Structure and conformation of orthorhombic <scp>L</scp>-cysteine

Kerr, K. Ann; Ashmore, Jason

doi:10.1107/s0567740873006217

Cited by 87 publications

(63 citation statements)

References 6 publications

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“…As is visible in Figure 3 for P H conformer interaction through sulfur atom, NH 3 + and COO -groups are possible, while for P N and P C only two functional groups may interact simultaneously with the metal surface. The P H conformer (gauche) is merely found in orthorhombic crystal, 18 while both P H and P N conformers are found in the monoclinic crystal. 19 The 689 cm -1 band observed in the normal Raman spectrum of orthorhombic form was ascribed to the P H conformer, and the 735 cm -1 feature additionally observed for monoclinic crystals was ascribed to the P N rotamer.…”

Section: Resultsmentioning

confidence: 99%

Adsorption of Enantiomeric and Racemic Cysteine on a Silver Electrode − SERS Sensitivity to Chirality of Adsorbed Molecules

Graff

Bukowska

2005

J. Phys. Chem. B

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The adsorption of both (L-and D-) enantiomeric forms of cysteine on the silver electrode surface was studied by surface-enhanced Raman scattering spectroscopy (SERS) as a function of electrode potential and pH value of the solution. It was demonstrated that at potentials more positive than -0.7 V (for pH 3) or -0.8 V (for pH 2 or lower), in acidic environment L-cysteine molecules are adsorbed mainly as P H (gauche) conformer, in zwitterionic form with the COO -groups close to the surface. At more negative potentials, NH 3 + groups deprotonate at the surface with simultaneous weakening of the interaction of the carboxylic groups with the surface. Spectroscopic evidence for at least partial protonation of the COO -groups at strongly acidic solutions was given by observing the CdO stretching band at frequency lowered by about 30 cm -1 in comparison with that observed for crystalline cysteine hydrochloride. It points to the considerable enhancement of the strength of hydrogen bonds and may be ascribed to the formation of cyclic L-cysteine dimers at the electrode surface. In neutral and alkaline solutions, adsorbed L-cysteine molecules have deprotonated amino groups at wide potential range. Similar spectroelectrochemical experiments were performed for D-cysteine and for a racemic mixture of D,L-cysteine. As expected, results for D-cysteine were similar to those for L-cysteine. However, for racemic mixture at acidic pH, the spectral effects corresponding to potential-induced transition from adsorbed zwitterions to neutral molecule were considerably smaller. This effect was discussed in terms of stereoselective dimerization of cysteine molecule at the electrode surface.

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Section: Resultsmentioning

confidence: 99%

Adsorption of Enantiomeric and Racemic Cysteine on a Silver Electrode − SERS Sensitivity to Chirality of Adsorbed Molecules

Graff

Bukowska

2005

J. Phys. Chem. B

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“…Additionally, several polymorphic forms have been reported for both compounds. L-cysteine crystallizes in the monoclinic and orthorhombic forms and has been structurally characterized [53,54]. Phase transitions have been detected when lowering the temperatures [55] and also when decreasing pressures up to 4.2 GPa and decreasing to 1-7 GPa [56].…”

Section: Sulfur Amino Acids and Cysteine Cathepsinsmentioning

confidence: 99%

Thermal Analysis of Sulfur and Selenium Compounds with Multiple Applications, Including Anticancer Drugs

Plano¹,

Palop²,

Sanmartín³

2013

Applications of Calorimetry in a Wide Context - Differential Scanning Calorimetry, Isothermal Titration Calorimetry and Microca

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“…L-Cysteine crystallizes in the monoclinic and orthorhombic forms and has been structurally characterized by X-ray [8][9][10] and neutron [11] diffraction methods at ambient and low temperatures [12][13][14] as well as at ambient and higher pressures [15]. Phase transitions have been detected when lowering the temperature (ca.…”

Section: Introductionmentioning

confidence: 99%

“…Structural data for the polymorphic forms of L-cysteine and L-cystine was obtained from the Cambridge Structural Database [32] (CSD refcodes: LCYSTN to LCYSTN36 for L-cysteine [8][9][10][11][12][13][14][15] and LCYSTI10 to LCYSTI13 for L-cystine [16][17][18][19]). The PLATON [33] (as incorporated into the WinGX package [34]) and XPowder [35] software were used to prepare material for visualization and analysis.…”

Section: X-ray Diffraction Studiesmentioning

confidence: 99%

Thermal behavior and polymorphism in medium–high temperature range of the sulfur containing amino acids l-cysteine and l-cystine

Foces‐Foces

Roux

Notario

et al. 2011

J Therm Anal Calorim

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A thermophysical study of the sulfur containing amino acids L-cysteine and L-cystine has been carried out by differential scanning calorimetry (DSC). Heat capacities of both compounds were measured in the temperature interval from T = 268 K to near their respective melting temperatures. DSC and variable temperature powder X-ray diffraction analysis (PXRD) gave evidence for a solid-solid phase transition close to the melting point only in the L-cysteine sample. DSC experiments show that this solidsolid transition is not reversible in the temperature interval T = 235-485 K and presents a behavior depending on heating temperature, time, and rate. This behavior is also supported by variable-temperature PXRD. The patterns for the commercial samples, at room temperature, are consistent with those simulated for the orthorhombic and hexagonal polymorphic forms from the single-crystal X-ray analysis.

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Structure and conformation of orthorhombic L-cysteine

Cited by 87 publications

References 6 publications

Adsorption of Enantiomeric and Racemic Cysteine on a Silver Electrode − SERS Sensitivity to Chirality of Adsorbed Molecules

Adsorption of Enantiomeric and Racemic Cysteine on a Silver Electrode − SERS Sensitivity to Chirality of Adsorbed Molecules

Thermal Analysis of Sulfur and Selenium Compounds with Multiple Applications, Including Anticancer Drugs

Thermal behavior and polymorphism in medium–high temperature range of the sulfur containing amino acids l-cysteine and l-cystine

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