N-α-Boc-N-γ-allyloxycarbonyl-D-2,4 diaminobutyric acid dicyclohexylamine salt is a protected, non-proteinogenic amino acid derivative featuring a 2,4-diaminobutyric acid backbone with both α-amino and γ-amino functionalities masked by carbamate protecting groups. The molecule contains a Boc-protected α-amino group and an allyloxycarbonyl (Alloc) protected γ-amino group, while the carboxyl group is present as part of the amino acid salt form with dicyclohexylamine; the "D" designation indicates the stereochemical configuration at the chiral center as specified by the product name. In peptide and amino acid synthesis workflows, the orthogonal Boc/Alloc protection pattern supports chemoselective deprotection and stepwise incorporation of a diamino side chain for preparing structured peptide analogues, conjugation handles, and analytical standards that require controlled presentation of amine functionality.
CAT No: CP05307
N-α-Boc-N-γ-allyloxycarbonyl-D-2,4 diaminobutyric acid dicyclohexylamine salt is a chiral, protected diamino acid derivative in which the D-2,4-diaminobutyric acid scaffold is masked by an N-α Boc group and an N-γ allyloxycarbonyl (Alloc) protecting group. The molecule contains two stereochemically defined amino functionalities along the side chain, enabling orthogonal protection logic for sequential functionalization while maintaining compatibility with peptide coupling conditions. The dicyclohexylamine salt form improves handling and can influence crystallization behavior for synthetic workflows, while the Boc and Alloc groups provide controlled deprotection windows for downstream assembly. The presence of an allyl carbonate protecting group and a tert-butyl carbamate also supports predictable reactivity under standard orthogonal deprotection strategies used in peptide and amino acid chemistry, making the compound suitable for constructing protected amino acid building blocks and derivatized intermediates.
1. Protected Amino Acid Synthesis
N-α-Boc-N-γ-allyloxycarbonyl-D-2,4 diaminobutyric acid dicyclohexylamine salt serves as a protected amino acid intermediate for orthogonally protected diamino acid synthesis, where the N-α Boc and N-γ Alloc groups allow selective deprotection and subsequent derivatization. The D-configuration fixes the stereochemical outcome of side-chain functionalization steps, while the two amino sites enable formation of distinct amide or carbamate linkages after controlled unmasking. The Alloc group can be removed under conditions compatible with Boc retention, enabling stepwise conversion into peptide-ready or scaffold-ready forms. The resulting protected diamino acid derivatives can be carried into fine chemical synthesis routes requiring controlled introduction of two nitrogen functionalities.
2. Peptide Synthesis
N-α-Boc-N-γ-allyloxycarbonyl-D-2,4 diaminobutyric acid dicyclohexylamine salt is suitable for peptide building block preparation in peptide coupling workflows that require orthogonal protection of diamino acid side chains. The N-α Boc group supports conventional N-acylation chemistry after deprotection, while the N-γ Alloc group can be unmasked later to generate a reactive amine for intramolecular cyclization, additional coupling, or side-chain functionalization. The amino acid backbone and protected amines can be incorporated into linear peptides, branched peptides, or protected peptide fragments where controlled access to side-chain nitrogen is required to tune charge and hydrogen-bonding patterns. The dicyclohexylamine salt form can support reproducible handling during solid-phase or solution-phase peptide assembly, supporting downstream generation of peptide analogs with defined stereochemistry.
3. Chemical Biology Conjugation
N-α-Boc-N-γ-allyloxycarbonyl-D-2,4 diaminobutyric acid dicyclohexylamine salt can be applied in chemical biology workflows that require controlled introduction of a diamino acid motif for conjugation chemistry. The orthogonally protected amines enable sequential installation of linkers, handles, or recognition elements, where unmasking of the N-γ Alloc-derived amine can generate a site for coupling to electrophiles or activated acids without disturbing the N-α functionality. The D-2,4-diaminobutyric acid framework can contribute defined basicity and spacing between nitrogen atoms, which can influence conjugate solubility and binding geometry in labeling reagents or molecular probes. The protected intermediate nature of the compound supports iterative build-up of bioconjugation-ready derivatives used in biomolecule modification and targeted chemical probe construction.
4. Peptidomimetics And SAR Studies
N-α-Boc-N-γ-allyloxycarbonyl-D-2,4 diaminobutyric acid dicyclohexylamine salt supports peptidomimetic construction for structure-activity relationship studies where diamino acid spacing and stereochemistry are key determinants of binding and stability. The protected N-α and N-γ nitrogens allow controlled transformation into amide, urea, or carbamate functionalities that can modulate conformational preferences and hydrogen-bonding networks in peptide analogs. Alloc deprotection and subsequent functional group installation can be used to generate side-chain substituted variants, including tethered groups for receptor engagement or resistance to proteolysis. The compound's compatibility with standard peptide chemistry logic enables systematic generation of closely related analog series for SAR-focused molecular design and assay material preparation.
5. Pharmaceutical Intermediate Preparation
N-α-Boc-N-γ-allyloxycarbonyl-D-2,4 diaminobutyric acid dicyclohexylamine salt is applicable to pharmaceutical intermediate preparation where orthogonally protected diamino acid building blocks are required for controlled synthesis of nitrogen-rich fragments. The Boc and Alloc protecting groups provide a practical strategy for managing chemoselectivity during stepwise assembly, enabling formation of protected amide bonds and later conversion of the side-chain amine into drug-like functionalities such as substituted ureas or amide-linked substituents. The D-stereocenter supports stereochemically defined intermediate formation, which is often required for downstream medicinal chemistry campaigns and process development. The salt form can be leveraged in industrial fine chemical manufacturing to facilitate isolation and handling of the chiral protected amino acid intermediate prior to conversion into final synthetic intermediates.
6. Process Chemistry And Fine Chemical Synthesis
N-α-Boc-N-γ-allyloxycarbonyl-D-2,4 diaminobutyric acid dicyclohexylamine salt can be employed in process chemistry and fine chemical synthesis as a chiral, orthogonally protected amino acid intermediate for scalable route design. The presence of two protected amino sites with distinct deprotection behavior supports stepwise manufacturing sequences that minimize cross-reactivity and allow predictable functional group timing. The allyloxycarbonyl group provides an orthogonal handle for controlled side-chain unmasking, while the Boc group supports stability through coupling and intermediate isolation steps. The compound's amino acid backbone and protected nitrogen functionality make it suitable for producing downstream derivatives used in industrial synthesis of peptidomimetic scaffolds, specialty intermediates, and nitrogen-rich functional building blocks for applied chemical manufacturing.
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