Ac-Gly-NHMe is an N-acetylated glycinamide derivative in which the glycine backbone bears an acetamide-protected amino terminus (Ac-) and a N-methylamide at the carboxamide end (-NHMe), classifying it as a peptide-like amino acid amide rather than a free amino acid. The molecule contains an amide-linked carbonyl from the acetyl group and a second amide carbonyl within the glycinamide, with the side chain reduced to a hydrogen substituent characteristic of glycine, and it lacks a free carboxylic acid and free amino group due to amide formation. Ac-Gly-NHMe is used as a defined peptide fragment or substrate analogue in peptide chemistry and chemical biology workflows, including structure-reactivity studies, analytical method development for amide-containing glycyl motifs, and the preparation of further peptide derivatives through controlled amide chemistry.
CAT No: CP27436
CAS No:7606-79-3
Synonyms/Alias:2-acetamido-N-methylacetamide;7606-79-3;CaseinK;Ac-Gly-NHMe;Acetyl-glycinemethylamide;AC1L97HE;N-AcetylglycineN-methylamide;SCHEMBL3623995;CHEBI:74101;N(2)-acetyl-N-methylglycinamide;MolPort-003-917-775;ZINC399466;2-(Acetylamino)-N-methylethanamide;4960AH;KM1735;AKOS006242075;MCULE-3508245247;RP19914;KB-114138
Ac-Gly-NHMe is an N-acetylated glycinamide (N-acetylglycinamide) featuring a glycine backbone capped as an acetamide on the N-terminus and a methylamide at the C-terminus, yielding a neutral, peptide-like, amide-rich small molecule. This structure is frequently used as a minimal model substrate and building block in peptide chemistry workflows where an uncharged glycinamide motif is required for controlled reactivity and reproducible analytical behavior.
1. Peptide Bond Modeling
Ac-Gly-NHMe is used as a compact glycinamide model compound for evaluating peptide coupling conditions, amide reactivity trends, and downstream derivatization compatibility in peptide chemistry development. Researchers often select this motif because it mimics key local functional-group patterns of short peptides while remaining small enough for rapid screening and method optimization. The N-acetyl and C-methylamide capping also help reduce variability associated with free termini, supporting more consistent comparisons across analogs in custom peptide synthesis research.
2. Amide Reactivity Standards
Ac-Gly-NHMe serves as a practical reference substrate for analytical and synthetic studies focused on amide formation, acyl transfer, and acylation efficiency in the context of peptide intermediate development. Its defined, peptide-like amide functionality makes it useful for method qualification in LC-based assays where consistent chromatographic and ionization behavior is needed. In process development settings, it can be used to benchmark derivatization or coupling steps that target glycinamide-containing fragments, supporting reproducible workflow tuning for larger peptide assemblies.
3. Chemical Biology Substrate Probes
Ac-Gly-NHMe is applied in chemical biology experiments that require a simplified glycinamide-containing substrate to probe amide-processing chemistry or enzyme-adjacent reactivity in vitro, without introducing charged termini. Because it presents a stable, defined di-amide pattern, it is commonly used when researchers need a small, controllable substrate analogue that can be monitored by analytical readouts such as LC-MS. This makes it useful for studying substrate scope, reaction compatibility, and assay robustness in workflows that involve short peptide-like fragments rather than full-length peptides.
4. Pharmaceutical Intermediate Building Block
Ac-Gly-NHMe is also used as a specialty intermediate building block for preparing glycinamide-containing fragments and capped peptide-like units in medicinal chemistry and pharmaceutical intermediate development. Its protected termini (N-acetylated and C-methylamide) provide a controlled end-group environment that can be carried forward into further functionalization or used to generate analog libraries with consistent amide endpoints. Synthetic teams value this form when the goal is to assemble or evaluate glycine-based amide motifs while minimizing side reactions associated with free amino or carboxyl groups.
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