Boc-D-Dab(Aloc)-OH*DCHA is a protected, non-natural amino acid derivative featuring a D-configured 2,3-diaminobutyric acid (Dab) backbone in which the amino functionality is differentially protected, with the α-amino group masked by a Boc (tert-butoxycarbonyl) carbamate and the side-chain amino protected as an Alloc (allyloxycarbonyl) carbamate. The molecule bears a free carboxylic acid (-COOH) for coupling chemistry and is supplied as a DCHA salt, where DCHA (dicyclohexylamine) associates ionically to the acid/basic sites to form a defined solid-state salt form. In peptide synthesis workflows, the orthogonal Boc/Alloc protection pattern supports stepwise chemoselective deprotection and subsequent amide bond formation, while the Dab side-chain functionality provides a cationic handle that can be incorporated into peptide or peptidomimetic structures for structure-activity and chemical biology studies.
CAT No: CP25791
CAS No:350820-59-6
Synonyms/Alias:350820-59-6;Dicyclohexylamine(R)-2-(((allyloxy)carbonyl)amino)-4-((tert-butoxycarbonyl)amino)butanoate;CTK8C0040;MolPort-023-331-551;ANW-63926;AKOS016003832;AK-61260;KB-251352;RT-021662;Dicyclohexylamine(R)-2-(((allyloxy)carbonyl)amino)-4-((tert-butoxycarbonyl)amino)butyricacid
Chemical Name:N-alpha-t-Butyloxycarbonyl-N-gamma-allyloxycarbonyl-D-2,4-diaminobutyric acid dicyclohexylamine
Boc-D-Dab(Aloc)-OH*DCHA is a protected, stereodefined amino acid building block featuring a Boc-protected amino group and an Aloc (allyloxycarbonyl) protecting group on the side-chain amine of D-Dab (α,α-diaminobutyric acid). The product is supplied as a DCHA salt form, improving handling and weighing for peptide and intermediate synthesis workflows. This combination of orthogonal protecting groups is commonly leveraged to enable selective deprotection steps during complex peptide assembly and to prepare side-chain-functionalized fragments for downstream coupling.
1. Orthogonal Peptide Fragment Assembly
Boc-D-Dab(Aloc)-OH*DCHA is used as a protected residue for constructing peptides that require controlled exposure of the side-chain amine at a specific stage of synthesis. Peptide synthesis teams select this building block when they need the D-Dab side-chain to remain masked during earlier coupling cycles, while still allowing later, selective unmasking for subsequent acylation, alkylation, or attachment of orthogonal functional groups. The Boc group supports standard N-terminal protection strategies, while the Aloc handle enables staged side-chain deprotection without forcing harsh conditions that would compromise other protecting groups in the growing peptide chain.
2. Side-Chain Functionalization Intermediates
Boc-D-Dab(Aloc)-OH*DCHA serves as a practical intermediate for preparing D-Dab-containing peptide fragments and small-molecule scaffolds where the side-chain amine must be introduced in a controlled manner. In medicinal chemistry and peptidomimetic development, researchers often rely on such orthogonally protected amino acids to generate defined amine-bearing intermediates after selective deprotection, followed by coupling to amide-forming partners or attachment of linker units. The DCHA salt form is frequently chosen in development settings to support consistent material handling and reproducible reaction setup when preparing these downstream functionalized intermediates.
3. Complex Peptide Library Synthesis
Boc-D-Dab(Aloc)-OH*DCHA is frequently incorporated into workflows for peptide library construction where multiple analogs share a common protected backbone segment but diverge at the side-chain modification step. Custom peptide synthesis groups value the orthogonal protection pattern because it helps standardize early assembly conditions while preserving the ability to diversify the D-Dab side-chain after a programmed deprotection event. This makes the reagent particularly useful for generating series of D-Dab-modified peptides used in structure-activity relationship studies, chemical biology tool development, and SAR-driven optimization campaigns that require precise control over the timing of side-chain availability.
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