Boc-D-Dab(Boc)-OH*DCHA is a protected, stereochemically defined amino acid derivative featuring the D-configuration on the α-carbon and the Dab(Boc) side-chain motif, where both the amino functionality and the side-chain amino group are masked as Boc (tert-butoxycarbonyl) carbamates. The molecule contains a free carboxylic acid group while the Boc-protected amines reduce nucleophilicity and chemoselectively direct reactivity during peptide-coupling steps, and the "*DCHA" indicates association with dicyclohexylamine (DCHA) as a counterion/forming salt to support handling and solid-state properties. In synthetic peptide chemistry, this compound functions as a protected building block for incorporating a diamino-alanine-type residue with controlled side-chain protection, enabling stepwise construction of peptides or peptide fragments while minimizing side reactions from unprotected amino groups.
CAT No: CP25790
CAS No:350820-58-5
Synonyms/Alias:N-alpha-Boc-N-gamma-Boc-D-2,4-diaminobutyric acid*DCHA;Boc-D-Dab(Boc)*DCHA
Chemical Name:N-alpha-N-gamma-Bis(t-butyloxycarbonyl)-D-2,4-diaminobutyric acid dicyclohexylamine
Boc-D-Dab(Boc)-OH*DCHA is a stereodefined, doubly protected Dab (2,4-diaminobutyric acid) derivative supplied as a salt complex with DCHA, combining an N-Boc-protected amino acid framework with an additional Boc-protected side-chain amino group. This protection pattern is commonly used to control chemoselectivity during peptide assembly, while the salt form supports practical handling and consistent reactivity in downstream coupling workflows. The D-configuration makes it a valuable building block for stereochemical control in peptidomimetic and non-natural peptide architectures.
1. Fmoc-Free Peptide Building
Boc-D-Dab(Boc)-OH*DCHA is used by peptide synthesis groups that prefer Boc-based protection strategies or that need a Dab residue with controlled side-chain protection for segment condensation and custom peptide assembly. The N-Boc group and the Boc-protected side-chain amino functionality help maintain orthogonal reactivity during coupling steps, enabling reliable incorporation of a stereodefined D-Dab unit into peptide sequences. Researchers developing constrained or non-natural peptide scaffolds often select this reagent to manage the diamino side chain without premature side reactions that can occur with unprotected or partially protected analogs.
2. Peptidomimetic Side-Chain Control
Boc-D-Dab(Boc)-OH*DCHA supports peptidomimetic development where the diamino side chain must be preserved for later functional diversification after peptide assembly. In medicinal chemistry and chemical biology workflows, the protected Dab residue provides a stable handle for producing peptide analogs that can be further elaborated into derivatives (for example, by post-assembly deprotection and subsequent derivatization steps). The stereochemical definition of the D-center is particularly useful when researchers are tuning conformational preferences, backbone stereochemistry, or structure-activity relationship series where stereocontrol at the amino acid level is required.
3. Protected Amino Acid Intermediate Supply
Boc-D-Dab(Boc)-OH*DCHA is also used as a pharmaceutical-intermediate-grade amino acid building block for manufacturing and development of modified peptide fragments, where consistent protection and a defined salt form help standardize reagent behavior across batches. Process development teams and custom synthesis providers rely on such protected amino acid derivatives to reduce variability in coupling performance and downstream purification complexity when assembling complex sequences containing diamino residues. The Boc/Boc protection pattern aligns with workflows that require controlled deprotection later in the synthesis campaign, supporting scalable preparation of protected peptide intermediates for further chemical elaboration.
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