J 2012

2-Hydroxyphenacyl ester: a new photoremovable protecting group

NGOY, Bokolombe Pitchou, Peter ŠEBEJ, Tomáš ŠOLOMEK, Bum Hee LIM, Tomáš PASTIERIK et. al.

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

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

Impact factor

Impact factor: 2.923

RIV identification code

RIV/00216224:14310/12:00058037

Organization unit

Faculty of Science

UT WoS

000307583800008

Keywords in English

Photochemistry; 2-Hydroxyphenacyl ester; photoremovable protecting group

Tags

Tags

International impact, Reviewed
Změněno: 11/1/2013 16:57, prof. RNDr. Petr Klán, Ph.D.

Abstract

V originále

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)