Peptide Synthesis Based on t-Boc Chemistry and Solution Photogenerated Acids

Solution reactions using photogenerated reagents (PGRs) (Gao, X.; Yu, P. Y.; Leproust, E.; Sonigo, L.; Pellois, J. P.; Zhang, H. J. Am. Chem. Soc. 1998, 120, 12698) are developed for parallel synthesis of addressable, combinatorial molecular microarrays. To advance the PGR chemistry for general chemical conversions, light-controlled synthesis of peptides, which employs photogenerated acids (PGAs) and/or in combination with photosensitizers for deprotection of N-t-Boc group, is demonstrated. These reactions were performed on resin and glass plates and conveniently monitored by HPLC analysis (reactions on resin) and fluorescence emission after coupling the deprotected NH(2) group with 4(5)-carboxyfluorescein. These results demonstrate the potential of the PGA chemistry for parallel synthesis of addressable peptide libraries on a microarray platform.