title: Enantiomers of a selective gelatinase inhibitor: (R)- and (S)-2-[(4-phenoxyphenyl)sulfonylmethyl]thiirane.
abstract: The compound 2-[(4-phenoxyphenyl)sulfonylmethyl]thiirane, C15H14O3S2, a selective gelatinase inhibitor, was synthesized and structurally characterized. Two crystals were analyzed, one each for the R and S enantiomers, and the results were compared with the previously reported structure of the racemate. The enantiomerically pure compounds both crystallize with Z' = 2 in the space group P2₁, while the racemic mixture crystallizes with Z' = 1 in the space group P2₁/c, with disorder in the position of the thiirane group. This disorder accommodates both molecules for each of the enantiomerically pure crystals, showing good overlap of the molecules of the pure enantiomorphs with the components of the centrosymmetric structure.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA.
authors.forename: Mijoon
authors.initials: M
authors.lastname: Lee
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA.
authors.forename: Dusan
authors.initials: D
authors.lastname: Hesek
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA.
authors.forename: Bruce C
authors.initials: BC
authors.lastname: Noll
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA.
authors.forename: Allen G
authors.initials: AG
authors.lastname: Oliver
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA.
authors.forename: Shahriar
authors.initials: S
authors.lastname: Mobashery
mesh_terms: D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D061965:Matrix Metalloproteinase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C000596736:2-((4-phenoxyphenyl)sulfonylmethyl)thiirane; D004791:Enzyme Inhibitors; D061965:Matrix Metalloproteinase Inhibitors; D013450:Sulfones
keywords: MMPs; crystal structure; disorder; enantiomers; gelatinase inhibitors; matrix metalloproteinases; thiirane