New Phototriggers:1 Extending the p-Hydroxyphenacyl π−π Absorption Range

Introducing 3-methoxy or 3,5-dimethoxy substituents on the 4-hydroxyphenacyl (pHP) photoremovable protecting group has been explored with two excitatory γ-amino acids, l-glutamic acid and γ-amino butyric acid (GABA). These substituents significantly extend the absorption range of the pHP chromophore...

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Veröffentlicht in:Organic letters 2000-06, Vol.2 (11), p.1545-1547
Hauptverfasser: Conrad, Peter G, Givens, Richard S, Weber, Jörg F. W, Kandler, Karl
Format: Artikel
Sprache:eng
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Zusammenfassung:Introducing 3-methoxy or 3,5-dimethoxy substituents on the 4-hydroxyphenacyl (pHP) photoremovable protecting group has been explored with two excitatory γ-amino acids, l-glutamic acid and γ-amino butyric acid (GABA). These substituents significantly extend the absorption range of the pHP chromophore, e.g., the tail of absorption bands of 2a,b extend above 400 nm, well beyond the absorptions of aromatic amino acids and nucleotides. Irradiation releases the amino acids with rate constants of ∼107 s-1 and appearance efficiencies (Φapp) of 0.03−0.04. The photoproducts are formed through the pHP excited triplet and are primarily products of photoreduction and photohydrolysis. 1a,b also rearranged to the phenylacetic acid 3.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol005856n