N-α,N-γ-di-Boc-D-2,4-diaminobutyric acid dicyclohexylamine salt is a protected, D-configured amino acid derivative featuring a 2,4-diaminobutyric acid backbone bearing two tert-butoxycarbonyl (Boc) protecting groups on the α-amino and γ-amino nitrogens. The molecule contains a free carboxyl functional group while the remaining amine functionality is masked as Boc carbamates, and the dicyclohexylamine component forms an acid-base salt with the carboxyl group, affecting solubility and handling during synthesis. It is used as a stepwise building block in peptide and peptidomimetic synthesis where orthogonal protection and controlled deprotection of diamino functionalities can be leveraged for constructing defined substitution patterns and for preparing more complex amino acid and peptide derivatives.
CAT No: CP05309
N-α,N-γ-di-Boc-D-2,4-diaminobutyric acid dicyclohexylamine salt is a protected D-2,4-diaminobutyric acid derivative in which the α-amino and γ-amino functionalities are masked as Boc carbamates, while the carboxyl group remains available for controlled activation in peptide coupling chemistry. The D stereochemistry fixes the chiral center at the amino acid backbone, enabling stereodefined incorporation into oligopeptides and peptidomimetic scaffolds. The dicyclohexylamine salt form provides a practical, isolable counterion environment that can influence handling, crystallinity, and downstream deprotection or coupling workflows. Boc-protected amines enable orthogonal deprotection strategies, and the diamino side-chain architecture supports sequential functional group transformations after selective Boc removal.
1. Peptide Synthesis
N-α,N-γ-di-Boc-D-2,4-diaminobutyric acid dicyclohexylamine salt supports peptide building block preparation where both α- and γ-amino sites are protected as Boc carbamates, reducing undesired side reactions during stepwise assembly. The amino acid backbone provides a defined stereocenter for stereospecific peptide bond formation, while the protected diamine side chain can be unmasked at a chosen stage to introduce branching, additional amide formation, or side-chain elaboration. Boc groups are compatible with standard peptide coupling cycles and can be removed to generate reactive amines for subsequent coupling or derivatization. Downstream, the resulting peptides and peptide-like intermediates can be used to construct constrained or cationic motifs relevant to peptide science and synthetic methodology development.
2. Side-Chain Functionalization
N-α,N-γ-di-Boc-D-2,4-diaminobutyric acid dicyclohexylamine salt is suitable for side-chain functionalization workflows that exploit its diamino architecture and orthogonal Boc deprotection logic. The γ-amino Boc protecting group can be selectively removed under controlled conditions to reveal a primary amine for conjugation handles such as acylation, sulfonylation, or formation of urea and carbamate linkages. The remaining α-Boc can be managed to control whether the compound participates as a coupling partner or serves as an intermediate for installing functional groups onto peptide backbones. The dicyclohexylamine salt form can also aid reproducible handling in fine chemical synthesis where consistent salt formation supports downstream processing and intermediate isolation.
3. Chemical Biology Probes
N-α,N-γ-di-Boc-D-2,4-diaminobutyric acid dicyclohexylamine salt can be applied in chemical biology probe construction where a stereodefined, diamino-containing residue is incorporated into peptide-based recognition elements. Boc-protected amines limit premature labeling during synthesis, while post-synthetic deprotection enables attachment of fluorophores, affinity tags, or clickable groups through the exposed primary amine. The D-configuration can be used to tune conformational preferences and reduce proteolytic susceptibility when incorporated into peptide analogs used for binding studies or target engagement assays. The resulting labeled or functionalized peptide constructs serve as research intermediates for mapping molecular interactions and generating structure-defined reagents for biochemical investigations.
4. Peptidomimetics And SAR Studies
N-α,N-γ-di-Boc-D-2,4-diaminobutyric acid dicyclohexylamine salt is relevant to peptidomimetic construction and structure-activity relationship studies that require a chiral, diamino scaffold with controlled functional group density. Boc protection provides a stable platform for assembling analog libraries where the side-chain amines can later be converted into amide, urea, or heteroatom-containing motifs that modulate hydrogen bonding and charge distribution. The fixed D stereochemistry supports consistent SAR comparisons across analog series by maintaining stereochemical identity at the residue level. Downstream, the compound can feed into fragment-based or scaffold-hopping synthetic routes that generate stereodefined peptidomimetic intermediates for medicinal chemistry optimization.
5. Pharmaceutical Intermediate Preparation
N-α,N-γ-di-Boc-D-2,4-diaminobutyric acid dicyclohexylamine salt can be employed as a process chemistry intermediate for manufacturing routes that require protected amino acid derivatives with predictable deprotection behavior. The Boc-protected α- and γ-amines minimize cross-reactivity during activation of the carboxyl group and during coupling to form defined amide linkages in larger synthetic sequences. The salt form can support isolation and handling in industrial fine chemical production, where reproducible solid-state properties and controlled reactivity are important for scale-up. Downstream use includes preparation of stereodefined peptide fragments, protected building blocks, and amine-functionalized intermediates that can be further processed into drug-like molecules or advanced synthetic intermediates.
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