Sulfamoylation of the L-ornithine methyl esterside-chain generates a non-natural arginine isostere whichcan be coupled with N-Fmoc-L-proline to synthesize analogueswhich maintain the structural characteristics of thebiologically important Pro-Arg dipeptide sequence. As aprobe of its biological importance, the sulfamoylatedamino acid derivative was also incorporated as P1 residuein tripeptide structures matching the C-terminal subsequenceof fibrinogen. The reported results demonstrate thatthe functionalization of L-ornithine side-chain with a neutralsulfamoyl group can generate an arginine bioisosterewhich can be used for the synthesis of prototypes of a newclass of human thrombin inhibitors.

A new non-natural arginine-like amino acid derivative with a sulfamoyl group in the side-chain

DI GIOIA, Maria Luisa;LEGGIO, Antonella;LIGUORI, Angelo;SICILIANO, Carlo;
2010-01-01

Abstract

Sulfamoylation of the L-ornithine methyl esterside-chain generates a non-natural arginine isostere whichcan be coupled with N-Fmoc-L-proline to synthesize analogueswhich maintain the structural characteristics of thebiologically important Pro-Arg dipeptide sequence. As aprobe of its biological importance, the sulfamoylatedamino acid derivative was also incorporated as P1 residuein tripeptide structures matching the C-terminal subsequenceof fibrinogen. The reported results demonstrate thatthe functionalization of L-ornithine side-chain with a neutralsulfamoyl group can generate an arginine bioisosterewhich can be used for the synthesis of prototypes of a newclass of human thrombin inhibitors.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11770/124290
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