Pressure induced phase transitions in the tripeptide glutathione to 5.24 GPa: the crystal structure of glutathione-II at 2.94 GPa and glutathione-III at 3.70 GPa

Stefanowicz, Fiona; Lennie, Alistair R.; Morrison, Carole A.; Richardson, Patricia; Warren, John E.

doi:10.1039/c001254h

Cited by 16 publications

(18 citation statements)

References 29 publications

(47 reference statements)

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“…7 Other transitions have been observed in L-serine, 9-14 L-cysteine, 15 DL-cysteine, 16 serine hydrate 17 and the tripeptide glutathione. 18 By contrast to the other polymorphs of glycine, the a-phase does not undergo any transitions at all, even, according to Raman spectra, up to 20 GPa. 19 Alanine (Fig.…”

Section: Introductionmentioning

confidence: 92%

Alanine at 13.6 GPa and its pressure-induced amorphisation at 15 GPa

2011

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Section: Introductionmentioning

confidence: 92%

Alanine at 13.6 GPa and its pressure-induced amorphisation at 15 GPa

2011

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“…Pressure-mediated transformations without the destruction or dissolution of the crystal are rare but can be achieved for molecules with conformational flexibility. 81 Single crystal-to-single crystal transformations have been achieved for other organic molecules through conformational changes, e.g ., β-glycine to δ-glycine, 82 glutathione-I to glutathione-II, 58 and di-p-tolyl disulfide α form to β form. 83 In the present case, this transformation results in a conformational change such that the structure closely matches the predicted conformer D. Structural overlay ( Figure S4 ) confirms that this new form corresponds to the predicted global lattice energy minimum structure of IPN.…”

Section: Resultsmentioning

confidence: 99%

“…Data collections of crystals in DACs are poor at locating H atom positions due to shading by the gasket and DAC, which reduces the completeness of the data set. 58 − 60 …”

Section: Experimental Methodsmentioning

confidence: 99%

Minimizing Polymorphic Risk through Cooperative Computational and Experimental Exploration

et al. 2020

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We combine state-of-the-art computational crystal structure prediction (CSP) techniques with a wide range of experimental crystallization methods to understand and explore crystal structure in pharmaceuticals and minimize the risk of unanticipated late-appearing polymorphs. Initially, we demonstrate the power of CSP to rationalize the difficulty in obtaining polymorphs of the well-known pharmaceutical isoniazid and show that CSP provides the structure of the recently obtained, but unsolved, Form III of this drug despite there being only a single resolved form for almost 70 years. More dramatically, our blind CSP study predicts a significant risk of polymorphism for the related iproniazid. Employing a wide variety of experimental techniques, including high-pressure experiments, we experimentally obtained the first three known nonsolvated crystal forms of iproniazid, all of which were successfully predicted in the CSP procedure. We demonstrate the power of CSP methods and free energy calculations to rationalize the observed elusiveness of the third form of iproniazid, the success of high-pressure experiments in obtaining it, and the ability of our synergistic computational-experimental approach to “de-risk” solid form landscapes.

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“…Data collections of crystals in DACs is poor at locating H-atom positions due to shading by the gasket and DAC, which reduces the completeness of the dataset. [54][55][56] Novel polymorphs of iproniazid Forms I and II were produced by slow cooling and Form III was produced by high-pressure experiments. A more detailed analysis of these novel forms, as well details on gelator synthesis, characterization methods and computational processes (molecular conformer generation, Space group selection for structure generation and structure minimization) and further results of the free energy calculations are all available in the ESI.…”

Section: High-pressure Experimentsmentioning

confidence: 99%

“…76 Single crystal-to-single crystal transformations have been achieved for other organic molecules through conformational changes, e.g. β-glycine to δglycine, 77 glutathione-I to glutathione-II, 54 and di-p-tolyl disulphide α form to β form. 78 In the present case this transformation results in a conformational change such that the structure closely matches the predicted conformer D. Structural overlay (Fig.…”

Section: High-pressure Experimentsmentioning

confidence: 99%

Minimizing Polymorphic Risk Through Cooperative Computational and Experimental Exploration

Taylor¹,

Mulvee²,

Perenyi³

et al. 2020

Preprint

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<div> <p>We combine state-of-the-art computational crystal structure prediction (CSP) techniques with a wide range of experimental crystallization methods to understand and explore crystal structure in pharmaceuticals and minimize the risk of unanticipated late-appearing polymorphs. Initially, we demonstrate the power of CSP to rationalize the difficulty in obtaining polymorphs of the well-known pharmaceutical isoniazid and show that CSP provides the structure of the recently discovered, but unsolved, Form III of this drug despite there being only a single known form for almost 70 years. More dramatically, our blind CSP study predicts a significant risk of polymorphism for the related iproniazid. Employing a wide variety of experimental techniques, including high-pressure experiments, we experimentally obtained the first three known non-solvated crystal forms of iproniazid, all of which were successfully predicted in the CSP procedure. We demonstrate the power of CSP methods and free energy calculations to rationalize the observed elusiveness of the third form of iproniazid, the success of high-pressure experiments in obtaining it, and the ability of our synergistic computational-experimental approach to “de-risk” solid form landscapes.</p> </div>

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Pressure induced phase transitions in the tripeptide glutathione to 5.24 GPa: the crystal structure of glutathione-II at 2.94 GPa and glutathione-III at 3.70 GPa

Cited by 16 publications

References 29 publications

Alanine at 13.6 GPa and its pressure-induced amorphisation at 15 GPa

Alanine at 13.6 GPa and its pressure-induced amorphisation at 15 GPa

Minimizing Polymorphic Risk through Cooperative Computational and Experimental Exploration

Minimizing Polymorphic Risk Through Cooperative Computational and Experimental Exploration

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