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A pseudouridine isoxazolidinyl nucleoside analogue structural analysis: a morphological approach

DOI: 10.3390/molecules23123381 DOI Help

Authors: Giuseppe Floresta (Università di Catania) , Venerando Pistarà (Università di Catania) , Kirsten E. Christensen (University of Oxford) , Emanuele Amata (Università di Catania) , Agostino Marrazzo (Università di Catania) , Davide Gentile (Università di Catania) , Antonio Rescifina (Università di Catania) , Francesco Punzo (Università di Catania)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Molecules , VOL 23

State: Published (Approved)
Published: December 2018

Open Access Open Access

Abstract: An in silico study has been conducted upon (3′RS,5′SR)-5-[2′-benzyl-5′-hydroxymethyl-1′,2′-isoxazolidin-3′-yl]uracil through a molecular dynamics/docking approach that highlights its potential inhibitory activity upon the wild-type pseudouridine 5′-monophosphate glycosidase. The crystal structure of this compound has been solved by means of X-ray single crystal diffraction and the data inferred were used to predict its crystal morphology. These data were compared with optical microscopy images and confirmed the validity of the computed models. This robust approach, already used for several other different compounds, provides a fast and reliable tool to standardize a crystallization method in order to get similar and good quality crystals. As different crystal shapes could be associated with different polymorphic forms, this method could be considered a fast and cheap screening to choose among different and coexistent polymorphic forms. Furthermore, a match with the original crystal structure of pseudouridine 5′-monophosphate is provided.

Journal Keywords: pseudouridine; pseudouridine 5′-monophosphate glycosidase; isoxazolidine analogs; crystal morphology; polymorphic forms

Subject Areas: Chemistry


Instruments: I19-Small Molecule Single Crystal Diffraction

Documents:
molecules-23-03381-v2.pdf