DL-2,8-Diaminononanedioic acid is a non-proteinogenic, diamino-dicarboxylic amino acid derivative featuring a nine-carbon backbone bearing two terminal carboxylic acid groups and two amino substituents at the 2- and 8-positions. The molecule contains both primary amine functionalities and carboxylic acid groups, and the "DL" designation indicates a racemic mixture without specifying a single stereochemical configuration. In synthesis and chemical biology workflows, it is used as a bifunctional building block for preparing polyamine-carboxylate frameworks, crosslinker-like linkers, and peptide or peptidomimetic analogues where two amino sites and two acid groups provide defined coordination and conjugation handles for further derivatization.
CAT No: CP05701
CAS No:98951-66-7
Synonyms/Alias:2,8-Diaminononanedioicacid;98951-66-7;NSC133392;AC1L5TH7;DL-2,8-Diaminononanedioicacid;SCHEMBL4848672;STOCK1N-27724;CTK7D4154;nonanedioicacid,2,8-diamino-;DL-2,8-Diaminononanedioicacid;MolPort-002-514-692;6930AC;ANW-63281;STK679938;AKOS001740333;MCULE-1750659514;NSC-133392;AK-87785;AM004696;KB-226285;ST4080922;TC-152026;A2945/0124045
DL-2,8-Diaminononanedioic acid is a diamino-substituted dicarboxylic amino acid derivative with the formula HOOC-(CH2)7-NH2 at both ends, featuring two primary amine groups and two carboxylic acid functionalities distributed along a flexible aliphatic chain. The molecule exists as a DL mixture at the stereochemical level where applicable to its conformationally defined intermediates, and it can be treated as a bifunctional scaffold for stepwise derivatization and salt formation. Carboxylic acids enable controlled activation for amide formation, while the diamines support orthogonal protection strategies to direct selective coupling, cyclization, or conjugation. The combination of multiple reactive heteroatoms makes it a practical intermediate for building peptidic and polyamide-like structures, as well as for preparing functional chelators and polymerizable monomers.
1. Polyamide And Polymer Building
DL-2,8-Diaminononanedioic acid is used in polymer and specialty material manufacturing contexts where diamine and dicarboxylic acid functionality enables step-growth polycondensation to form nylon-like polyamides or related amide-rich backbones. The linear aliphatic chain length and the presence of two terminal carboxyl groups support predictable incorporation into high-molecular-weight networks, while the two primary amines can be used for downstream crosslinking or post-functionalization. Orthogonal protection of one amine relative to the other can be applied to tune monomer reactivity in sequential synthesis routes, including controlled formation of amide linkages or end-group modification. Downstream utility includes preparation of polymer intermediates, reactive monomers for specialty resins, and chemical manufacturing feedstocks that translate amino acid chemistry into industrial polymer synthesis.
2. Chelator And Coordination Chemistry
DL-2,8-Diaminononanedioic acid is applied in coordination chemistry and analytical research where the diamine and carboxylate groups can coordinate metal ions to form stable chelate frameworks. The two primary amines provide nitrogen donor sites, and the dicarboxylate moieties can generate multidentate binding modes after activation or deprotonation, enabling pH-dependent coordination behavior relevant to method development and materials processing. Selective derivatization of one functional group set, such as masking an amine while leaving carboxylates available, can support controlled formation of mono- or bis-functional ligands for metal-binding studies. Resulting downstream products include metal-complexing ligands, chelation reagents for separations chemistry, and chelator-functionalized intermediates that connect amino acid-derived scaffolds to coordination-driven applications.
3. Bioconjugation Linker Synthesis
DL-2,8-Diaminononanedioic acid is utilized in chemical biology and bioconjugation workflows as a flexible linker precursor for attaching biomolecule-reactive handles through amide coupling and amine-based conjugation. The compound's two carboxylic acids can be activated to form amide bonds with amine-bearing partners, while the diamine groups can be protected to enable selective introduction of one conjugation site at a time. Protecting-group strategies such as orthogonal N-protection allow controlled generation of mono-functionalized derivatives that can be used to build conjugates for labeling, affinity reagents, or immobilization onto solid supports. Downstream derivative formation includes linker reagents for peptide and protein conjugates, immobilization chemistries for affinity chromatography media, and amino acid-based intermediates that support reproducible coupling chemistry.
4. Peptidomimetic And Amide Scaffold Construction
DL-2,8-Diaminononanedioic acid is applied in peptidomimetic and synthetic organic chemistry to construct amide-rich scaffolds that mimic peptide connectivity while introducing defined spacing from the aliphatic chain. The dicarboxylic acid functionality supports conversion into activated acid derivatives for stepwise amide bond formation, while the diamines enable further N-substitution to tune solubility, charge, and intramolecular hydrogen-bonding patterns. Selective protection of one amine relative to the other can direct sequential coupling to generate mono- or di-substituted analogs, supporting structure-activity relationship studies that probe how linker length and functional group placement affect molecular recognition. Downstream utility includes preparation of peptidomimetic building blocks, cyclic or linear amide architectures, and research intermediates that translate amino acid-derived functionality into modular synthetic scaffolds.
5. Protected Intermediate Preparation
DL-2,8-Diaminononanedioic acid is used as a starting material for protected amino acid derivative synthesis where controlled masking of amines and/or carboxyl groups enables selective transformations in multi-step routes. The presence of two primary amines and two carboxylic acids supports orthogonal protection designs that can separate chemoselective steps such as amide formation, carbamate installation, or selective deprotection for iterative coupling. The flexible aliphatic backbone can be leveraged to create defined bifunctional intermediates for downstream fragment assembly, including coupling partners for peptide-like oligomers and polymerizable units. Resulting downstream products include N-protected and selectively functionalized intermediates suitable for fine chemical synthesis, process chemistry intermediate preparation, and manufacturing-oriented production of amino acid-derived building blocks.
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