D-2-aminoheptanedioic acid is a D-configured, non-proteinogenic amino acid derivative featuring a seven-carbon backbone bearing two terminal carboxylic acid groups (a diacid) and a primary amino group at the 2-position. The molecule contains both amino and carboxyl functional groups, with the stereochemical descriptor "D" indicating a defined configuration at the chiral 2-carbon, and its diacid side chain provides two sites for salt formation and coordination chemistry. In research and synthesis, it is used as a building block for preparing amino acid-containing linkers, chelating or crosslinkable motifs, and peptide or peptidomimetic structures where a rigid, dicarboxylate functionality and defined stereochemistry are required.
CAT No: CP03502
D-2-Aminoheptanedioic acid is a D-configured amino acid derivative featuring a linear seven-carbon backbone bearing an α-amino group and two carboxylic acid functionalities separated by a methylene unit, enabling strong ionic character and predictable acid-base behavior. The presence of two carboxyl groups supports controlled salt formation, chelation to metal ions, and stepwise functional group manipulation for downstream derivatization. The D-stereocenter provides stereochemical specificity for chiral recognition and for incorporation into stereodefined synthons. As an amino acid-based intermediate, D-2-aminoheptanedioic acid can be converted into protected amino acid derivatives, activated carboxylic intermediates, and polymerizable or conjugatable fragments used in peptide science and fine chemical manufacturing.
1. Peptide Synthesis
D-2-Aminoheptanedioic acid supports peptide coupling chemistry through its α-amino group and carboxyl functionality, with the second carboxyl group enabling orthogonal derivatization strategies for controlled N- and C-terminal construction. The dicarboxylic motif can be protected as an acid-labile or acid-stable derivative to tune reactivity during amide bond formation and subsequent deprotection. D-stereochemistry can be preserved by employing protecting-group schemes that minimize racemization during activation and coupling steps. Peptide building block preparation from D-2-aminoheptanedioic acid can be applied to generate stereodefined peptide analogs and peptidomimetic scaffolds bearing additional carboxyl handles for further functionalization.
2. Amino Acid Derivatization
D-2-aminoheptanedioic acid functions as a platform for amino acid derivatization where dual carboxyl groups allow selective mono-activation, esterification, or conversion to amide derivatives depending on the chosen protecting-group pattern. The α-amino group can be masked as a protected amine to enable controlled transformations of one carboxyl group without perturbing the other, supporting the synthesis of chiral intermediates for medicinal chemistry and materials research. D-configuration provides stereochemical fidelity for chiral ligands, chelating agents, and stereodefined functional fragments used in synthetic organic chemistry. Downstream utility includes preparation of activated acids, carboxylate salts, and conjugation-ready derivatives that retain the amino acid backbone for further assembly.
3. Chelation And Metal Complexation
D-2-aminoheptanedioic acid is well suited for chemical biology and analytical research that require predictable metal binding, since the two carboxylate groups can coordinate to transition metals and alkaline earth ions while the D-stereocenter can influence complex geometry. Acid-base behavior and salt formation enable formulation of stable coordination complexes or calibration reagents where charge state control matters. Carboxylate functionalization derived from this amino acid can be used to tune binding strength and selectivity for spectroscopic detection, chromatography additives, or metal-ion scavenging intermediates. Industrially, metal-chelating derivatives prepared from D-2-aminoheptanedioic acid can serve as process additives or intermediate components in specialty chemical production where controlled sequestration of metal contaminants supports downstream manufacturing consistency.
4. Chiral Building Block Development
D-2-aminoheptanedioic acid provides a stereodefined chiral starting point for developing D-configured amino acid intermediates used in asymmetric synthesis and stereochemical SAR studies. The combination of an α-amino group with a dicarboxylic framework enables conversion into protected amino acid derivatives, N-protected intermediates, and C-terminal modified fragments that maintain D-configuration through carefully selected activation and protection strategies. The second carboxyl group can be leveraged to introduce additional functional handles for conjugation, crosslinking, or scaffold diversification while retaining a chiral center for molecular recognition. Chiral intermediate preparation from D-2-aminoheptanedioic acid can feed into libraries of stereodefined compounds used in fragment-based molecular design and peptide analog construction.
5. Polymer And Material Modification
D-2-aminoheptanedioic acid can be employed in functional materials and polymer modification where the dicarboxylic acid motif enables incorporation into polymer backbones, crosslinking networks, or surface functionalization chemistries. The amino functionality supports coupling to activated polymer sites or formation of amide linkages, while the second carboxyl group can remain available for subsequent grafting, salt formation, or ion-binding interactions. D-stereochemistry can influence polymer microenvironment and stereoregularity when incorporated into stereodefined segments or copolymers. Material-oriented downstream uses include synthesis of ion-responsive coatings, chelating polymer additives, and amino acid-derived crosslinkers that connect amino acid chemistry with applied industrial formulation needs.
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