(8S,2R)-Diaminononanedioic acid is a non-proteinogenic, dicarboxylic amino acid derivative featuring a nine-carbon backbone bearing two amino substituents and two carboxylic acid groups, classifiable as a diamino-substituted amino acid with a long aliphatic chain. Its stereochemical descriptors (8S,2R) specify the relative configuration at the indicated stereocenters, and the molecule presents both amine and carboxyl functionalities that can exist as zwitterionic and salt forms depending on pH, while also providing multiple sites for selective derivatization. In research settings, it is used as a chemically defined building block for preparing polyamide or peptide-like structures, for constructing constrained or multi-functional linkers, and for analytical or chemical-biology studies requiring a long-chain diamino-dicarboxyl motif.
CAT No: CP05703
CAS No:59014-27-6
Synonyms/Alias:Bestatin;Ubenimex;58970-76-6;(S)-2-((2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido)-4-methylpentanoicacid;Ubenimexum[Latin];N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine;CHEMBL29292;Bestatin,Ubenimex;EINECS261-529-2;NK421;NK-421;NSC265489;BRN4704312;([2S,3R]-3-Amino-2-hydroxy-4-phenylbutanoyl)-L-leucine;[(2s,3r)-3-amino-2-hydroxy-4-phenylbutanoyl]-l-leucine;ST50405897;(3-Amino-2-hydroxy-4-phenylbutanoyl)-L-leucine;3-(R)-Amino-2-(S)-hydroxy-4-phenylbutanoyl-(S)-leucine;(-)-N-((2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl)-L-leucine;(S-(R*,S*))-N-(3-Amino-2-hydroxy-4-phenylbutyroyl)-L-leucine;L-Leucine,N-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-,(S-(R*,S*))-;SMR000059165;Ubenimexum;Ubestatin;2-(3-AMINO-2-HYDROXY-4-PHENYL-BUTYRYLAMINO)-4-METHYL-PENTANOICACID
(8S,2R)-Diaminononanedioic acid is a chiral, diamino-functionalized dicarboxylic amino acid building block featuring a long aliphatic chain and two stereogenic features (8S,2R). Its two carboxylic acid groups and primary amine functionality make it well suited for constructing polyamide- and peptide-like architectures, as well as for preparing defined, rigidified linkers in chemical biology and materials chemistry workflows. Researchers commonly use this scaffold to introduce a controlled diamino/dicarboxyl motif for stepwise coupling, polymer segment design, and structure-defined conjugate or intermediate synthesis.
1. Polyamide And Peptide Linkers
(8S,2R)-Diaminononanedioic acid is used as a structural building block for preparing amide-rich polymers and peptide-like linkers where a long, flexible aliphatic spacer is required between reactive termini. In polymer chemistry and specialty materials research, its two carboxyl groups enable incorporation into step-growth coupling strategies to form repeat units with predictable spacing, while the diamino functionality supports defined branching or end-group functionalization after coupling. Medicinal chemistry and chemical biology groups also value this motif when designing linker elements for multicomponent constructs, because the diamino/dicarboxyl pattern supports downstream derivatization into amide or salt-form intermediates that remain compatible with subsequent conjugation steps.
2. Bioconjugation Intermediate Synthesis
(8S,2R)-Diaminononanedioic acid serves as a practical intermediate for generating defined diamino-containing linkers used in bioconjugation workflows. In protein chemistry and chemical biology laboratories, the compound's primary amine and dicarboxyl functionality supports conversion into activated coupling forms that can be used to attach biomolecules or biomolecule-derived scaffolds through amide bond formation or controlled salt/derivative preparation prior to conjugation. The long chain length and chiral configuration help maintain a consistent spatial presentation of the reactive handle, which is particularly useful when preparing linker-defined conjugates for binding studies, reagent standardization, or controlled assembly of multivalent biomolecular systems.
3. Chiral Building Block For SAR Studies
(8S,2R)-Diaminononanedioic acid is frequently selected as a chiral amino acid intermediate for structure-activity relationship (SAR) development in peptidomimetic and linker-focused medicinal chemistry programs. Its stereochemical definition (8S,2R) allows chemists to probe how stereochemistry and linker geometry influence the properties of amide-linked analogs, including conformational preferences and the spatial arrangement of functional groups in larger scaffolds. Because the molecule contains both amine and carboxyl functionalities, it can be routed into a series of closely related derivatives for parallel synthesis campaigns, helping teams generate structure-defined analog sets for downstream characterization by LC-MS, NMR, and chromatographic profiling.
4. Analytical Standard And Calibration Chemistry
(8S,2R)-Diaminononanedioic acid is used in analytical method development and calibration workflows where a defined, chiral diamino/dicarboxylic reference material is required. In analytical chemistry and quality control settings, laboratories may employ it as a structural standard for verifying derivatization efficiency, monitoring coupling-related impurities, or supporting method qualification when analyzing amino acid-derived intermediates and amide-linked products. The presence of multiple functional groups also makes it useful for preparing consistent standards or reference derivatives that reflect the chemical environment of linker fragments used in peptide and polymer synthesis.
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