title: Synthesis and properties of a sterically unencumbered δ-silanediol amino acid.
abstract: An amino acid carrying a 1-(4-dihydroxymethylsilyl)butyl side chain has been prepared in enantiomerically pure form as a potential inhibitor of the enzyme arginase, a pharmaceutical target. As a water-soluble silanediol, this compound was anticipated to be entropically stabilized against polymerization and siloxane formation. At 50 mM in D(2)O, the degree of oligomerization was found to be pH dependent, with diastereomeric mixtures formed on condensation. Above pH 11 the silane is largely monomeric.
authors.affiliation: Department of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, Pennsylvania 19122, USA.
authors.forename: Jin Kyung
authors.initials: JK
authors.lastname: Kim
authors.forename: Scott McN
authors.initials: SM
authors.lastname: Sieburth
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D012821:Silanes; C475536:silanediol; D014867:Water