N-α-Fmoc-N-ε-allyoxycarbonyl-D-lysine is a protected amino acid derivative of D-lysine featuring an α-amino group masked as an Fmoc carbamate and an ε-amino side chain masked as an allyoxycarbonyl (Alloc) carbamate. The molecule contains a free carboxyl functional group and bears two orthogonal protecting groups with distinct removal conditions, while the D-lysine stereochemistry is specified by the D configuration in the name and the aliphatic side chain retains the characteristic lysine chain length. In peptide synthesis workflows, this orthogonally protected building block is used to control chemoselective deprotection and coupling at the α- and ε-amino positions, supporting the stepwise preparation of lysine-containing peptides and related amino acid conjugates.
CAT No: CP01434
CAS No:214750-75-1
Synonyms/Alias:Fmoc-D-Lys(Alloc)-OH;214750-75-1;N-Fmoc-N'-allyloxycarbonyl-D-lysine;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-(((allyloxy)carbonyl)amino)hexanoicacid;AmbotzFAA1329;SCHEMBL178771;N|A-Alloc-N|A-Fmoc-D-lysine;N|A-Fmoc-N|A-Alloc-D-lysine;CTK1A1485;MolPort-008-267-644;CF-012;ZINC15722156;AKOS024258693;AJ-67846;AK151396;FT-0643977
N-α-Fmoc-N-ε-allyoxycarbonyl-D-lysine is a D-lysine derivative bearing an Fmoc-protected α-amino group and an allyoxycarbonyl (Alloc) protected ε-amino group, providing orthogonal amine protection for stepwise peptide assembly. The lysine backbone presents a stereogenic center at the α-carbon, while the side chain terminates in a protected primary amine that can be selectively deprotected to enable ε-functionalization. The Fmoc group is base-labile and the Alloc group is typically removable under conditions compatible with peptide intermediates, allowing controlled exposure of either the α- or ε-nucleophile. The molecule also contains the carboxylate functionality of a protected amino acid building block, supporting standard peptide coupling chemistry and downstream conversion into mono- or di-functional lysine derivatives for synthetic and biochemical workflows.
1. Orthogonal Peptide Coupling
N-α-Fmoc-N-ε-allyoxycarbonyl-D-lysine is used in peptide synthesis workflows that require orthogonal protection of lysine, where the Fmoc group governs α-amide formation and the Alloc group suppresses ε-amine reactivity during early coupling steps. The D-lysine stereochemistry fixes the spatial arrangement of the side chain, which can influence conformational preferences in lysine-containing sequences and peptidomimetic scaffolds. Orthogonal deprotection enables sequential access to the α- and ε-nitrogen atoms, supporting selective incorporation of lysine at defined positions and controlled generation of ε-amide or ε-linker functionalities. Downstream, the protected lysine building block can be converted into mono-ε-functionalized peptides, branched lysine derivatives, or site-selectively modified analogs used in structure-activity relationship studies and synthetic methodology development.
2. Side-Chain Functionalization
N-α-Fmoc-N-ε-allyoxycarbonyl-D-lysine is applied to side-chain functionalization strategies for generating ε-amino-reactive intermediates without perturbing the α-protecting group during derivatization. The Alloc-protected ε-amine can be selectively unmasked to furnish a nucleophilic ε-nitrogen for coupling to activated acids, carbonyl electrophiles, or activated linkers used in affinity handles and solubilizing tags. The presence of the Fmoc group maintains compatibility with solid-phase peptide synthesis conditions while allowing controlled timing of ε-modification to produce peptides with defined charge distribution and spacing. Resulting ε-functionalized lysine derivatives can serve as intermediates for bioconjugation chemistry, molecular probes, and synthetic organic chemistry routes that require site-specific attachment of functional groups.
3. Chemical Biology Labeling
N-α-Fmoc-N-ε-allyoxycarbonyl-D-lysine supports chemical biology and biomolecule labeling approaches where lysine residues are used as conjugation points for attaching dyes, affinity ligands, or reporter groups. The protected amine architecture enables preparation of peptide building blocks that can be assembled into defined sequences before selective ε-deprotection and conjugation, improving control over labeling position and reducing off-target modification. D-lysine incorporation can be used to tune backbone stereochemistry and proteolytic stability of labeled peptide constructs used as research tools for receptor binding studies, cellular uptake assays, and mapping of molecular interactions. Downstream derivatives include fluorescently labeled peptides, affinity-tagged probes, and standardized conjugation intermediates for analytical research and molecular recognition studies.
4. Peptidomimetic And SAR Studies
N-α-Fmoc-N-ε-allyoxycarbonyl-D-lysine is suitable for peptidomimetic construction and structure-activity relationship (SAR) exploration where controlled lysine side-chain chemistry is required to vary electrostatics, linker length, and functional group identity. The orthogonally protected α- and ε-amines allow synthesis of analog libraries with consistent backbone architecture while enabling systematic modification at the ε-position after sequence assembly. The fixed D-configuration at the α-carbon provides a stereochemically defined lysine analog that can be incorporated into non-natural peptide scaffolds to probe structure-function relationships. Generated lysine-containing analogs can be used as comparative substrates in biochemical assays, as scaffold components in medicinal chemistry programs, and as defined standards for analytical characterization of SAR series.
5. Pharmaceutical Intermediate Preparation
N-α-Fmoc-N-ε-allyoxycarbonyl-D-lysine is employed in pharmaceutical intermediate preparation for manufacturing-grade peptide and peptide-like intermediates where reproducible protection/deprotection logic is required for process control. The Fmoc/Alloc orthogonality supports stepwise amine exposure, enabling selective coupling at the α-position and later controlled ε-functionalization during downstream processing of lysine-containing sequences. The protected amino acid form is compatible with established peptide coupling chemistries used in fine chemical synthesis, supporting scalable assembly of protected peptide fragments and defined building blocks for further derivatization. Resulting intermediates can feed into downstream synthesis of labeled or functionalized peptide reagents used in applied product development, including chemical manufacturing of research materials and specialized peptide-based components.
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