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Literature DB >> 14653694

Coumarin-4-ylmethoxycarbonyls as phototriggers for alcohols and phenols.

Akinobu Z Suzuki¹, Takayoshi Watanabe, Mika Kawamoto, Keiko Nishiyama, Hirotaka Yamashita, Megumi Ishii, Michiko Iwamura, Toshiaki Furuta.

Abstract

Caged compounds can be used to regulate the spatial and temporal dynamics of signaling molecules in live cells. Photochemical properties of coumarin-4-ylmethoxy carbonates (1a-d) are investigated to construct caged compounds of hydroxy-containing molecules. All the compounds possess desired properties as phototriggers for alcohols and phenols. The 6-bromo-7-hydroxycoumarin-4-ylmethoxycarbonyl (Bhcmoc) group has the highest photochemical efficiency and is applied to make caged compounds of 1,2-dioctanoylglycerol (diC(8)), Tyr-OMe, and adenosine. [reaction: see text]

Entities: Chemical

Year: 2003 PMID： 14653694 DOI： 10.1021/ol0359362

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

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Cited

24 in total

Review 1. Photochemical approaches to T-cell activation.

Authors: Morgan Huse
Journal: Immunology Date: 2010-04-06 Impact factor: 7.397

2. 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

Coumarin-4-ylmethoxycarbonyls as phototriggers for alcohols and phenols.

Review 1. Photochemical approaches to T-cell activation.

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

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

Review 4. From lipid second messengers to molecular motors: microtubule-organizing center reorientation in T cells.

5. Spacer-Mediated Control of Coumarin Uncaging for Photocaged Thymidine.

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

Review 7. Applications of p-hydroxyphenacyl (pHP) and coumarin-4-ylmethyl photoremovable protecting groups.

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

9. A Single UV or Near IR Triggering Event Leads to Polymer Degradation into Small Molecules.

10. Localized diacylglycerol drives the polarization of the microtubule-organizing center in T cells.