Carbanion-Mediated Photocages:  Rapid and Efficient Photorelease with Aqueous Compatibility

Lukeman, Matthew; Scaiano, Juan C.

doi:10.1021/ja0517062

Cited by 71 publications

(84 citation statements)

References 11 publications

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“…The key property of a suitable protecting group is rapid and efficient deprotection reaction upon photoirradiation. For this purpose, we employed a ketoprofen-type photolabile protecting group, 40) and developed SPD-1 and -2 10,11) (Fig. 1, 7, 8).…”

Section: Photocontrollable H 2 S Releasersmentioning

confidence: 99%

Photocontrol of NO, H<sub>2</sub>S, and HNO Release in Biological Systems by Using Specific Caged Compounds

Nakagawa

2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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Nitric oxide (NO) is a gas that plays various roles in physiological signal transduction, for example, in vasodilation, neural transmission, and biodefence. Recently, other gaseous signal mediators such as carbon monoxide (CO) and hydrogen sulfide (H 2 S) have also been found to have important biological activities. Since experimental studies with gaseous mediators are difficult, chemicals that enable controlled release of these gases are indispensable. We have developed a range of photocontrollable releasers that generate NO, H 2 S, and related species with fine spatiotemporal control, and we have also employed these caged compounds in various applications. This paper briefly reviews our work on photocontrollable NO, H 2 S, and HNO releasers, and presents some typical applications illustrating the suitability of our compounds for controlled release of these biologically active species in cellular and tissue systems. These compounds also appear to have potential for future therapeutic applications.

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Section: Photocontrollable H 2 S Releasersmentioning

confidence: 99%

Photocontrol of NO, H<sub>2</sub>S, and HNO Release in Biological Systems by Using Specific Caged Compounds

Nakagawa

2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Synthesis of (RS)-Ketoprofen Methyl Ester (9) [27] To a 250-mL round bottom flask was added (RS)-ketroprofen (12.74 g, 0.05 mol), methanol (100 mL) and H 2 SO 4 (1 mL). The flask was fitted with a reflux condenser and the mixture was refluxed.…”

Section: General Procedures For Chemical Synthesis Of Racemic Menthyl mentioning

confidence: 99%

Enzymatic Production of l‐Menthol by a High Substrate Concentration Tolerable Esterase from Newly Isolated Bacillus subtilis ECU0554

Zheng

Zhang

et al. 2009

Adv Synth Catal

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Enzymatic preparation of l-menthol has been attracting much attention in the flavor and fragrance industry. A new ideal strain, Bacillus subtilis ECU0554, which exhibited high hydrolytic activity and excellent enantioselectivity towards l-menthyl ester, has been successfully isolated from soil samples through enrichment culture and identified as Bacillus subtilis by 16S rDNA gene sequencing. The esterase extracted from B. subtilis ECU0554 (BSE) showed the best catalytic properties (E > 200) for dlmenthyl acetate among the five menthyl esters examined. Enantioselective hydrolysis of 100 mM dlmenthyl acetate at 308C and pH 7.0, using crude BSE as biocatalyst and 10% ethanol (v/v) as cosolvent, resulted in 49.0% conversion (3 h) and 98.0% ee for the l-menthol produced, which were much better than those using commercial enzymes tested.Moreover, BSE exhibited strong tolerance against high substrate concentration (up to 500 mM), and the concentration of l-menthol produced could reach as high as 182 mM, and more importantly, the optical purity of l-menthol produced was kept above 97% ee, which were not found in previous reports. These results imply that BSE is a potentially promising biocatalyst for the large-scale enzymatic preparation of l-menthol. Using this excellent biocatalyst, the enzymatic production of l-menthol will become a mild, efficient, inexpensive and easy-to-use "green chemistry" methodology.

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“…Photochemically induced decarboxylation reactions have been extensively investigated [1][2][3] because of their importance in organic synthesis, [4,5] the development of photocages, [6,7] and materials science [8] as well as the fact that some nonsteroidal anti-inflamatory drugs can induce a photoallergic response as a result of undergoing a photodecarboxylation process. [9][10][11][12] Photocatalytic decarboxylation reactions have recently experienced a revival in organic synthesis, [13][14][15][16][17][18] and significant progress has been made to elucidate the photodecarboxylation reaction mechanism that leads to anionic species.…”

Section: Introductionmentioning

confidence: 99%

Photodecarboxylation of Adamantane Amino Acids Activated by Phthalimide

et al. 2016

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Adamantane α‐, β‐, and δ‐amino acids activated by phthalimide (i.e., 3–6) were synthesized, and their photochemical reactivities were investigated. Amino acid derivatives 3–6 underwent a photoinduced electron transfer (PET) and decarboxylation reaction sequence, most probably through a triplet excited state. The decarboxylations of the β‐amino acid derivatives were succeeded by cyclization reactions that afforded complex polycyclic molecules with potential biological interest. The adamantyl radical that is produced by the photoinduced decarboxylation could be trapped by alkenes or oxygen to deliver adducts or alcohols, respectively. The photodecarboxylation process was shown to be more efficient under acetone sensitization conditions (with quantum yields, Φ = 0.02–0.5) than upon direct excitation, and the reactivity was dependent on the chain length (intramolecular distance) between the electron donor (carboxylate) and acceptor (phthalimide in the triplet excited state) of the derivative. The formation of different radicals, that is, the 1‐ or 2‐adamantyl intermediate, probably does not affect the overall rate of the decarboxylation This current report provides a better understanding of photodecarboxylation and the rational design of molecular systems to undergo photoinduced decarboxylation and cyclization reactions.

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Carbanion-Mediated Photocages: Rapid and Efficient Photorelease with Aqueous Compatibility

Cited by 71 publications

References 11 publications

Photocontrol of NO, H<sub>2</sub>S, and HNO Release in Biological Systems by Using Specific Caged Compounds

Photocontrol of NO, H<sub>2</sub>S, and HNO Release in Biological Systems by Using Specific Caged Compounds

Enzymatic Production of l‐Menthol by a High Substrate Concentration Tolerable Esterase from Newly Isolated Bacillus subtilis ECU0554

Photodecarboxylation of Adamantane Amino Acids Activated by Phthalimide

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