D-2-Aminoundecanoic acid is a D-configured, non-proteinogenic amino acid featuring an 11-carbon aliphatic backbone with a primary amino group at the 2-position and a terminal carboxylic acid. The side chain is a long hydrophobic alkyl chain that lacks additional functional groups beyond the amino and carboxyl groups, enabling it to participate in amide formation while maintaining stereochemical identity at the α-carbon. In synthetic and chemical biology workflows, it is used as a building block for preparing amino acid derivatives, constructing hydrophobic peptide analogs, and generating substrates or standards for analytical method development involving amino acid stereoisomers.
CAT No: CP04403
D-2-Aminoundecanoic acid is a chiral, aliphatic amino acid with the stereogenic center at the α-position (D-configuration) and an 11-carbon linear side chain that terminates in a terminal methylene group. The molecule contains a primary amino group and a carboxylic acid, enabling salt formation and controlled reactivity in peptide coupling and derivatization chemistry. The extended hydrophobic chain imparts amphiphilic behavior when converted to protected forms or salts, while the amino and acid functionalities support orthogonal protection strategies for sequential functional group manipulation. As a stereodefined amino acid, it functions as a chiral building block and synthetic intermediate for constructing long-chain amino acid motifs, including incorporation into peptide-like structures and downstream functional materials.
1. Peptide Synthesis
D-2-Aminoundecanoic acid supports peptide building block preparation through its α-amino and α-carboxyl groups, which can be converted into N-protected amino acid derivatives and activated carboxylic acid forms for coupling. The D-stereocenter enables stereochemically defined incorporation into peptide sequences where long aliphatic side chains influence folding, membrane affinity, and hydrophobic packing. The terminal methylene side chain can remain available for later derivatization or be transformed into reactive handles after peptide assembly, enabling stepwise side-chain functionalization. Resulting peptide analogs and peptidomimetic scaffolds can be used in structure-activity relationship studies and biochemical research where chain length and stereochemistry govern molecular recognition.
2. Side-Chain Functionalization
D-2-Aminoundecano acid serves as a long-chain amino acid precursor for side-chain derivatization strategies targeting the terminal alkyl functionality. The hydrophobic eleven-carbon framework can be functionalized into alkyl halides, azides, alkenes, or other electrophilic/handle-bearing intermediates, while the amino acid backbone can be protected to maintain chemoselectivity during transformation. Orthogonal protection of the amino and carboxyl groups allows selective modification of the side chain without premature peptide coupling or decarboxylation. The resulting functionalized derivatives can be employed for downstream conjugation chemistry, polymerizable monomer generation, and creation of amphiphilic or lipophilic probes for chemical biology workflows.
3. Chemical Biology Conjugation
D-2-Aminoundecanoic acid can be applied to biomolecule modification and chemical biology labeling strategies by providing a stereodefined amino acid handle for linker construction. The primary amino group and carboxyl group facilitate conversion into activated intermediates, including amide-forming or coupling-ready derivatives, that can be attached to proteins, peptides, or polymer backbones. The D-configuration can help control stereochemical outcomes in linker architecture, which can influence binding orientation and stability in conjugates. Long-chain hydrophobic character supports membrane-associated labeling concepts and amphiphile-like conjugate design, enabling preparation of labeled reagents, affinity probes, and peptide-based chemical tools.
4. Chiral Building Block Intermediate
D-2-Aminoundecanoic acid functions as a chiral amino acid intermediate for stereoselective synthesis of D-configured derivatives and long-chain chiral scaffolds. The α-amino acid stereocenter enables downstream formation of N-protected amino acid esters, amides, and activated acids used in iterative synthetic sequences. The linear aliphatic side chain provides a structural motif that can be carried through multiple transformations, supporting the construction of chiral auxiliaries, ligands, and intermediate fragments for fine chemical synthesis. The molecule's defined stereochemistry also supports analytical method development for chiral separation and characterization of amino acid derivatives and peptide intermediates.
5. Pharmaceutical Manufacturing Intermediate
D-2-Aminoundecanoic acid can be incorporated into industrial process chemistry as a feedstock for producing long-chain amino acid derivatives used in manufacturing of peptide-like intermediates and specialty chemical building blocks. The amino acid's functional groups allow conversion into protected forms compatible with standard peptide coupling operations and controlled deprotection steps, supporting scalable synthesis planning. The hydrophobic chain length can be leveraged to tune solubility, crystallization behavior, and hydrophobicity of intermediates and final materials, which are relevant considerations in downstream manufacturing. The compound's role as a chiral, stereodefined precursor enables consistent intermediate quality for producing structured linkers, peptidomimetic fragments, and other amino acid-derived components used in applied chemical production.
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