title: Light-directed radial combinatorial chemistry: orthogonal safety-catch protecting groups for the synthesis of small molecule microarrays.
abstract: We describe the development of photolabile protecting groups based on the 3,4,5-trimethoxyphenacyl group (TMP). Orthogonal safety-catches were created by introducing an acid-activatible dimethyl ketal (AA-TMP) and an oxidatively activatible 1,3-dithiane (OA-TMP) into the photolabile TMP group. We demonstrate the application of these protecting groups in light-directed synthesis of small molecule microarrays with diversity elements radially attached to a hydroxyproline scaffold.
authors.affiliation: Department of Chemistry, Center for Nanotechnology, University of Wisconsin, Madison, WI 53706, USA.
authors.forename: Alex
authors.initials: A
authors.lastname: Shaginian
authors.forename: Madhusudan
authors.initials: M
authors.lastname: Patel
authors.forename: Mo-Huang
authors.initials: MH
authors.lastname: Li
authors.forename: Shane T
authors.initials: ST
authors.lastname: Flickinger
authors.forename: Changhan
authors.initials: C
authors.lastname: Kim
authors.forename: Franco
authors.initials: F
authors.lastname: Cerrina
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Belshaw
mesh_terms: D000098:Acetophenones / Q000737:chemistry*; D001573:Benzoin / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D006909:Hydroxyproline / Q000737:chemistry; D046228:Microarray Analysis / Q000379:methods*; D010782:Photolysis
chemical_list: D000098:Acetophenones; D001573:Benzoin; D006909:Hydroxyproline