L-2-Aminoundecanoic acid is a naturally occurring, proteinogenic amino acid analogue with an eleven-carbon aliphatic backbone and a primary amino group positioned at the 2-position relative to the terminal carboxyl group, classifying it as a long-chain aliphatic amino acid. The molecule bears a free α-amino functionality and a free α-carboxylic acid functionality, with the side chain forming a hydrophobic, flexible alkyl chain that can influence solubility and conformational preferences in peptide contexts; the "L-" designation indicates a specific stereochemical form at the α-carbon. As a free amino acid, it is used as a building block for peptide and amide synthesis and for structure-property studies where long-chain hydrophobic side chains are incorporated to tune molecular packing, surface interactions, or analytical derivatization behavior.
CAT No: CP04402
L-2-Aminoundecanoic acid is an aliphatic, chiral amino acid with a long C11 carbon chain that supports hydrophobic interactions while presenting a primary amino group at the C2 position and a carboxylic acid functionality at the corresponding stereogenic carbon backbone. The molecule's extended methylene segment increases lipophilicity and can promote membrane-associated behavior in chemical biology contexts, while the amino acid motif enables standard peptide coupling chemistries after appropriate activation of the carboxyl group. The stereochemistry at C2 (L-configuration) provides defined chiral recognition for enantioselective synthesis and for incorporation into peptide-like structures. The free amino acid can be selectively protected as an N-protected derivative and converted into activated esters or acylating intermediates, making it a practical chiral building block for downstream functionalization and synthetic intermediate preparation.
1. Protected Amino Acid Synthesis
L-2-Aminoundecanoic acid is commonly routed through protected amino acid chemistry to enable controlled N-terminal reactivity during peptide building block preparation. The primary amino group can be converted into an N-protected form (for example, carbamate or amide-protecting strategies) while the carboxylic acid is maintained for selective activation, supporting orthogonal protection patterns used in multi-step syntheses. Long-chain aliphatic character can influence solubility and coupling conditions, so N-protection and carboxyl activation strategies are frequently selected to maintain workable reactivity profiles. The resulting protected amino acid derivative can then be used as a chiral intermediate for N-alkylation, acylation, or incorporation into larger amide frameworks, supporting both research-grade peptide synthesis and industrial fine chemical workflows.
2. Peptide Coupling Chemistry
L-2-Aminoundecanoic acid is suitable for peptide synthesis and fragment assembly where an aliphatic, hydrophobic side-chain contributes to helix stabilization and membrane-mimetic properties in peptide analogs. The amino acid contains both an amino nucleophile and a carboxylic acid that can be transformed into activated carboxyl derivatives, enabling amide bond formation with protected amino acid residues or peptide fragments. The L-configuration at the 2-position provides stereochemical fidelity when incorporated into growing peptide chains, supporting consistent conformational outcomes in peptidomimetic design. Downstream, the long alkyl chain can be used to construct amphiphilic sequences, hydrophobic spacers, or linker segments that participate in subsequent deprotection and coupling steps, aligning with standard peptide chemistry compatibility.
3. Side-Chain Functionalization
L-2-Aminoundecanoic acid can serve as a feedstock for side-chain functionalization strategies that exploit the long methylene segment as a handle for hydrophobic tethering and subsequent derivatization. The amino acid backbone allows conversion into N-protected intermediates, after which the carboxyl group can be esterified or amidated to tune reactivity and handleability for downstream transformations. Functional group interconversions can be applied to generate derivatives such as alkyl amides, thioester-like intermediates, or further substituted hydrophobic linkers, while stereochemical integrity at the L-center is retained through protection and activation steps. The resulting functionalized amino acid derivatives can then be used to prepare peptide conjugation reagents, hydrophobic anchors for biomolecule modification, or processable intermediates for specialty chemical production.
4. Chemical Biology Conjugation
L-2-Aminoundecanoic acid is applicable to chemical biology and biomolecule modification workflows where a hydrophobic amino acid segment can modulate solubility, binding, and conjugate architecture. The presence of both an amino group and a carboxylic acid enables formation of stable amide linkages to biomolecule-reactive scaffolds after appropriate protection and activation, supporting design of hydrophobic linkers for probes and affinity reagents. The L-amino acid stereocenter can be preserved during conjugation to maintain defined stereochemical features that may influence recognition by chiral receptors or enzyme-active sites in assay formats. Downstream derivatives prepared from this building block can be incorporated into conjugation constructs for labeling strategies, enabling controlled synthesis of amphiphilic conjugates and peptide-based chemical tools.
5. Industrial Biocatalysis And Process Chemistry
L-2-Aminoundecanoic acid can be employed in process chemistry and industrial intermediate preparation where chiral amino acid building blocks are required for manufacturing of long-chain amide and peptide-like materials. The amino acid's bifunctional structure supports conversion into activated intermediates or protected forms that can be fed into coupling operations under scalable conditions, including routes that rely on standard carbodiimide-type activation or esterification/amide formation strategies. The extended aliphatic chain can be leveraged to produce hydrophobic segments used in specialty chemical production, such as surfactant-like linkers, polymerizable monomers, or long-chain amide derivatives. The compound's L-stereochemistry makes it suitable for stereodefined syntheses where downstream chiral integrity is required for consistent material properties or for reproducible intermediate performance in multi-step industrial manufacturing.
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