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Literature DB >> 12790543

Bhc-diol as a photolabile protecting group for aldehydes and ketones.

Min Lu¹, Olesya D Fedoryak, Brent R Moister, Timothy M Dore.

Abstract

[reaction: see text] 6-Bromo-4-(1,2-dihydroxyethyl)-7-hydroxycoumarin (Bhc-diol) can be used under simulated physiological conditions as a photoremovable protecting group for aldehydes and ketones. The single- and two-photon-induced release of benzaldehyde, piperonal, acetophenone, and cyclohexanone is demonstrated.

Entities: Chemical

Year: 2003 PMID： 12790543 DOI： 10.1021/ol034536b

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

11 in total

1. Improved synthesis of the two-photon caging group 3-nitro-2-ethyldibenzofuran and its application to a caged thymidine phosphoramidite.

Authors: Hrvoje Lusic; Rajendra Uprety; Alexander Deiters
Journal: Org Lett Date: 2010-03-05 Impact factor: 6.005

2. Alcohol, Aldehyde, and Ketone Liberation and Intracellular Cargo Release through Peroxide-Mediated α-Boryl Ether Fragmentation.

Authors: Ramsey D Hanna; Yuta Naro; Alexander Deiters; Paul E Floreancig
Journal: J Am Chem Soc Date: 2016-09-30 Impact factor: 15.419

Bhc-diol as a photolabile protecting group for aldehydes and ketones.

1. Improved synthesis of the two-photon caging group 3-nitro-2-ethyldibenzofuran and its application to a caged thymidine phosphoramidite.

2. Alcohol, Aldehyde, and Ketone Liberation and Intracellular Cargo Release through Peroxide-Mediated α-Boryl Ether Fragmentation.

Review 3. Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy.

4. Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials.

5. Light-activated serotonin for exploring its action in biological systems.

Review 6. Applications of p-hydroxyphenacyl (pHP) and coumarin-4-ylmethyl photoremovable protecting groups.

7. Novel photoactivatable substrates for Renilla luciferase imaging in vitro and in vivo.

8. Two-photon photochemical generation of reactive enediyne.

9. Synthetic caged DAG-lactones for photochemically controlled activation of protein kinase C.

10. Quinoline-Derived Two-Photon-Sensitive Octupolar Probes.