2-Hydroxyphenacyl ester: a new photoremovable protecting group.

Autor: Ngoy BP; Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00, Brno, Czech Republic., Sebej P, Solomek T, Lim BH, Pastierik T, Park BS, Givens RS, Heger D, Klán P
Jazyk: angličtina
Zdroj: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology [Photochem Photobiol Sci] 2012 Sep; Vol. 11 (9), pp. 1465-75. Date of Electronic Publication: 2012 Jul 06.
DOI: 10.1039/c2pp25133g
Abstrakt: A 2-hydroxyphenacyl moiety absorbing below 370 nm is proposed as a new photoremovable protecting group for carboxylates and sulfonates. Laser flash photolysis and steady-state sensitization studies show that the leaving group is released from a short-lived triplet state. In addition, DFT-based quantum chemical calculations were performed to determine the key reaction steps. We found that triplet excited state intramolecular proton transfer represents a major deactivation channel. Minor productive pathways involving the triplet anion and quinoid triplet enol intermediates have also been identified.
Databáze: MEDLINE