Dde-L-Dap(Aloc)-OH is a protected, non-proteinogenic amino acid derivative based on L-2,3-diaminopropanoic acid (L-Dap) in which the side-chain amino group is substituted with an Alloc (allyloxycarbonyl) protecting group and the α-amino functionality is masked as a Dde (1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl) carbamoyl protecting group. The molecule bears a free carboxylic acid (-COOH) and retains stereochemistry at the α-carbon as indicated by the "L" designation, while the two protected amines are prevented from participating in unprotected amide-forming reactions during stepwise assembly. Dde-L-Dap(Aloc)-OH is used as a building block for peptide synthesis and related amino acid coupling workflows where orthogonal deprotection and controlled chemoselectivity are required to introduce the diamino side chain at a defined position.
CAT No: CP25259
CAS No:1263045-89-1
Chemical Name:N-alpha-(4-4-Dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-beta-allyloxycarbonyl-L-2,3-diaminopropionic acid
Dde-L-Dap(Aloc)-OH is a chiral, side-chain protected amino acid derivative based on L-2,3-diaminopropanoic acid (L-Dap) bearing two orthogonally removable protecting groups on the side-chain nitrogens: a Dde (1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethylidene) group and an Aloc (allyloxycarbonyl) group. The molecule presents a free carboxylic acid (-CO2H) for C-terminal activation and peptide coupling, while the backbone stereocenter is configured as L, enabling stereochemically defined incorporation into peptide sequences. Orthogonal deprotection behavior allows selective exposure of one or both side-chain amines under controlled conditions, supporting iterative peptide synthesis and stepwise functionalization. The presence of protected amines and a carboxylic acid makes the compound compatible with protected amino acid chemistry, including activation to acylating intermediates and subsequent downstream transformations into guanidinium-like or amide/urea/amine-derived motifs.
1. Peptide Synthesis
Dde-L-Dap(Aloc)-OH supports peptide building-block workflows where protected side-chain nitrogens are required to control chemoselectivity during chain assembly. The free carboxylic acid enables C-terminal activation for amide bond formation, while the Dde and Aloc groups help suppress undesired side reactions from the diamine side chain during coupling cycles. Orthogonal deprotection enables sequential unmasking of side-chain amino functionality for on-resin or solution-phase post-coupling modifications, including formation of internal linkages or attachment of functional substituents. The stereodefined L-Dap backbone further supports the construction of peptides and peptidomimetics that rely on precise spatial positioning of diamine-derived pharmacophores.
2. Side-Chain Functionalization
Dde-L-Dap(Aloc)-OH functions as a platform for side-chain functionalization strategies targeting diamine-derived reactivity without cross-reactivity between the two nitrogen sites. The protected amines allow controlled conversion into substituted amide, urea, carbamate, sulfonamide, or alkylated amine derivatives after selective deprotection, enabling targeted modulation of charge density, hydrogen-bonding patterns, and solubility. The carboxylic acid permits conversion into activated derivatives or coupling partners that can be carried into subsequent synthetic steps while maintaining orthogonal protection logic. Stepwise exposure of amine sites supports the generation of defined mono- or di-functionalized amino acid analogs used in structure-activity relationship studies and biochemical probe construction.
3. Chemical Biology Probes
Dde-L-Dap(Aloc)-OH is suitable for chemical biology applications that require incorporation of a protected diamino acid residue into peptide-based probes and affinity ligands. The orthogonally protected side-chain nitrogens can be unmasked to introduce handles for conjugation such as linkers, fluorescent tags, affinity moieties, or reactive electrophiles used for labeling workflows. The L-configured amino acid core enables predictable placement of the diamine motif within peptide scaffolds, supporting consistent molecular recognition behavior in experimental binding assays. Downstream derivatization can yield labeled or functionalized peptide constructs that serve as reagents for biomolecule interaction studies, receptor mapping, and pathway interrogation using defined amino acid chemistry.
4. Peptidomimetics And SAR
Dde-L-Dap(Aloc)-OH can be employed in peptidomimetic construction and SAR-oriented library synthesis where diamine-containing motifs are used to tune potency-related physicochemical properties. The Dde and Aloc protecting groups provide a synthetic handle for generating specific substitution patterns on the side chain while preventing premature reactions during scaffold assembly. The free carboxylic acid supports incorporation into larger frameworks through peptide coupling chemistry or conversion to activated intermediates for scaffold diversification. Defined stereochemistry and controlled side-chain substitution enable systematic variation of charge distribution and hydrogen-bonding geometry, supporting SAR studies focused on amino acid derivative structure-function relationships.
5. Pharmaceutical Intermediate Preparation
Dde-L-Dap(Aloc)-OH is applicable to pharmaceutical intermediate preparation where protected amino acid derivatives are required for controlled synthesis of amide-rich intermediates and nitrogen-functionalized fragments. The carboxylic acid group facilitates conversion into acylating species for incorporation into larger synthetic sequences, while the orthogonal Dde/Aloc protection strategy supports stepwise introduction of side-chain functionality under manufacturing-relevant chemoselectivity constraints. The diamine side chain, when protected, reduces risk of uncontrolled cross-linking or overreaction during upstream steps, improving compatibility with iterative coupling and purification operations. The resulting derivatives can serve as intermediates toward peptide-like building blocks, nitrogen-rich heteroatom-containing structures, and processable fine chemicals derived from amino acid chemistry.
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