L-α-aminoadipic acid is a naturally occurring α-amino acid featuring an amino group on the α-carbon and a terminal carboxylic acid separated from the backbone by a three-carbon chain, placing it in the amino dicarboxylic acid class. The molecule contains two carboxyl functional groups and one primary amino functional group, with stereochemistry specified as L at the α-carbon, enabling it to exist as a zwitterion under neutral conditions and to form salts or engage in acid-base equilibria during handling and coupling. In peptide and amide synthesis, L-α-aminoadipic acid is used as a building block or precursor for preparing amino acid derivatives, enabling incorporation of the extended dicarboxyl side chain into peptides and related structure-activity or labeling studies.
CAT No: CP02702
CAS No:1118-90-7
Synonyms/Alias:L-2-Aminoadipicacid;(S)-2-aminohexanedioicacid;1118-90-7;(2S)-2-aminohexanedioicacid;L-Homoglutamicacid;L-alpha-Aminoadipicacid;l-a-aminoadipicacid;L-2-Aminoadipate;L-alpha-Aminoadipate;UNII-88ZH74L7SR;Aminoadipate;CHEMBL88804;CHEBI:37023;L-2-Aminohexanedioate;Adipicacid,2-amino-;(S)-2-Aminoadipicacid;alpha-Aminoadipicacid,DL-;EINECS210-960-4;homoglutamicacid;h-aad-oh;UN1;h-2-aad-oh;h-l-2-aad-oh;AmbotzHAA1089;l-a-aminohexanoicacid
L-α-Aminoadipic acid is the L-configured amino acid bearing a chiral α-carbon and a side chain that terminates in a second carboxylic acid, yielding a dicarboxylic amino acid framework with two acidic functional groups and a primary amino group. The molecule's zwitterionic character in aqueous media and its strong hydrogen-bonding capacity make it a practical handle for salt formation, controlled protection, and stepwise functional group manipulation. Carboxyl groups can be selectively protected as esters or acyl derivatives, while the amino group can be protected as carbamates or amides to enable orthogonal coupling chemistries. This structural combination supports its use as a chiral building block and as a downstream intermediate for peptide-related synthesis, heterocycle construction, and industrial fine-chemical routes requiring a stereodefined amino acid scaffold.
1. Peptide Synthesis
L-α-aminoadipic acid supports peptide building-block workflows where a dicarboxylic side chain enables incorporation of an additional acidic functionality into peptide backbones and peptidomimetics. The α-amino and α-carboxyl groups participate in standard peptide coupling after appropriate protection strategies, while selective side-chain carboxyl protection can prevent intramolecular side reactions and improve coupling selectivity. Orthogonal protection of both carboxyl groups and the amino group enables controlled generation of mono- or di-functional peptide analogs for fragment assembly and sequential elongation. L-α-aminoadipic acid can therefore serve as a stereodefined intermediate for constructing acidic peptide motifs, peptide conjugation handles, and amino acid-derived scaffolds used in biochemical research and synthetic methodology development.
2. Amino Acid Derivatization
L-α-aminoadipic acid is suitable for amino acid derivatization programs targeting functional group transformation of its two carboxylic acids and primary amino group. Esterification of one or both carboxyl groups can tune solubility and reactivity, while conversion to activated esters or amides enables downstream formation of amide-linked derivatives and polymerizable monomers. Amino protection as a carbamate or acylated amide can allow selective activation of carboxyl groups for sequential derivatization, supporting the synthesis of chiral intermediates for SAR studies and chemical biology probes. L-α-aminoadipic acid thus functions as a chemically tractable chiral amino acid intermediate for producing functionalized derivatives used in fine chemical synthesis and applied materials chemistry.
3. Heterocycle And Scaffold Building
L-α-aminoadipic acid can be applied in heterocycle synthesis where the bifunctional carboxylate array and stereodefined amino group enable intramolecular cyclization strategies. Side-chain carboxyl functionality can be activated to form amide or ester intermediates that participate in ring-forming steps, while amino protection can regulate chemoselectivity during scaffold assembly. The resulting cyclic or fused nitrogen-containing frameworks can be used as chiral fragments in medicinal chemistry research, including peptidomimetic core construction and fragment-based molecular design. L-α-aminoadipic acid therefore serves as a stereochemical precursor for generating amino acid-derived ring systems and chiral building blocks relevant to synthetic organic chemistry and downstream library synthesis.
4. Chemical Manufacturing Intermediates
L-α-aminoadipic acid is relevant to process chemistry intermediate preparation due to its well-defined functional group pattern that supports salt formation, protection/deprotection planning, and controlled activation in multistep manufacturing routes. The presence of two carboxylic acids allows conversion into protected acids, activated carboxyl derivatives, or amide-forming intermediates that can be routed into downstream specialty chemicals and industrial intermediates. Protection-group strategies such as carboxyl esterification and amino acylation can be employed to manage reactivity during sequential transformations, reducing undesired cross-reactivity between acidic groups. L-α-aminoadipic acid can thus be used as a chiral starting material for industrial fine chemical synthesis where stereodefined amino acid chemistry and scalable intermediate design are required.
5. Analytical Standards and Metabolite Studies
L-α-aminoadipic acid can be utilized in analytical research as a reference standard for amino acid profiling and method development involving dicarboxylic amino acid species. The defined L-stereochemistry and characteristic ionization behavior support chromatographic and mass spectrometric identification when used alongside derivatization workflows that target amino and carboxyl functionalities. Carboxyl protection or derivatization can generate stable analytical forms for calibration, enabling consistent quantitation in studies that monitor amino acid transformations and related biochemical pathways. L-α-aminoadipic acid therefore functions as a chemically defined analytical and biochemical research intermediate supporting robust measurement and downstream interpretation in applied laboratory and industrial quality testing contexts.
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