92989-59-8Relevant academic research and scientific papers
Modulated photochemical reactivities of: O -acetylated (3′,5′-dimethoxyphenyl)heteroaryl acyloin derivatives under direct irradiation and photo-induced electron transfer conditions
Bisht, Rajesh,Singh, Saumya,Krishnamoorthy, Kothandam,Nithyanandhan, Jayaraj
, p. 835 - 845 (2018/06/21)
3′,5′-Dimethoxybenzoin esters are important photoremovable protecting groups which form 2-phenylbenzofuran derivatives upon photo-release. We utilized a similar concept to test a photochemical method of installing a benzofuran moiety to the conjugated bac
Wavelength-orthogonal photolysis of neurotransmitters in vitro
Stanton-Humphreys, Megan N.,Taylor, Ruth D. T.,McDougall, Craig,Hart, Mike L.,Brown, C. Tom A.,Emptage, Nigel J.,Conway, Stuart J.
supporting information; scheme or table, p. 657 - 659 (2012/02/02)
Irradiation of a mixture of 4-methoxyphenacyl-caged (S)-glutamate and 4,5-dimethoxy-2-nitrobenzyl-caged γ-amino butyric acid (GABA) on neurons, at ～260 nm, evokes selective photorelease of (S)-glutamate (Glu) whereas photolysis at 405 nm causes selective photorelease of GABA.
A time-resolved spectroscopic study of the bichromophoric phototrigger 3',5'-dimethoxybenzoin diethyl phosphate: Interaction between the two chromophores determines the reaction pathway
Chensheng, Ma.,Kwok, Wai Ming,An, Hui-Ying,Guan, Xiangguo,Fu, Michael Yunyi,Toy, Patrick H.,Phillips, David Lee
supporting information; experimental part, p. 5102 - 5118 (2010/08/05)
3',5'-Dimethoxybenzoin (DMB) is a bichromophoric system that has widespread application as a highly efficient photoremovable protecting group (PRPG) for the release of diverse functional groups. The photodeprotection of DMB phototriggers is remarkably cle
Wavelength-controlled orthogonal photolysis of protecting groups
Blanc, Aurelien,Bochet, Christian G.
, p. 5567 - 5577 (2007/10/03)
The selective control of a chemical process by the use of an electromagnetic wave has been a challenging goal for several decades. In this article, we describe for the first time the use of a monochromatic light beam to differentiate two different reactive centers. A direct application of this concept is found in the chemistry of protecting groups. Two different photolabile protecting groups were tuned to be responsive to a specific wavelength (e.g., 254 or 420 nm). Using derivatives of the 2-nitroveratryl fragment (such as 10, sensitive at 420 nm) and 3′,5′-dimethoxybenzoin fragment (such as 4, sensitive at 254 nm), it was shown that energy transfer phenomena did not erode the selectivity. Both the inter- and the intramolecular cases were studied and showed selectivities within the synthetically useful range. Hence, we could replace the traditional chemical orthogonality by a chromatic orthogonality.
Design, synthesis, and photochemical properties of a photoreleasable ubiquinol-2: A novel compound for studying rapid electron-transfer kinetics in ubiquinol-oxidizing enzymes
Wang, Guangyang
, p. 1657 - 1664 (2007/10/03)
The design and multistep convergent synthesis of the novel photoactive ubiquinol-benzoin adduct 1a,b has been accomplished. Optical spectra of the steady-state photolysis reactions showed a smooth conversion from 1a,b to 5,7-dimethoxy-2-phenylbenzofuran (13) and ubiquinol-2 with an isobestic point at 258 nm. HPLC analysis of the photoproducts was also consistent with the clean formation of the desired ubiquinol-2 (3) and the expected 5,7-dimethoxy-2-phenylbenzofuran (2). Transient photolysis at 355 nm was consistent with a rapid photolysis rate that exceeded the instrument response time (> 106 s-1). Accordingly, the study of rapid electron-transfer events in ubiquinol oxidizing enzymes is now feasible. Furthermore, the synthetic methods developed herein will be of general application for the facile synthesis of a variety of photoreleasable substrates for studying rapid kinetic events in enzymatic reactions.
Efficient synthesis of photolabile alkoxy benzoin protecting groups
Stowell, Michael H.B.,Rock, Ronald S.,Rees,Chan, Sunney I.
, p. 307 - 310 (2007/10/02)
An effective implementation of the Corey-Seebach dithiane addition for the synthesis of photolabile alkoxy benzoin adducts is reported. The method allows for the facile synthesis of photolabile 3',5'-dimethoxybenzoin protected compounds in near quantitati
