Dde-L-Lys(Aloc)-OH*DCHA is a protected amino acid derivative based on L-lysine, bearing a side-chain ε-amino group protected as an allyloxycarbonyl (Aloc) carbamate and a carboxyl group present as a free acid. The name indicates the Dde (1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl) protection on the α-amino functionality and an Aloc-protected lysine side chain, with stereochemistry specified as L for the lysine backbone. This molecule is employed as a building block for stepwise peptide synthesis and related chemical biology workflows where orthogonal removal of the Dde and Aloc protecting groups supports controlled exposure of amino functionalities for sequential coupling and for preparation of lysine-containing peptide derivatives.
CAT No: CP25683
CAS No:264230-73-1
Synonyms/Alias:N-alpha-Dde-N-epsilon-Alloc-L-lysine*DCHA;Dde-Lys(Aloc)*DCHA
Chemical Name:N-alpha-(4-4-Dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-epsilon-allyloxycarbonyl-L-lysine dicyclohexylamine
Dde-L-Lys(Aloc)-OH*DCHA is a chiral lysine-based protected amino acid derivative featuring the L-lysine stereocenter at the α-carbon and a side-chain ε-amino group masked by orthogonal protecting groups. The Dde group and the Aloc (alloc) group are installed to enable selective deprotection control during peptide assembly, while the carboxylic acid remains available for C-terminal activation and coupling. The presence of DCHA indicates a defined counterion/complexing form that can influence handling, crystallinity, and downstream salt formation behavior for synthetic workflows. The compound's protected amine functionality supports standard peptide coupling chemistry after appropriate deprotection steps, while the orthogonal protecting-group set supports iterative N- and side-chain functionalization with stereochemical fidelity.
1. Orthogonal Peptide Coupling
Dde-L-Lys(Aloc)-OH*DCHA is applied in peptide synthesis workflows requiring orthogonal protection of lysine to control sequential amide bond formation. The protected ε-amino side chain and the α-carboxylic acid provide a clear coupling handle once the relevant protecting group is removed under conditions compatible with the remaining group. The Dde/Aloc pair enables stepwise generation of a single free amine for targeted coupling, supporting lysine-containing peptide building block preparation and controlled branching in peptide sequences. The resulting protected lysine intermediate can be incorporated into longer chains for the construction of peptides, peptide fragments, and protected peptide analogs used in biochemical research and method development. The lysine stereochemistry and orthogonal deprotection logic align with standard peptide chemistry strategies used for reproducible synthetic assembly.
2. Side-Chain Functionalization
Dde-L-Lys(Aloc)-OH*DCHA supports side-chain functionalization strategies in chemical biology and synthetic organic chemistry where ε-amino reactivity must be introduced at a defined stage. The orthogonally protected lysine side chain allows selective unveiling of the nucleophilic amine, enabling subsequent derivatization such as acylation, sulfonylation, carbamate formation, or conjugation precursor generation. The Dde and Aloc protecting groups help maintain the integrity of other functional sites during intermediate transformations, reducing undesired cross-reactivity during multi-step syntheses. The protected lysine scaffold can therefore serve as a controlled platform for installing functional moieties that later participate in peptide conjugation or biomolecule modification. Downstream products include functionalized amino acid derivatives and peptide analogs bearing lysine-derived handles for further chemical elaboration.
3. Bioconjugation Chemistry
Dde-L-Lys(Aloc)-OH*DCHA is suitable for bioconjugation chemistry programs that require lysine-based attachment points with controlled protection and deprotection sequencing. The ε-amino group, once selectively liberated from the Dde/Aloc protection scheme, can be used to generate reactive intermediates for coupling to carriers, linkers, or targeting ligands under conditions that preserve peptide backbone integrity. The carboxylic acid functionality enables incorporation into peptide-based conjugates through peptide coupling chemistry, while the orthogonal protecting groups support selective functional group exposure. The compound can be employed to prepare conjugation-ready peptide fragments and defined lysine-containing constructs used in chemical biology workflows such as probe assembly and labeling reagent synthesis. The stereochemically defined lysine core supports consistent molecular recognition behavior in downstream conjugate formation.
4. Process Chemistry Intermediate
Dde-L-Lys(Aloc)-OH*DCHA is relevant to process chemistry intermediate preparation where orthogonally protected amino acids are manufactured for scalable peptide building block supply. The presence of stable protecting-group motifs on the lysine side chain supports controlled deprotection steps that can be integrated into manufacturing routes for protected amino acid synthesis and peptide-grade intermediate generation. The carboxylic acid and protected amine functionality align with common industrial coupling and salt-management practices used to streamline downstream transformations. The DCHA form can be leveraged for reproducible handling characteristics in synthetic operations that depend on solid-state behavior and consistent material transfer. The compound's design as a chiral lysine derivative with orthogonal N-protection makes it compatible with industrial fine chemical synthesis of peptide intermediates and protected amino acid building blocks.
5. Analytical Reference Standards
Dde-L-Lys(Aloc)-OH*DCHA can be used in analytical research for method development and characterization of protected lysine-containing intermediates and peptide fragments. The defined stereochemistry and the presence of Dde and Aloc protecting groups create characteristic chromatographic and spectroscopic signatures that support identification and purity assessment of lysine-derived building blocks. The carboxylic acid and protected amine enable formation of defined derivatives during analytical workflows, supporting calibration and structural confirmation for peptide coupling studies. The DCHA-associated form can also provide a consistent reference material for evaluating salt-dependent behavior in sample preparation and analytical measurements. The compound thus functions as a chemically defined reference for monitoring orthogonal deprotection progression and for verifying structural integrity of peptide synthesis intermediates.
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