2-Aminoctanoic acid is a free, non-aromatic aliphatic amino acid featuring an eight-carbon chain with the amino group positioned at the 2-position relative to the carboxyl group, classifying it as a medium-chain, straight-chain amino acid. The molecule bears both a primary amine and a carboxylic acid functional group along the alkyl backbone, with the remaining side-chain portion being predominantly hydrophobic and flexible, which influences its solubility and behavior in peptide and analytical contexts. As an unprotected amino acid, it is used as a building block for preparing modified peptides and amino acid derivatives, and it can serve as a substrate or reference compound in analytical method development such as amino acid profiling and derivatization-based characterization.
CAT No: CP03201
CAS No:644-90-6
Synonyms/Alias:64365-27-1;Ac-Arg-Nh2Salt;SCHEMBL1934309;SCHEMBL14117893;C8H17N5O2;ZINC2560000;6075AH;Pentanamide,2-(acetylamino)-5-[(aminoiminomethyl)amino]-,(2S)-
2-Aminoctanoic acid is a medium-chain aliphatic amino acid featuring a linear eight-carbon framework with a primary amino group and a carboxylic acid, providing a hydrophobic side chain that differs from proteinogenic branched or aromatic residues. Its simple, unprotected functionality makes it a practical building block for preparing amide and peptide-like linkages as well as for constructing hydrophobic segments in polymer and surface chemistry workflows. In synthetic and materials contexts, its straight-chain character is frequently leveraged to tune hydrophobicity, spacing, and backbone flexibility.
1. Hydrophobic Linker Building
2-Aminoctanoic acid is used as a hydrophobic amino acid building block to introduce a flexible aliphatic segment into amide-linked structures, including peptide fragments, peptidomimetic scaffolds, and other nitrogen-containing linkers used in chemical biology and materials R&D. Researchers developing amphiphilic or hydrophobic conjugates often select this residue to control the balance between polar functionality (carboxyl/amine chemistry) and nonpolar surface character (long linear chain), which can influence solubility and self-assembly behavior in downstream formulations. The free amino and carboxylic acid groups enable straightforward incorporation into coupling workflows for generating defined chain lengths and reproducible hydrophobic spacing.
2. Peptidomimetic And Fragment Synthesis
2-Aminoctanoic acid serves as a practical component for constructing peptide-like intermediates and non-natural fragment libraries where a non-proteinogenic, straight-chain side chain is desired for structure-property studies. Medicinal chemistry and chemical biology teams commonly use such amino acid building blocks to probe how increased aliphatic character and backbone flexibility affect conformational preferences and interaction profiles in SAR campaigns, while keeping the functional group pattern compatible with standard amide bond formation strategies. Because the molecule is not inherently constrained by aromatic rings or branching, it is frequently chosen when researchers want a clean hydrophobic contribution without adding additional steric or electronic complexity.
3. Polymer And Biomaterials Functionalization
2-Aminoctanoic acid is applied in biomaterials and polymer chemistry to incorporate hydrophobic amino acid units that can modulate surface character, interfacial behavior, and polymer segment hydrophobicity. Material scientists often use it to prepare amino acid-derived monomers, crosslinking precursors, or pendant-chain components that maintain chemical handle(s) for subsequent coupling or curing steps, enabling more controlled design of hydrophobic domains in coatings, membranes, and scaffold materials. Its linear alkyl chain supports tuning of chain packing and water affinity, which is valuable when designing materials intended for controlled wetting, adsorption studies, or hydrophobic domain patterning in research-grade systems.
4. Analytical And Reference Standards
2-Aminoctanoic acid is also used as an analytical reference material in method development and compositional studies involving amino acid quantification, derivatization-based assays, or LC-MS workflows that require a defined aliphatic amino acid standard. Analytical chemistry teams may include it when validating chromatographic separation of non-proteinogenic amino acids or when building calibration sets that cover longer-chain hydrophobic species. The unprotected, well-defined structure helps ensure reproducible derivatization and consistent response across instrumentation platforms used for amino acid profiling in chemical synthesis monitoring and research sample characterization.
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