An enzymatic acetal/hemiacetal conversion for the physiological temperature activation of the alkoxyamine C–ON bond homolysis
Literature Information
Publication Date
2020-07-30
DOI
10.1039/D0QO00559B
Impact Factor
5.281
Authors
Muriel Albalat, Gérard Audran, Maxence Holzritter, Sylvain R. A. Marque, Nicolas Vanthuyne, Pierre Voisin
View Original
Abstract
The potential of alkoxyamines as theranostic agents has been recently promoted by our groups. The success of such an approach relies on the switch upon enzymatic triggering between highly stable precursor alkoxyamines and activated alkoxyamines exhibiting fast homolysis of the C–ON bond. Hence, at 37 °C in water, benzyl 2-(2,2,6,6-tetramethylpiperidin-N-oxy)-3-ethoxy-3-acetoxypropanoate and benzyl 2-ditert-butylaminoxy-3-ethoxy-3-acetoxy propanoate afford tmax of 2000 s (35% conversion) and 500 s (60% conversion), respectively, for the C–ON bond homolysis in the presence of Subtilisin A whereas t1/2 of ca. 42 thousand millenniums and 330 years are expected accordingly to Ea values in n-propanol. These results nicely highlight the on/off switch, provided that an enzymatic activity controls the C–ON bond homolysis.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
(1-(2-(Dimethylamino)ethyl)-1H-pyrazol-4-yl)boronic acid
CAS Number:
1086063-73-1
Molecular Formula:
C7H14BN3O2
1-(5-Bromo-2-fluorophenyl)-2,2,2-trifluoroethanol
CAS Number:
1039827-16-1
Molecular Formula:
C8H5BrF4O
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