L-2-aminoheptanedioic acid is a naturally occurring amino acid derivative classified as an aliphatic, dicarboxylic amino acid, featuring a seven-carbon backbone bearing both an amino group and two carboxylic acid functionalities. The molecule contains an L-stereocenter at the alpha position relative to the amino group and presents a flexible side chain with additional carboxyl functionality that can participate in metal coordination and pH-dependent acid-base equilibria, while the amino and carboxyl groups remain available for salt formation or derivatization. In biochemical and synthetic workflows, it is used as a defined building block or substrate analogue for peptide and peptidomimetic synthesis, as well as for studying structure-property relationships involving dicarboxylate-bearing amino acid motifs.
CAT No: CP03503
L-2-aminoheptanedioic acid is an L-configured amino acid with a seven-carbon backbone bearing an α-amino group and a terminal dicarboxylic acid motif, enabling strong, pH-dependent ionic interactions and predictable coordination to metal centers. The molecule contains two carboxylic acid functionalities that can be selectively activated for amide or ester formation while the amino group participates in coupling chemistry under standard peptide and carboxyl activation conditions. The stereogenic center at the α-position provides stereochemical control for downstream syntheses, including formation of chiral amide linkages and incorporation into longer carbon frameworks. As an amino acid-based diacid, it functions as a chemically robust intermediate for amino acid derivatization, protected amino acid chemistry, and downstream scaffold construction in both research and industrial fine-chemical workflows.
1. Peptide Coupling Intermediate
L-2-aminoheptanedioic acid supports peptide synthesis and peptide-like scaffold assembly through its α-amino group and carboxylic acid functionality, which can be converted into activated species for amide bond formation. The presence of two carboxyl groups enables C-terminal and side-chain or tether-like derivatization strategies, where selective protection or activation can direct coupling to a specific terminus. L stereochemistry can be retained through standard coupling/activation sequences, providing a defined chiral center for subsequent fragment condensation. The resulting diacid-bearing peptide building blocks and peptide analog precursors can be used to generate structured libraries for method development and structure-function studies in amino acid chemistry.
2. Side-Chain Functionalization
L-2-aminoheptanedioic acid serves as a diacid-containing platform for side-chain functionalization and tether engineering in synthetic organic chemistry. The two carboxyl groups can be transformed into amides, esters, anhydrides, or activated derivatives, enabling controlled introduction of polar handles for solubility tuning, crosslinking, or binding-site design. The α-amino group can be protected during multi-step sequences, allowing orthogonal transformations that separate amino protection from carboxyl activation and downstream conjugation. Chiral retention at the α-carbon supports stereodefined products, which can be carried into peptidomimetic construction, polymerizable monomer design, or intermediate preparation for functional materials.
3. Chiral Building Block Synthesis
L-2-aminoheptanedioic acid functions as a chiral amino acid intermediate for stereoselective synthesis of complex, diacid-containing molecules. The L configuration provides a defined stereochemical element that can be preserved when converting the amino group to protected forms or when forming amide linkages that lock the chiral center into the target framework. Dual carboxyl functionality supports iterative derivatization, such as sequential activation to build longer chain motifs, introduce reporter groups, or prepare ligands for coordination chemistry. Downstream products can be used as chiral fragments in asymmetric synthesis planning, including routes that require a reliable chiral diacid precursor for fine chemical production.
4. Bioconjugation Linker Chemistry
L-2-aminoheptanedioic acid can be applied in bioconjugation and chemical biology workflows as a diacid-based linker precursor that supports controlled attachment chemistry. The amino group and carboxyl groups allow conversion to coupling-ready intermediates for amide formation with activated biomolecule-reactive groups, while the diacid motif can improve aqueous compatibility and influence local charge during conjugation. Selective protection and deprotection strategies can be used to manage chemoselectivity between the two carboxyl functionalities and the amino group, supporting reproducible linker architecture. The resulting conjugation-ready derivatives can be used to prepare labeled biomolecule constructs, affinity probes, or peptide-based reagents for studying molecular recognition and biomolecular interactions.
5. Process Chemistry Intermediate
L-2-aminoheptanedioic acid is suitable for process chemistry intermediate preparation in industrial fine-chemical and specialty chemical manufacturing contexts. The diacid structure provides multiple handles for downstream conversion into salts, activated esters/amides, or polymerizable derivatives, supporting scalable synthetic route design and downstream formulation flexibility. The molecule's stereochemical integrity at the α-carbon can be maintained through protection-group strategies that separate amino reactivity from carboxyl activation, aligning with manufacturing needs for predictable impurity profiles and controlled transformations. Industrial use can include serving as a feedstock for amino acid derivatization, chiral intermediate supply, and production of diacid-containing specialty building blocks used in chemical manufacturing and applied material synthesis.
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