School of Chemistry - Research Publications

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Author: White, Jonathan × Author: Williams, Spencer × End date: 2022 × Start date: 2020 ×

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    Synthesis of the Alkylsulfonate Metabolites Cysteinolic Acid, 3-Amino-2-hydroxypropanesulfonate, and 2,3-Dihydroxypropanesulfonate
    Burchill, L ; Zudich, L ; van der Peet, PL ; White, JM ; Williams, SJ (AMER CHEMICAL SOC, 2022-03-18)
    Chiral hydroxy- and aminohydroxysulfonic acids are widespread in the marine and terrestrial environment. Here we report simple methods for the synthesis of d- and l-cysteinolic acid (from (Boc-d-Cys-OH)2 and (Boc-l-Cys-OH)2, respectively), R- and S-3-amino-2-hydroxypropanesulfonate (from S- and R-epichlorohydrin, respectively), and R- and S-2,3-dihydroxypropanesulfonate (from S- and R-epichlorohydrin, respectively). d-Cysteinolate bile salts were generated by coupling with cholic and chenodeoxycholic acids. A series of single-crystal 3D X-ray structures confirmed the absolute configurations of the aminosulfonates. By comparison of optical rotation, we assign naturally occurring 3-amino-2-hydroxypropanesulfonate from Gateloupia livida as possessing the R-configuration. This simple synthetic approach will support future studies of the occurrence, chemotaxonomic distribution, and metabolism of these alkylsulfonates.
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    Synthesis and structure of clozapine N-oxide hemi(hydrochloride): an infinite hydrogen-bonded poly[n]catenane
    van der Peet, PL ; Joyce, RD ; Ott, H ; Marcuccio, SM ; White, JM ; Williams, SJ (INT UNION CRYSTALLOGRAPHY, 2022-10)
    The structure of the title compound, 2C18H19ClN4O·HCl or (CNO)2·HCl (C36H39Cl3N8O2), at 100 K has tetra-gonal (I4/m) symmetry. The dihedral angle between the benzene rings of the fused ring system of the CNO mol-ecule is 40.08 (6)° and the equivalent angle between the seven-membered ring and its pendant N-oxide ring is 31.14 (7)°. The structure contains a very strong, symmetrical O-H⋯O hydrogen bond [O⋯O = 2.434 (2) Å] between two equivalent R 3N+-O- moieties, which share a proton lying on a crystallographic twofold rotation axis. These units then form a (CNO)4·(HCl)2 ring by way of two equivalent N-H⋯Cl hydrogen bonds (Cl- site symmetry m). These rings are catenated into infinite chains propagating along the c-axis direction by way of shape complementarity and directional C-H⋯N and C-H⋯π inter-actions.