2-Hydroxyphenacyl ester: a new photoremovable protecting group

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:

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

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)

Citovat

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.

@article{1081101,
   author = {Ngoy, Bokolombe Pitchou and Šebej, Peter and Šolomek, Tomáš and Lim, Bum Hee and Pastierik, Tomáš and Park, Bong Ser and Givens, Richard and Heger, Dominik and Klán, Petr},
   article_location = {Cambridge, UK},
   article_number = {9},
   doi = {http://dx.doi.org/10.1039/C2PP25133G},
   keywords = {Photochemistry; 2-Hydroxyphenacyl ester; photoremovable protecting group},
   language = {eng},
   issn = {1474-905X},
   journal = {Photochemical & Photobiological Sciences},
   title = {2-Hydroxyphenacyl ester: a new photoremovable protecting group},
   url = {http://pubs.rsc.org/en/content/articlelanding/2012/pp/c2pp25133g},
   volume = {11},
   year = {2012}
}

TY  - JOUR
ID  - 1081101
AU  - Ngoy, Bokolombe Pitchou - Šebej, Peter - Šolomek, Tomáš - Lim, Bum Hee - Pastierik, Tomáš - Park, Bong Ser - Givens, Richard - Heger, Dominik - Klán, Petr
PY  - 2012
TI  - 2-Hydroxyphenacyl ester: a new photoremovable protecting group
JF  - Photochemical & Photobiological Sciences
VL  - 11
IS  - 9
SP  - 1465-1475
EP  - 1465-1475
PB  - Royal Society of Chemistry
SN  - 1474905X
KW  - Photochemistry
KW  - 2-Hydroxyphenacyl ester
KW  - photoremovable protecting group
UR  - http://pubs.rsc.org/en/content/articlelanding/2012/pp/c2pp25133g
N2  - 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.
ER  -

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. \textit{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.

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