H-Gly-NHMe*HCl is a glycine-derived amino acid derivative in which the amino terminus is acylated (H-Gly-) and the carboxamide is present as an N-methylamide (-NHMe), with the accompanying hydrochloride indicating formation of an amine salt. The molecule bears a free carboxamide carbonyl and a secondary amide nitrogen, while the "*HCl" denotes protonation/association of a basic site under acidic conditions, which can influence solubility and handling in peptide-related or amide-forming steps. As a protected/activated glycine amide intermediate rather than a free amino acid, it is used in synthetic chemistry and peptide chemistry workflows that require controlled incorporation of a glycinyl unit into larger amide-containing structures or conjugates.
CAT No: CP25861
CAS No:49755-94-4
Synonyms/Alias:2-amino-N-methylacetamidehydrochloride;49755-94-4;H-Gly-NHMeHCl;ACETAMIDE,2-AMINO-N-METHYL-,HYDROCHLORIDE(1:1);AC1Q3BOR;H-Gly-NHMehydrochloride;SCHEMBL719172;2-amino-N-methylacetamideHCl;CTK8B3418;glycinemethylamidehydrochloride;N-methylglycineamidehydrochloride;MolPort-005-310-660;ZYZNZBKTJDYJKQ-UHFFFAOYSA-N;ANW-42489;AKOS008019614;MCULE-1901033297;AK-81266;DA-05469;KB-77762;OR014685;OR273823;KB-114134;FT-0681486;EN300-11782;K-9237
Chemical Name:N-Methyl-glycine amide, 2-Amino-N-methylacetamide hydrochloride
H-Gly-NHMe*HCl is a glycine-based amino acid derivative presented as a hydrochloride salt, featuring an N-methylamide motif (NHMe) on the glycine backbone and a protonated amide salt form that improves handling and aqueous compatibility. The small, achiral glycine core reduces conformational complexity while the N-methylation modulates hydrogen-bonding capacity and peptide-like recognition in coupling and downstream assays. The hydrochloride counterion can influence solubility and can be leveraged to control protonation state during derivatization steps. The resulting structure functions as a compact, amide-containing building block and chiral-synthesis-adjacent intermediate when paired with stereodefined amino acid fragments in peptide or peptidomimetic assembly.
1. Peptide Coupling Chemistry
H-Gly-NHMe*HCl supports peptide synthesis workflows by providing a glycine-derived amide unit that can participate in fragment condensation strategies where an N-methylated amide is desired. The N-methylamide functionality affects acyl transfer reactivity and can be used to tune amide hydrogen-bonding patterns in short peptides and peptidomimetics. The hydrochloride form can facilitate controlled deprotonation and solvation during coupling sequence design, helping maintain consistent reaction conditions across multi-step syntheses. Downstream, the compound can be incorporated into peptide analog scaffolds to generate N-methylated linkages that are compatible with structure-activity relationship studies and synthetic methodology development in peptide chemistry.
2. Peptidomimetics And SAR Studies
H-Gly-NHMe*HCl is suited to peptidomimetic construction where N-methylation serves as a structural modification for modulating backbone conformation and proteolytic stability proxies. The glycine backbone provides a minimal steric profile, enabling systematic variation of neighboring residues while the N-methylamide group changes donor/acceptor balance for molecular recognition. The salt form can be advantageous for preparing defined intermediates for parallel synthesis, including library generation of N-methylated amide-containing fragments used in SAR studies. The compound's amide-bearing architecture supports downstream conversion into longer analogs that can be evaluated through biochemical and analytical binding or stability assays.
3. Chiral Building Block Integration
H-Gly-NHMe*HCl can serve as a glycine-derived chiral-synthesis-adjacent intermediate in routes that assemble stereodefined peptide fragments, even though the glycine center itself is achiral. The N-methylamide unit provides a chemically stable handle for coupling to stereogenic amino acid building blocks, enabling consistent linkage formation adjacent to chiral centers in target molecules. The hydrochloride salt can aid in isolating and transporting the amide-containing fragment with reproducible protonation behavior during sequential coupling and deprotection planning. Integration of this fragment into stereochemically controlled syntheses supports the preparation of defined dipeptide and oligopeptide analogs used in stereochemical mapping and fragment-based molecular design.
4. Analytical Reference Standards
H-Gly-NHMe*HCl is applicable to analytical research as a structurally defined amino acid derivative reference for method development and impurity profiling in amide-containing synthesis streams. The small molecular size and clear functional group composition, including the N-methylamide and protonated amide salt character, can facilitate chromatographic and spectroscopic identification in LC-MS and NMR workflows. The hydrochloride counterion may improve reproducibility of sample preparation for calibration solutions and can help stabilize the protonation state during measurement. Downstream use includes supporting quantitative or qualitative characterization of glycine-derived N-methylamide fragments generated during peptide building block preparation and process chemistry intermediate monitoring.
5. Pharmaceutical Intermediate Preparation
H-Gly-NHMe*HCl can be employed in pharmaceutical manufacturing-oriented intermediate preparation where N-methylated amide motifs are incorporated into drug-like scaffolds and peptide-like inhibitors. The glycine-derived amide structure provides a compact, predictable fragment for assembling larger molecules through sequential coupling, protecting-group strategy planning, and controlled functional group interconversions. The hydrochloride form supports practical handling in multi-step synthesis, particularly when aqueous workups or salt-form manipulations are integrated into process design. Downstream, the compound can feed into fine chemical synthesis of N-methylated linkers and peptide-mimetic intermediates that are compatible with industrial scale-up of amide bond construction chemistry.
6. Industrial Biocatalysis Substrate Design
H-Gly-NHMe*HCl may be used in industrial biocatalysis research and development as a substrate-like amino acid derivative for enzyme screening involving amide-forming or amide-modifying transformations. The N-methylamide functionality provides a defined hydrogen-bonding pattern that can influence enzyme recognition and can be used to probe substrate scope for peptide-related biocatalysts. The glycine backbone enables straightforward incorporation into reaction schemes that generate N-methylated amide products or intermediates for subsequent chemical elaboration. Downstream, enzyme-derived or enzyme-compatible intermediates can be directed toward peptidomimetic construction, analytical reference generation, and process chemistry intermediate preparation, linking amino acid derivative chemistry to applied manufacturing workflows.
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