Physical Sciences and Mathematics Commons^™

Novel N-Derivatized-7-Nitroindolines For The Synthesis Of Photocleavable Crosslinkers, And For Solid Phase Peptide Synthesis, Hector Patricio Del Castillo

Open Access Theses & Dissertations

7-Nitroindoline-based photochemistry has focused mostly on N-acyl-7-nitroindolines, which have been used as photocleavable protecting groups for carboxylic acids that can be efficiently removed by illumination with UV-light. They offer an alternative to the more commonly used o-nitrobenzyl-based photocleavable protecting groups. N-acyl-7-nitroindolines can also be used as photochemical acylating agents in inert solvents. For example, they have found application in peptide fragment condensation, the convergent synThesis of N-glycopeptides, and the synThesis of peptide thioesters, forming amide and thioester bonds with amine and thiol nucleophiles, respectively, under neutral conditions. The photochemical activation of N-acyl-7-nitroindolines can occur with UV light (λ = 350 …