Fmoc-L-homoleucine is an Fmoc-protected, naturally occurring amino acid derivative featuring an L-configured α-amino acid backbone with a branched aliphatic side chain characteristic of homoleucine. The molecule contains a free carboxylic acid functionality alongside the α-amino group masked by the fluorenylmethoxycarbonyl (Fmoc) protecting group, which controls chemoselectivity during stepwise peptide assembly. In peptide chemistry and solid-phase peptide synthesis, it is employed as a protected building block to introduce the homoleucine side chain into peptide sequences while the Fmoc group is removed under base-mediated conditions to regenerate the reactive amine for subsequent coupling.
CAT No: CP06505
CAS No:193954-27-7
Synonyms/Alias:Fmoc-L-beta-homoisoleucine;193954-27-7;Fmoc-beta-Homoile-OH;Fmoc-beta-Hoile-OH;(3R,4S)-3-(Fmoc-amino)-4-methylhexanoicacid;Fmoc--Homoile-OH;Fmoc-|A-Homoile-OH;Fmoc-L-?-Homoisoleucine;Fmoc-L-|A-homoisoleucine;SCHEMBL119195;03671_FLUKA;MolPort-000-162-473;ZINC2386816;CF-327;AKOS016003206;AJ-35384;AK-89155;AM803448;KB-52093;TR-009013;FT-0653047;ST24047276;V1050
Fmoc-L-homoleucine is an Fmoc-protected L-homoleucine amino acid building block featuring a chiral, aliphatic side chain with an extended isobutyl-like framework and an N-(9H-fluoren-9-ylmethoxycarbonyl) protecting group. The molecule contains a protected amine (carbamate) and a free carboxylic acid, enabling controlled peptide coupling while maintaining stereochemical integrity at the α-carbon. The hydrophobic side chain supports incorporation into peptide sequences and peptidomimetic scaffolds where conformational bias and lipophilicity influence molecular recognition. The Fmoc group is compatible with standard base-mediated deprotection strategies, making the compound suitable for iterative solid-phase or solution-phase assembly of protected amino acid derivatives and downstream synthetic intermediates.
1. Peptide Synthesis
Fmoc-L-homoleucine is used in peptide synthesis workflows where Fmoc chemistry enables stepwise N-terminal protection and deprotection during chain elongation. The free carboxylic acid and Fmoc-protected amine provide the functional pairing needed for peptide coupling while the L-configuration at the α-stereocenter is retained through standard coupling conditions. The homoleucine side chain contributes hydrophobic character and steric bulk that can affect backbone torsion preferences and side-chain packing in the growing sequence. The resulting homoleucine-containing peptides can be generated for structure-activity relationship studies, scaffold diversification, and peptide analog libraries in both academic and industrial peptide manufacturing settings.
2. Side-Chain Functionalization
Fmoc-L-homoleucine supports side-chain functionalization strategies that start from a protected amino acid intermediate and proceed through selective modification of the aliphatic side chain. The Fmoc carbamate allows orthogonal handling of the amino group while the carboxylic acid can be converted to activated esters or retained for later coupling steps. The extended hydrophobic side chain can serve as a handle for introducing additional substituents that tune lipophilicity, solubility, and membrane affinity in peptidomimetic design. Downstream derivatives formed from this intermediate can be used to generate analog series for chemical biology research and to prepare non-natural amino acid variants for fine chemical synthesis.
3. Chiral Building Block Development
Fmoc-L-homoleucine is applied as a chiral amino acid intermediate in stereocontrolled synthesis of non-natural peptide-like structures and chiral fragments. The single defined stereocenter at the α-carbon, combined with the stable Fmoc protecting group, enables the compound to function as a reliable input for asymmetric or stereospecific assembly routes where configuration must be preserved. The protected amine and carboxyl group allow transformation into coupling-ready derivatives, including activated carboxylic acid forms, while maintaining the stereochemical outcome of the building block. The resulting chiral intermediates can be incorporated into medicinal chemistry and materials-oriented molecular design programs requiring consistent stereodefined amino acid units.
4. Peptidomimetics And SAR
Fmoc-L-homoleucine is suitable for peptidomimetic construction where hydrophobic side-chain topology is used to modulate conformational behavior and binding interfaces in SAR studies. The homoleucine residue can be incorporated into peptide analogs to probe the impact of increased side-chain length and bulk relative to leucine, while the Fmoc group supports systematic synthesis of analog panels. The protected amino acid format enables rapid generation of sequence variants through iterative coupling and controlled deprotection, supporting structure-activity relationship workflows. The homoleucine-containing scaffolds produced from this intermediate can be further diversified into chemically stabilized analogs used in applied research and industrial fine chemical programs focused on library synthesis.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-L-homoleucine is relevant to pharmaceutical manufacturing and process chemistry contexts as a protected amino acid intermediate compatible with scalable peptide building strategies. The Fmoc carbamate and free carboxylic acid define a practical protection pattern for manufacturing routes that require predictable coupling behavior and controlled deprotection steps during intermediate isolation and purification. The hydrophobic homoleucine side chain can be incorporated into drug-like peptide fragments and peptidic intermediates where side-chain composition influences solubility and solid-state properties. The compound can therefore serve as a reproducible input for producing protected amino acid derivatives and peptide intermediates used in specialty chemical production and industrial-scale synthesis planning.
6. Chemical Biology Labeling
Fmoc-L-homoleucine can be employed in chemical biology research to build labeled peptides and functional conjugation-ready fragments where controlled N-terminal protection is required. The Fmoc group supports assembly of peptide sequences that can later be selectively deprotected to expose reactive termini for subsequent conjugation chemistry, while the homoleucine side chain contributes to hydrophobic interactions that may influence labeling reagent localization or binding behavior. The free carboxylic acid enables formation of activated derivatives for coupling to probes, linkers, or scaffold molecules after peptide assembly. The resulting labeled or derivatized peptide constructs can be used in biomolecule interaction studies and analytical research workflows that rely on reproducible amino acid composition and stereodefined building blocks.
1. Cell-based adhesion assays for isolation of snake venom’s integrin antagonists
2. An Open-label, Single-center, Safety and Efficacy Study of Eyelash Polygrowth Factor Serum
3. Myotropic activity of allatostatins in tenebrionid beetles
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