Chemical Carbonylation of Arginine in Peptides and Proteins
AssigneeEmory University
InventorMonika Raj
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Abstract
Disclosed herein are methods of oxidizing a guanidine group comprising contacting a compound or peptide having a guanidine group with a 9,10-phenanthrenequinone or derivative providing compound with an aldehyde group in place of the guanidine group. In certain embodiments, the guanidine group is an arginine amino acid within a protein. In certain embodiments, this disclosure relates to compositions comprising 9,10-phenanthrenequinone derivatives as provided herein.
Claims20
A method of oxidizing a guanidine group comprising contacting a compound having a guanidine group with a 9,10-phenanthrenequinone or derivative and a base providing compound with an aldehyde group in place of the guanidine group.
A composition comprising a 9,10-phenanthrenequinone derivative having the following formula I,
- or salt thereof, wherein
- X is N or CR4;
- Y is N or CR5;
- R1, R2, R3, R4, R5, R6, R7 and R8 are individually selected from hydrogen, C1-10 alkyl, C2-10 alkenyl or C2-10 alkynyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, hydroxyalkyl, glycol, alkylthio, thioalkyl, alkylamino, aminoalkyl, (alkyl)2amino, alkanoyl, alkoxycarbonyl, carbocyclyl, benzoyl, benzyl, aryl, or heterocyclyl, wherein each R1, R2, R3, R4, R5, R6, R7 and R8 are optionally substituted with one or more, the same or different, R9;
- and
- R9 is C1-10 alkyl, C2-10 alkenyl or C2-10 alkynyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, hydroxyalkyl, glycol, alkylthio, thioalkyl, alkylamino, aminoalkyl, (alkyl)2amino, alkanoyl, alkoxycarbonyl, carbocyclyl, benzoyl, benzyl, aryl, or heterocyclyl, wherein R9 is optionally substituted with one or more, the same or different, R10;
- or
- R10 is halogen, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, amino, formyl, carboxy, carbamoyl, mercapto, sulfamoyl, methyl, ethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, hydroxymethyl, hydroxyethyl, thiomethyl, thioethyl, aminomethyl, aminoethyl, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino, N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, tert-butoxycarbonyl, benzoyl, benzyl, carbocyclyl, aryl, or heterocyclyl.
Dependencies are inferred from the claim text.