Crystal structure of methyl (S)-2-{(R)-4-[(tert-butoxycarbonyl)amino]-3-oxo-1,2-thiazolidin-2-yl}-3-methylbutanoate: a chemical model for oxidized protein tyrosine phosphatase 1B (PTP1B)

• Main Authors: Kasi Viswanatharaju Ruddraraju, Roman Hillebrand, Charles L. Barnes, Kent S. Gates
• Format: Article
• Language: English
• Published: International Union of Crystallography 2015-07-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; isothiazolidine-3-one derivative; oxidized PTP1B; sulfenyl amide; hydrogen bonding
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989015010051

The asymmetric unit of the title compound, C14H24N2O5S, contains two independent molecules (A and B). In each molecule, the isothiazolidin-3-one ring adopts an envelope conformation with the methylene C atom as the flap. In the crystal, the A molecules are linked to one another by N—H...O hydrogen bonds, forming columns along [010]. The B molecules are also linked to one another by N—H...O hydrogen bonds, forming columns along the same direction, i.e. [010]. Within the individual columns, there are also C—H...S and C—H...O hydrogen bonds present. The columns of A and B molecules are linked by C—H...O hydrogen bonds, forming sheets parallel to (10-1). The absolute structure was determined by resonant scattering [Flack parameter = 0.00 (3)].