D-homoleucine is a non-proteinogenic branched-chain amino acid featuring an extended aliphatic side chain relative to leucine, with the amino acid backbone bearing a primary amino group and a carboxyl group. The molecule is classified as a D stereoisomer as indicated by its name and presents a hydrophobic, alkyl side chain that can participate in peptide bond formation as a substrate analog in synthetic sequences. D-homoleucine is used in peptide synthesis and structure-activity or conformational studies where variation of side-chain length and hydrophobic character is used to probe effects on peptide properties and analytical standards.
CAT No: CP06502
D-homoleucine is a D-configured, non-proteinogenic amino acid homolog of leucine with an extended side chain that increases hydrophobic surface area and conformational flexibility. The molecule contains a stereogenic alpha carbon bearing a free amino group and a carboxylic acid (or, depending on supplied form, readily interconvertible protected/activated equivalents), enabling standard amino acid coupling chemistry. The aliphatic side chain can participate in hydrophobic interactions and can be further functionalized through oxidation, halogenation, or side-chain elaboration to generate additional reactive handles. As a chiral amino acid building block, D-homoleucine serves as a stereochemically defined intermediate for peptide construction, chiral synthesis, and downstream derivatization where D-amino acid incorporation modulates peptide stability and recognition.
1. Peptide Synthesis
D-homoleucine is applied in peptide building and fragment assembly where the D-amino acid stereochemistry supports incorporation into peptide sequences using standard amide-forming coupling strategies. The amino acid backbone provides an alpha-amino and alpha-carboxyl functionality that can be converted into protected amino acid derivatives for iterative N- and C-terminal peptide synthesis. Side-chain length relative to leucine can influence local backbone conformations and hydrophobic packing in peptide scaffolds, making D-homoleucine suitable for constructing stereodefined analogs for sequence optimization. Downstream peptide products can be used as research-grade materials for studying D-residue effects on folding, proteolytic resistance, and binding-site complementarity in peptide science.
2. Chiral Building Blocks
D-homoleucine is used as a chiral amino acid intermediate for stereoselective synthesis of enantiopure derivatives and process chemistry intermediates. The defined D-configuration at the alpha carbon enables retention of stereochemistry through activation of the carboxyl group and subsequent derivatization of the amino functionality using protecting-group strategies. The extended aliphatic side chain supports conversion into functionalized chiral intermediates, including side-chain-modified amino acids, lactam precursors, or further elaborated chiral fragments. The resulting stereochemically controlled intermediates can feed into fine chemical synthesis and chiral library generation for medicinal chemistry and materials-related route development.
3. Side-Chain Functionalization
D-homoleucine is applied in amino acid derivatization workflows targeting side-chain modification of an aliphatic, hydrophobic residue. The hydrocarbon-rich side chain can be transformed into chemically distinct handles through controlled oxidation to introduce hydroxyl or carbonyl functionalities, or through halogenation and subsequent substitution to install nucleophilic or electrophilic groups. The amino acid core can be protected to avoid undesired reactivity during side-chain transformations, then deprotected or coupled after functional group installation. The resulting functionalized D-homoleucine derivatives can be used to generate peptidomimetics, conjugation-ready building blocks, or structure-defined intermediates for studying how hydrophobic chain extension and appended functional groups affect molecular recognition.
4. Chemical Biology Probes
D-homoleucine is utilized in chemical biology research for constructing D-amino acid-containing probes and labeled peptide analogs that probe binding interactions and substrate preferences. The D-stereocenter and hydrophobic side chain can be incorporated into peptide-like scaffolds to tune interaction profiles while maintaining chemical handles for subsequent tagging or reporter installation. Protecting-group strategies on the amino and carboxyl groups enable controlled coupling to biomolecular targets or to affinity reagents without cross-reactivity from the free functional groups. Downstream probe molecules can support biochemical investigations of enzyme tolerance for D-residues, receptor/ligand recognition patterns, and competitive binding in structure-function studies.
5. Pharmaceutical Manufacturing Intermediates
D-homoleucine is used in pharmaceutical intermediate preparation where stereodefined amino acid residues serve as inputs to peptidic or peptidomimetic intermediates. The amino acid's carboxyl functionality and amino functionality can be converted into activated forms suitable for controlled incorporation into larger fragments under manufacturing-relevant conditions. Side-chain length and D-configuration can be leveraged to produce stereochemically consistent intermediates that feed into downstream synthesis of stable peptide analogs, including those designed to resist enzymatic degradation. The compound's role as a chiral, non-proteinogenic building block supports reproducible synthetic routes for fine chemical production and applied peptide chemistry workflows.
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