Photorelease of Carboxylic Acids, Amino Acids, and Phosphates from N-Alkylpicolinium Esters Using Photosensitization by High Wavelength Laser Dyes
- 12 May 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (22) , 8000-8001
- https://doi.org/10.1021/ja050760f
Abstract
Visible light (>450 nm) is used to efficiently cleave carboxylic acids, amino acids, and phosphates from their N-methyl picolinium esters. Photolysis using pyrromethene dyes PM 546 and PM 597 and also coumarin 6 as photosensitizers effects release of carboxylic acids, N-protected amino acids, and phosphates in quantitative yields. The effective rate of photorelease by the dyes, Φε, was found to be as high as 4500 M-1 cm-1. The photorelease proceeds through photoinduced electron transfer from the dye sensitizers to the N-methyl picolinium group. Fluorescence quenching and laser flash photolysis experiments support the photoinduced electron-transfer mechanism.Keywords
This publication has 14 references indexed in Scilit:
- 2,5-Dimethylphenacyl carbonates: A photoremovable protecting group for alcohols and phenolsPublished by Springer Nature ,2004
- C−O Bond Fragmentation of 4-Picolyl- and N-Methyl-4-picolinium Esters Triggered by Photochemical Electron TransferThe Journal of Organic Chemistry, 2004
- Photochemical Reaction Mechanisms of 2-Nitrobenzyl Compounds: Methyl Ethers and Caged ATPJournal of the American Chemical Society, 2004
- Triplet-Sensitized Photodeprotection of Oligonucleotides in Solution and on Microarray ChipsHelvetica Chimica Acta, 2004
- Mechanism of Pyrrolyl Oxidation in Star-Shaped CompoundsThe Journal of Physical Chemistry A, 2003
- Photoenolization as a Means To Release AlcoholsThe Journal of Organic Chemistry, 2003
- Wavelength-Controlled Orthogonal Photolysis of Protecting GroupsThe Journal of Organic Chemistry, 2002
- New Phototriggers 9: p-Hydroxyphenacyl as a C-Terminal Photoremovable Protecting Group for OligopeptidesJournal of the American Chemical Society, 2000
- Protecting Groups That Can Be Removed through Photochemical Electron Transfer: Mechanistic and Product Studies on Photosensitized Release of Carboxylates from Phenacyl EstersThe Journal of Organic Chemistry, 1997
- Rauwolfia alkaloid synthesis approach employing the zwitterionic amino-Claisen rearrangement. Improvements in the efficiency for yohimbane ring construction and unambiguous de-ring-fusion stereochemical assignmentsThe Journal of Organic Chemistry, 1984