2-Hydroxyphenacyl ester: a new photoremovable protecting group

NGOY, Bokolombe Pitchou, Peter ŠEBEJ, Tomáš ŠOLOMEK, Bum Hee LIM, Tomáš PASTIERIK, Bong Ser PARK, Richard GIVENS, Dominik HEGER and Petr KLÁN. 2-Hydroxyphenacyl ester: a new photoremovable protecting group. Photochemical & Photobiological Sciences. Cambridge, UK: Royal Society of Chemistry, 2012, vol. 11, No 9, p. 1465-1475. ISSN 1474-905X. Available from: https://dx.doi.org/10.1039/C2PP25133G.

Basic information

• Original name: 2-Hydroxyphenacyl ester: a new photoremovable protecting group
• Authors: NGOY, Bokolombe Pitchou (180 Democratic Republic of the Congo, belonging to the institution), Peter ŠEBEJ (703 Slovakia, belonging to the institution), Tomáš ŠOLOMEK (703 Slovakia, belonging to the institution), Bum Hee LIM (410 Republic of Korea), Tomáš PASTIERIK (703 Slovakia, belonging to the institution), Bong Ser PARK (410 Republic of Korea), Richard GIVENS (840 United States of America), Dominik HEGER (203 Czech Republic) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution).
• Edition: Photochemical & Photobiological Sciences, Cambridge, UK, Royal Society of Chemistry, 2012, 1474-905X.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10401 Organic chemistry
• Country of publisher: United Kingdom of Great Britain and Northern Ireland
• Confidentiality degree: is not subject to a state or trade secret
• WWW: URL
• Impact factor: Impact factor: 2.923
• RIV identification code: RIV/00216224:14310/12:00058037
• Organization unit: Faculty of Science
• Doi: http://dx.doi.org/10.1039/C2PP25133G
• UT WoS: 000307583800008
• Keywords in English: Photochemistry; 2-Hydroxyphenacyl ester; photoremovable protecting group
• Tags: AKR, rivok
• Tags: International impact, Reviewed

Abstract

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.

Links

• ED0001/01/01, research and development project: Name: CETOCOEN
• GA203/09/0748, research and development project: Name: Nové fotoaktivovatelné sloučeniny pro organickou chemii a biologii

Investor: Czech Science Foundation, New photoactivatable compounds for organic chemistry and biology

• ME09021, research and development project: Name: Vývoj nových fotoaktivovatelných systémů pro biologické studie

Investor: Ministry of Education, Youth and Sports of the CR, New photoactivatable systems for biological studies, Research and Development Programme KONTAKT (ME)