A 'photorelease, catch and photorelease' strategy for
bioconjugation utilizing a p-hydroxyphenacyl group

J 2016

A 'photorelease, catch and photorelease' strategy for bioconjugation utilizing a p-hydroxyphenacyl group

MADEA, Dominik, Tomáš SLANINA and Petr KLÁN

Basic information

Original name

A 'photorelease, catch and photorelease' strategy for bioconjugation utilizing a p-hydroxyphenacyl group

Authors

MADEA, Dominik (203 Czech Republic, belonging to the institution), Tomáš SLANINA (203 Czech Republic, belonging to the institution) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

Chemical communications, Cambridge, Royal Society of Chemistry, 2016, 1359-7345

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: 6.319

RIV identification code

RIV/00216224:14310/16:00088608

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1039/c6cc07496k

UT WoS

000387025600026

Keywords in English

PHOTOREMOVABLE PROTECTING GROUPS; CLICK CHEMISTRY; BIOORTHOGONAL CHEMISTRY; AMINO-ACIDS; RELEASE; PROTEINS; PHOTOTRIGGERS; BINDING; CELLS; PHOTOCHEMISTRY

Abstract

V originále

A bioorthogonal 'catch and photorelease' strategy, which combines alkyne-azide cycloaddition between p-hydroxyphenacyl azide and alkyne derivatives to form a 1,2,3-triazole adduct and subsequent photochemical release of the triazole moiety via a photo-Favorskii rearrangement, is introduced. The first step can also involve photo-release of a strained alkyne and its Cu-free click reaction with azide.

Links

GA13-25775S, research and development project

Name: Vývoj viditelným světlem aktivovatelných skupin a fluorescenčních značek pro chemii a biologii

Investor: Czech Science Foundation

LM2015051, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX RI)

Investor: Ministry of Education, Youth and Sports of the CR

LO1214, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

MADEA, Dominik, Tomáš SLANINA and Petr KLÁN. A 'photorelease, catch and photorelease' strategy for bioconjugation utilizing a p-hydroxyphenacyl group. Chemical communications. Cambridge: Royal Society of Chemistry, 2016, vol. 52, No 87, p. 12901-12904. ISSN 1359-7345. Available from: https://dx.doi.org/10.1039/c6cc07496k.

@article{1369914,
   author = {Madea, Dominik and Slanina, Tomáš and Klán, Petr},
   article_location = {Cambridge},
   article_number = {87},
   doi = {http://dx.doi.org/10.1039/c6cc07496k},
   keywords = {PHOTOREMOVABLE PROTECTING GROUPS; CLICK CHEMISTRY; BIOORTHOGONAL CHEMISTRY; AMINO-ACIDS; RELEASE; PROTEINS; PHOTOTRIGGERS; BINDING; CELLS; PHOTOCHEMISTRY},
   language = {eng},
   issn = {1359-7345},
   journal = {Chemical communications},
   title = {A 'photorelease, catch and photorelease' strategy for bioconjugation utilizing a p-hydroxyphenacyl group},
   url = {http://pubs.rsc.org/en/Content/ArticleLanding/2016/CC/C6CC07496K#!divAbstract},
   volume = {52},
   year = {2016}
}

TY  - JOUR
ID  - 1369914
AU  - Madea, Dominik - Slanina, Tomáš - Klán, Petr
PY  - 2016
TI  - A 'photorelease, catch and photorelease' strategy for bioconjugation utilizing a p-hydroxyphenacyl group
JF  - Chemical communications
VL  - 52
IS  - 87
SP  - 12901-12904
EP  - 12901-12904
PB  - Royal Society of Chemistry
SN  - 13597345
KW  - PHOTOREMOVABLE PROTECTING GROUPS
KW  - CLICK CHEMISTRY
KW  - BIOORTHOGONAL CHEMISTRY
KW  - AMINO-ACIDS
KW  - RELEASE
KW  - PROTEINS
KW  - PHOTOTRIGGERS
KW  - BINDING
KW  - CELLS
KW  - PHOTOCHEMISTRY
UR  - http://pubs.rsc.org/en/Content/ArticleLanding/2016/CC/C6CC07496K#!divAbstract
L2  - http://pubs.rsc.org/en/Content/ArticleLanding/2016/CC/C6CC07496K#!divAbstract
N2  - A bioorthogonal 'catch and photorelease' strategy, which combines alkyne-azide cycloaddition between p-hydroxyphenacyl azide and alkyne derivatives to form a 1,2,3-triazole adduct and subsequent photochemical release of the triazole moiety via a photo-Favorskii rearrangement, is introduced. The first step can also involve photo-release of a strained alkyne and its Cu-free click reaction with azide.
ER  -

MADEA, Dominik, Tomáš SLANINA and Petr KLÁN. A 'photorelease, catch and photorelease' strategy for bioconjugation utilizing a p-hydroxyphenacyl group. \textit{Chemical communications}. Cambridge: Royal Society of Chemistry, 2016, vol.~52, No~87, p.~12901-12904. ISSN~1359-7345. Available from: https://dx.doi.org/10.1039/c6cc07496k.

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