Light-directed radial combinatorial chemistry: orthogonal safety-catch protecting groups for the synthesis of small molecule microarrays.
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.
Shaginian
Alex
A
Department of Chemistry, Center for Nanotechnology, University of Wisconsin, Madison, WI 53706, USA.
Patel
Madhusudan
M
Li
Mo-Huang
MH
Flickinger
Shane T
ST
Kim
Changhan
C
Cerrina
Franco
F
Belshaw
Peter J
PJ
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
D000098:Acetophenones; D001573:Benzoin; D006909:Hydroxyproline