Brominated hydroxyquinoline as a photolabile protecting group with sensitivity to multiphoton excitation

Olesya D. Fedoryak; Timothy M. Dore

doi:10.1021/ol026524g

Brominated hydroxyquinoline as a photolabile protecting group with sensitivity to multiphoton excitation

Olesya D. Fedoryak, Timothy M. Dore

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

(matrix presented) The synthesis and photochemistry of a new photolabile protecting group for carboxylic acids based on 8-bromo-7-hydroxyquinoline (BHQ) is described. BHQ possesses a greater single photon quantum efficiency than 4,5-dimethoxy-4-nitrobenzyl ester (DMNB) and 6-bromo-7-hydroxycoumarin-4-ylmethyl (Bhc), and it has sufficient sensitivity to multiphoton-induced photolysis for use in vivo. Its increased solubility and low fluorescence make it quite useful as a caging group for biological messengers.

Original language	English (US)
Pages (from-to)	3419-3422
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	20
DOIs	https://doi.org/10.1021/ol026524g
State	Published - Oct 3 2002

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol026524g

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abstract = "(matrix presented) The synthesis and photochemistry of a new photolabile protecting group for carboxylic acids based on 8-bromo-7-hydroxyquinoline (BHQ) is described. BHQ possesses a greater single photon quantum efficiency than 4,5-dimethoxy-4-nitrobenzyl ester (DMNB) and 6-bromo-7-hydroxycoumarin-4-ylmethyl (Bhc), and it has sufficient sensitivity to multiphoton-induced photolysis for use in vivo. Its increased solubility and low fluorescence make it quite useful as a caging group for biological messengers.",

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year = "2002",

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doi = "10.1021/ol026524g",

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AU - Fedoryak, Olesya D.

AU - Dore, Timothy M.

PY - 2002/10/3

Y1 - 2002/10/3

N2 - (matrix presented) The synthesis and photochemistry of a new photolabile protecting group for carboxylic acids based on 8-bromo-7-hydroxyquinoline (BHQ) is described. BHQ possesses a greater single photon quantum efficiency than 4,5-dimethoxy-4-nitrobenzyl ester (DMNB) and 6-bromo-7-hydroxycoumarin-4-ylmethyl (Bhc), and it has sufficient sensitivity to multiphoton-induced photolysis for use in vivo. Its increased solubility and low fluorescence make it quite useful as a caging group for biological messengers.

AB - (matrix presented) The synthesis and photochemistry of a new photolabile protecting group for carboxylic acids based on 8-bromo-7-hydroxyquinoline (BHQ) is described. BHQ possesses a greater single photon quantum efficiency than 4,5-dimethoxy-4-nitrobenzyl ester (DMNB) and 6-bromo-7-hydroxycoumarin-4-ylmethyl (Bhc), and it has sufficient sensitivity to multiphoton-induced photolysis for use in vivo. Its increased solubility and low fluorescence make it quite useful as a caging group for biological messengers.

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Brominated hydroxyquinoline as a photolabile protecting group with sensitivity to multiphoton excitation

Abstract

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