n-benzyloxycarbonylglycine 4-nitrophenyl ester

Description

n-Benzyloxycarbonylglycine 4-nitrophenyl ester, also known as Z-Gly-ONp, is a valuable reagent in peptide synthesis. It is an activated ester of N-benzyloxycarbonylglycine (Z-Gly), a common protecting group for amino acids. The 4-nitrophenyl group serves as a good leaving group, facilitating the formation of peptide bonds. This compound is commonly employed in solid-phase peptide synthesis (SPPS), a method for constructing peptides on a solid support. Its use in SPPS allows for the efficient and controlled synthesis of peptides with specific sequences. The 4-nitrophenyl ester enhances the reactivity of the carboxyl group, facilitating coupling reactions with amino acids attached to the solid support. Z-Gly-ONp is known to be a stable compound under typical peptide synthesis conditions. It is typically synthesized by reacting N-benzyloxycarbonylglycine with 4-nitrophenol in the presence of a coupling reagent, such as dicyclohexylcarbodiimide (DCC). The synthesis of peptides using Z-Gly-ONp involves the activation of the carboxyl group of Z-Gly-ONp, followed by the coupling reaction with the amino group of the next amino acid. This process is repeated to form the desired peptide sequence. The study of n-Benzyloxycarbonylglycine 4-nitrophenyl ester is important due to its role in peptide synthesis, a fundamental technique in biochemistry, pharmaceuticals, and materials science. Understanding its properties, reactivity, and application in SPPS is crucial for the development of new peptides with therapeutic, diagnostic, and industrial applications.'
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N-benzyloxycarbonylglycine 4-nitrophenyl ester: hydrolyzed by papain [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]