patterning phase boundary in the (pH-pK,W) plane. The physical parameters that determine W provide a framework for identifying and designing real surfaces that could exhibit charge-patterning phase transitions.

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Section: Further Discussion and Conclusionmentioning

confidence: 99%

Charge-regulation phase transition on surface lattices of titratable sites adjacent to electrolyte solutions: An analog of the Ising antiferromagnet in a magnetic field

Shore

Thurston

2015

Phys. Rev. E

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“…Zwitterionic leucine, tryptophan, and phenylalanine form double sheet assemblies with a hydrophobic layer composed of the alkyl or aryl moieties, and a hydrophilic layer with an extended H-bond network. [8] In contrast, zwitterionic proline crystallizes in single sheets or one-dimensional tapes. [6,7] However, (4R)-4-phenyl proline, a proline derivative bearing a phenyl moiety at C(γ), crystallized into double-sheets, [9] a molecular organization reminiscent to that observed for amino acids with large hydrophobic side chains.…”

Section: Introductionmentioning

confidence: 99%

4‐Naphthylmethyl Proline Forms a Channel Structure

Foletti

Trapp

Loosli

et al. 2019

Helvetica Chimica Acta

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Proline and proline derivatives are useful tools to control the structural properties of peptides and proteins, and thereby modulate numerous processes. Here, we show that proline derivatives can have unique structural properties in the solid state by presenting the crystal structure of zwitterionic (2S,4S)/(2S,4R)‐4‐[(naphthalen‐2‐yl)methyl]proline (H‐Nap‐OH). This amphiphilic proline derivative forms a columnar structure around large hydrophilic and small hydrophobic channels with diameters of 9 Å and 4 Å, respectively. We show that this architecture, which is unprecedented for amino acids, results from the combination of a hydrogen bond network between the ammonium and carboxylate moieties and π–π as well as CH–π interactions between the aromatic moieties.

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“…In particular, it was possible to gain information on the modifications of the hydrogen bonds studying different deuterated of amino acids samples using inelastic neutron scattering [9 -11]. From these data the elastic intensity can be expressed as a function of temperature such as I(T) = I(0).exp[-Q 2 u(T) 2 ], where Q is the scattering vector and u(T) represents the mean-square displacement of the scattering nuclei. Additionally, if a dynamic transition occurs, one can observe a change in the slope of the observed u(T) 2 .…”

Section: Introductionmentioning

confidence: 99%

Application of Neutron Scattering in Amino Acid Crystals – Structural and Dynamical Information

Freire¹,

Pereira²,

Bordallo³

2016

Neutron Scattering

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In this work results oλ neutron powder diλλraction and inelastic neutron scatterinμ on aliphatic amino acid L-alanine, L-valine and L-leucine crystals are presented. The study allows inλerrinμ important inλormations about both the stability oλ the structures and the dynamics oλ phase transitions. In particular, it was possible to compare the behavior oλ diλλerent amino acids and to inλer that chanμes in the mean-square displacements observed λor two deuterated λorms oλ L-alanine ND

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Crystal structures of amino acids: from bond lengths in glycine to metal complexes and high-pressure polymorphs

Cited by 61 publications

References 182 publications

Charge-regulation phase transition on surface lattices of titratable sites adjacent to electrolyte solutions: An analog of the Ising antiferromagnet in a magnetic field

Charge-regulation phase transition on surface lattices of titratable sites adjacent to electrolyte solutions: An analog of the Ising antiferromagnet in a magnetic field

4‐Naphthylmethyl Proline Forms a Channel Structure

Application of Neutron Scattering in Amino Acid Crystals – Structural and Dynamical Information

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