N-beta-Aminoethyl-Gly-OH is a glycine-based amino acid derivative in which the side chain bears an additional β-aminoethyl substituent, yielding a primary amine functionality alongside the amino acid backbone. The molecule contains an α-amino group and a carboxylic acid (-CO2H) for zwitterionic behavior in aqueous media, and the extra β-amino group provides a second basic site that can participate in salt formation and amide or urea bond formation after appropriate activation. As a bifunctional building block, it is used in peptide and linker synthesis and in chemical biology workflows requiring a primary amine handle for conjugation, crosslinking, or preparation of more complex amino acid and peptide derivatives.
CAT No: CP26849
CAS No:24123-14-6
Synonyms/Alias:N-(2-Aminoethyl)glycine;24123-14-6;2-((2-Aminoethyl)amino)aceticacid;N-beta-aminoethyl-Gly-OH;2-(2-aminoethylamino)aceticacid;AEGEthylenediamine-N-aceticAcid;Ethylenediamine-N-monoaceticAcid;2-[(2-aminoethyl)amino]aceticacid;[(2-AMINOETHYL)AMINO]ACETICACID;Aminoethylglycine;H-Aeg-OH;(2-Aminoethyl)glycine;AC1L8MHM;25240-38-4;N--Aminoethyl-Gly-OH;N-(2'-Aminoethyl)glycine;Glycine,N-(2-aminoethyl)-;SCHEMBL25747;ACMC-209g93;CTK4F2959;MolPort-006-392-101;PIINGYXNCHTJTF-UHFFFAOYSA-N;ANW-25333;MFCD00144824;ZINC19366971
N-beta-Aminoethyl-Gly-OH is an amino acid derivative featuring a glycine core bearing an additional beta-aminoethyl side chain, providing two primary amine functionalities and a carboxylic acid for salt formation and controlled reactivity. The molecule's flexible aliphatic linker and terminal amino group enable straightforward functional group interconversions and nucleophilic participation in amide, urea, and carbamate-forming reactions. As a chiral center is not inherent to the glycine backbone, stereochemical control is typically addressed through downstream derivatization choices rather than intrinsic stereogenicity. The presence of both an aminoethyl amine and a carboxyl group makes N-beta-Aminoethyl-Gly-OH a practical intermediate for constructing polyamine-like motifs and for preparing peptide-compatible building blocks through temporary protection strategies.
1. Peptide Synthesis
N-beta-Aminoethyl-Gly-OH supports peptide coupling chemistry by presenting a carboxylic acid for activation and an amino group that can be selectively protected to control N-terminus reactivity. The beta-aminoethyl side chain can be maintained as a free amine for post-coupling diversification or protected to prevent side reactions during standard coupling to activated carboxyl partners. N-beta-Aminoethyl-Gly-OH can be used to generate peptide building blocks that introduce aminoethyl functionality into peptide backbones or side-chain scaffolds, enabling incorporation of polyamine-like handles for subsequent conjugation. Downstream derivatization can yield aminoethyl-functional peptide analogs suitable for structure-activity relationship studies and biochemical probe construction in peptide science.
2. Chemical Biology Probes
N-beta-Aminoethyl-Gly-OH is well suited to chemical biology workflows that require amine-bearing linkers for probe assembly and biomolecule labeling chemistry. The terminal primary amine and carboxyl group enable formation of amide or carbamate linkages to attach fluorophores, affinity tags, or reactive handles while preserving a defined linker length from the glycine unit. Protecting-group strategies such as transient N-protection can help isolate mono-functional derivatives for controlled conjugation to proteins, nucleic acids, or cell-surface targets. The resulting labeled or derivatized constructs serve as molecular tools for studying binding interfaces, trafficking pathways, and interaction kinetics using amino acid-derived linkers.
3. Bioconjugation Linkers
N-beta-Aminoethyl-Gly-OH functions as a bioconjugation intermediate where its dual-functional amino and acid functionality can be converted into coupling-ready reagents for attaching biomolecules under amide-forming or carbamate-forming conditions. The beta-aminoethyl side chain provides a flexible spacer that can reduce steric constraints during conjugation, which is relevant for maintaining recognition by antibodies, enzymes, or receptor-binding ligands. Selective protection of one amine while activating the carboxyl group can enable stepwise synthesis of mono-substituted conjugates with controlled stoichiometry. The downstream products include aminoethyl-terminated linkers for constructing conjugates used in biochemical research, assay development, and analytical labeling.
4. Polyamine Motif Building
N-beta-Aminoethyl-Gly-OH enables synthesis of polyamine-like motifs by acting as a chiral-agnostic amino acid precursor that contributes an aminoethyl unit and a glycine-derived carboxyl handle for iterative functionalization. The primary amines can be transformed into amides, ureas, or sulfonamides to tune hydrogen-bonding patterns and reactivity toward subsequent cyclization or crosslinking steps. Carboxyl activation allows attachment to electrophiles or incorporation into larger scaffolds, including dendritic or multivalent architectures that benefit from multiple amine sites. The resulting amino acid-derived intermediates can be applied in synthetic organic chemistry and applied materials research where amine-rich functionality supports binding, surface modification, or controlled network formation.
5. Process Chemistry Intermediate
N-beta-Aminoethyl-Gly-OH is applicable to process chemistry and fine chemical synthesis as a robust amino acid derivative feedstock for producing protected aminoethyl-containing intermediates at scale. The carboxylic acid supports predictable salt formation and activation chemistry, while the amine functionality permits controlled protection/deprotection sequences to manage chemoselectivity in manufacturing routes. The flexible aliphatic linker and primary amine reactivity can be leveraged to design downstream intermediates for peptide building blocks, specialty reagents, and functionalized amine-containing chemicals. The compound's straightforward functional group inventory makes it suitable for integration into industrial intermediate preparation where consistent handling of amino acid-derived functionalities is required.
6. Analytical Standards Development
N-beta-Aminoethyl-Gly-OH can be employed in analytical research as a reference material or derivatization substrate for quantifying amino acid derivatives and monitoring reaction mixtures involving aminoethyl-containing products. The presence of both an amino group and a carboxylic acid allows conversion into detectable derivatives using common derivatization strategies that target primary amines or carboxylates, supporting LC or GC method development. Protecting-group-controlled derivatives can also serve as standards for distinguishing mono- versus di-functionalized species in peptide coupling or bioconjugation reaction workflows. The ability to generate well-defined amino acid-derived derivatives makes N-beta-Aminoethyl-Gly-OH relevant for method validation, impurity profiling, and quality control-oriented analytical method development.
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