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@article{699363,
author = {Kammari, Laxminarayana and Plíštil, Lukáš and Wirz, Jakob and Klán, Petr},
article_location = {Cambridge, United Kingdom},
article_number = {1},
keywords = {Photochemistry; photoremovable protecting groups; amines; amino acids},
language = {eng},
issn = {1474-905X},
journal = {Photochemical and Photobiological Sciences},
title = {2,5-Dimethylphenacyl carbamate: A photoremovable protecting group for amines and amino acids},
volume = {6},
year = {2007}
}
TY - JOUR
ID - 699363
AU - Kammari, Laxminarayana - Plíštil, Lukáš - Wirz, Jakob - Klán, Petr
PY - 2007
TI - 2,5-Dimethylphenacyl carbamate: A photoremovable protecting group for amines and amino acids
JF - Photochemical and Photobiological Sciences
VL - 6
IS - 1
SP - 50-56
EP - 50-56
PB - Royal Society of Chemistry
SN - 1474905X
KW - Photochemistry
KW - photoremovable protecting groups
KW - amines
KW - amino acids
N2 - 2,5-Dimethylphenacyl (DMP) carbamates (1a-c) released the corresponding free amines or amino acid in high chemical yields, albeit with quantum yields of only 0.04-0.09, upon irradiation in either aprotic or protic solvents. The photoreaction proceeded principally from the triplet excited state via the E-photoenol. The lifetimes of the triplet enol and of the E- and Z-enols in the ground state were determined by laser flash photolysis. The primary photoinitiated transformation liberated a carbamic acid derivative, which subsequently decarboxylated to the amino group containing compound. Exhaustive irradiation of a DMP-protected aniline (1a) in acetonitrile did not provide aniline in quantitative chemical yields, because it was involved in reductive cleavage of the starting material as an electron donor, thereby decreasing the overall deprotection yield (86%). Phenylalanine methyl ester, liberated from 1c, was, however, obtained in excellent chemical yields (97%). It was also found that the carbamates, while thermally stable, released amines with higher quantum yields in acidic methanol solutions. The DMP chromophore is proposed as an excellent photoremovable protecting group for amino acids and, under specific conditions, also for amines in organic synthesis and biochemistry.
ER -
KAMMARI, Laxminarayana, Lukáš PLÍŠTIL, Jakob WIRZ and Petr KLÁN. 2,5-Dimethylphenacyl carbamate: A photoremovable protecting group for amines and amino acids. \textit{Photochemical and Photobiological Sciences}. Cambridge, United Kingdom: Royal Society of Chemistry, 2007, vol.~6, No~1, p.~50-56. ISSN~1474-905X.
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