Ac-Gly-ONp is an N-acetylated glycine amide derivative in which the carboxyl group is converted to an ONp ester (p-nitrophenyl ester), yielding a protected, activated amino acid building block rather than a free amino acid. The molecule contains an N-acetyl (Ac) protecting group on the amino nitrogen and a glycine backbone with a primary amide-forming functionality, while the p-nitrophenyl ester provides a leaving group-bearing carbonyl for controlled acyl transfer chemistry. Ac-Gly-ONp is used in peptide chemistry and related synthesis as an activated glycine acylating reagent or intermediate to access glycine-containing amide linkages under conditions where chemoselective coupling to nucleophiles is required.
CAT No: CP25757
CAS No:3304-61-8
Synonyms/Alias:p-NitrophenylN-acetylglycinate;AC-GLY-ONP;3304-61-8;4-nitrophenyl2-acetamidoacetate;AmbotzAAA1916;AC1NO0PM;SCHEMBL9491502;CHEMBL3278893;CTK8B8580;MolPort-002-474-574;(4-nitrophenyl)2-acetamidoacetate;ZINC2581985;ANW-60741;AKOS016003518;AK-81087;AM022411;OR024222;KB-259338;TC-149486;K-7633;3B3-059657
Chemical Name:N-alpha-Acetyl-glycine p-nitrophenyl ester
Ac-Gly-ONp is an N-acetylated glycine ONp ester (ONp = p-nitrophenyl), providing an activated carboxylate format commonly used to generate amide bonds under mild conditions. This structure combines a protected amino terminus (acetylated) with a leaving-group-bearing ester, making it a practical electrophilic building block for peptide-related coupling and for preparing glycine-containing intermediates in solution-phase workflows where controlled reactivity is beneficial.
1. Solution-Phase Amide Coupling
Ac-Gly-ONp is used by peptide and medicinal chemistry groups as an activated glycine ester for forming amide linkages with amine-containing partners. The p-nitrophenyl leaving group supports efficient coupling in standard organic synthesis and custom peptide intermediate development, allowing researchers to assemble glycine-containing motifs without requiring pre-activation of the carboxylic acid. Because the amino group is acetyl-protected, the reagent directs reactivity primarily toward the activated ester, which helps streamline downstream purification and minimizes competing amino-site reactions.
2. Peptide Fragment Synthesis
Ac-Gly-ONp serves as a practical electrophile for constructing short peptide fragments where glycine must be introduced as a defined, acetylated unit. In custom peptide synthesis workflows, the reagent can be used to couple glycine into larger sequences or to prepare protected glycine termini for subsequent transformations. The ONp ester format is especially useful in solution-phase fragment assembly, supporting stepwise build strategies used by contract synthesis teams and research laboratories developing peptide libraries and peptidomimetic scaffolds.
3. Activated Glycine Intermediate
Ac-Gly-ONp is frequently selected as a high-reactivity intermediate for preparing amide-containing intermediates in pharmaceutical intermediate programs. Process and R&D chemists use this reagent to rapidly convert amine nucleophiles into glycine-derived amides while maintaining the acetylated amino functionality as a stable protecting pattern during the coupling step. This makes Ac-Gly-ONp a convenient choice when the goal is controlled incorporation of glycine into a target intermediate, followed by further functional group elaboration in the same synthetic campaign.
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