2-Hydroxyphenacyl ester: a new photoremovable protecting group

被引：18

作者：

Ngoy, Bokolombe Pitchou ^{[1
,2
]}

Sebej, Peter ^{[1
,2
]}

Solomek, Tomas ^{[1
,2
]}

Lim, Bum Hee ^{[3
]}

Pastierik, Tomas ^{[1
]}

Park, Bong Ser ^{[3
]}

Givens, Richard S. ^{[4
]}

Heger, Dominik ^{[1
,2
]}

Klan, Petr ^{[1
,2
]}

机构：

[1] Masaryk Univ, Fac Sci, Dept Chem, Brno 62500, Czech Republic

[2] Masaryk Univ, Fac Sci, Res Ctr Tox Cpds Environm, Brno 62500, Czech Republic

[3] Dongguk Univ, Dept Chem, Seoul 100715, South Korea

[4] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA

来源：

PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES | 2012年 / 11卷 / 09期

关键词：

INTRAMOLECULAR PROTON-TRANSFER; P-HYDROXYPHENACYL; EXCITED-STATE; RESONANCE RAMAN; TRIPLET-STATE; PHOTOCYCLIZATION; HYDROXYACETOPHENONE; HYDROXYBENZALDEHYDE; PHOTOCHEMISTRY; PHOTOTRIGGERS;

D O I：

10.1039/c2pp25133g

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：1465 / 1475

页数：11

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