(6R,2S)-Diaminopimelic acid is a naturally occurring, non-proteinogenic amino acid derivative of the diaminocarboxylic acid class featuring a six-carbon backbone with two amino substituents and a terminal carboxylic acid. The molecule bears an amino group at the 2-position and a second amino group at the 6-position, and its name specifies the (6R,2S) stereochemical configuration around the relevant stereocenters, which governs the three-dimensional arrangement of its basic side-chain functionality. It is used as a chemical building block for peptide and peptidomimetic synthesis and for structure-activity or enzyme-substrate studies that rely on diaminated amino acid side chains, as well as for preparing more complex amino acid derivatives and analytical standards.
CAT No: CP05602
CAS No:922-54-3
Synonyms/Alias:(2R,6S)-2,6-diaminoheptanedioicacid;922-54-3;meso-2,6-Diaminopimelicacid;meso-diaminoheptanedioate;CHEBI:16488;(R*,S*)-2,6-Diaminoheptanedioicacid;meso-A2pm;DIAMINOPIMELICACID;Heptanedioicacid,2,6-diamino-,(R*,S*)-;meso-diaminoheptanedioicacid;6-CARBOXYLYSINE;meso-2,6-diaminoheptanedioate;meso-diaminopimelate;(6R,2s)-diaminopimelicacid;C7H14N2O4;meso-1-alpha,epsilon-diaminopimelate;meso-DAP;meso-diaminopimelicacid;meso-diaminopimeilicacid;AC1Q5QLM;6CL;AC1L40SH;SCHEMBL29291;CHEMBL415306;GTPL5021
(6R,2S)-Diaminopimelic acid is a stereochemically defined diaminocarboxylic acid featuring two amino groups and a terminal carboxylic acid, making it a structurally distinctive building block for peptide and peptidomimetic chemistry. Its rigid, defined stereocenters support reproducible incorporation into synthetic sequences used in biochemical tool development and structure-function studies. Researchers also use this compound as a chemically characterized amino acid standard in analytical workflows where the presence of multiple amines enables targeted derivatization and mass spectrometric readouts.
1. Peptidomimetic Building Block
(6R,2S)-Diaminopimelic acid is used as a specialized amino acid building block for constructing peptidomimetic scaffolds and defined peptide fragments in chemical biology and medicinal chemistry programs. The presence of two amino functionalities supports downstream derivatization strategies that enable controlled side-chain chemistry during library synthesis, including formation of amide-linked analogs and incorporation into constrained amine-rich motifs. This makes the compound valuable for researchers developing structure-activity relationship (SAR) series where stereochemistry and amine density are critical for matching binding-site or recognition features in target biomolecular assays.
2. Crosslinking And Multi-amine Chemistry
(6R,2S)-Diaminopimelic acid is applied in workflows that require a diamine-bearing linker or intermediate for amine-to-amine coupling chemistry. In biomaterials and protein chemistry research, its dual amino groups can be leveraged to generate defined amine-reactive intermediates or to introduce amine-rich handles into synthetic constructs used for conjugation studies and material functionalization. Teams working on protein modification, surface attachment chemistry, or polymer conjugates often select this type of diaminocarboxylic acid because it provides a straightforward route to multi-functional amine content while maintaining a defined stereochemical framework for reproducible batch-to-batch performance.
3. Analytical Derivatization Standard
(6R,2S)-Diaminopimelic acid is frequently used as an analytical reference material for method development and quantification in amino acid profiling workflows. Because it contains multiple primary amines alongside a carboxylate, it is well-suited to derivatization-based LC methods and targeted MS approaches that separate and detect amine-containing analytes with improved chromatographic behavior. Analytical chemistry groups use this compound to calibrate instrument response, validate sample preparation steps, and support identification of diaminocarboxylic acid species in complex matrices where stereodefined standards improve confidence in peak assignment and quantitation.
4. Pharmaceutical Intermediate Development
(6R,2S)-Diaminopimelic acid is used as a stereochemically defined intermediate in the synthesis of specialized nitrogen-rich intermediates for pharmaceutical and agrochemical research chemistry. Medicinal chemistry and process development teams incorporate such diaminocarboxylic acid motifs into advanced intermediates that later undergo functional group interconversions to reach final heterocycle or amide-rich targets. The compound's well-defined stereochemistry and dual amine functionality make it particularly useful when the downstream route requires retention of stereochemical integrity and controlled introduction of nitrogen functionalities into the growing synthetic sequence.
1. The spatiotemporal control of signalling and trafficking of the GLP-1R
2. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More