Boc-L-Asp(tBu)-OH*DCHA is a protected amino acid derivative based on L-aspartic acid in which the α-amino group is protected as a Boc carbamate and the side-chain carboxyl group is masked as a tert-butyl ester. The molecule contains both an activated carboxyl functionality at the α-position (as the free acid) and a tert-butyl-protected side-chain carboxyl, while the "*DCHA" indicates association with dicyclohexylamine to form a salt that can influence handling and crystallinity. This compound is used as a stepwise building block for peptide synthesis and related amide-forming couplings, where orthogonal protection of the side-chain carboxyl supports controlled chemoselectivity during sequential assembly and subsequent deprotection strategies.
CAT No: CP25512
CAS No:1913-12-8
Synonyms/Alias:Boc-Asp(OtBu)-OHDCHA;1913-12-8;Boc-Asp(OtBu)-OH.DCHA;Boc-d-asp(otbu)-oh.dcha;Boc-Asp(OtBu)-OHinvertedexclamationmarkcurrencyDCHA;SCHEMBL3311032;MolPort-006-113-759;C13H23NO6.C12H23N;EINECS217-626-7;CB-329;AK-85718;Boc-Asp(OtBu)-OHdicyclohexylammoniumsalt;FT-0629742;FT-0688935;ST24046202;(2S)-4-(tert-butoxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoicacid;dicha;N-alpha-t-Butyloxycarbonyl-L-asparticacidbeta-t-butylesterdicyclohexylamine;4-tert-ButylhydrogenN-((tert-butoxy)carbonyl)-L-aspartate,compoundwithdicyclohexylamine(1:1)
Chemical Name:N-alpha-t-Butyloxycarbonyl-L-aspartic acid beta-t-butyl ester dicyclohexylamine
Boc-L-Asp(tBu)-OH*DCHA is a protected L-aspartic acid derivative used as a building block for peptide synthesis, featuring a Boc-protected alpha-amino group and a tert-butyl-protected side-chain carboxylate to preserve Asp functionality during coupling. The product is supplied as a DCHA salt form, which is commonly selected to improve handling and consistent performance in peptide-manufacturing workflows. Its protected acidic side chain makes it a practical choice for assembling Asp-containing sequences while maintaining side-chain integrity until the intended deprotection step.
1. Solid-Phase Peptide Synthesis
Boc-L-Asp(tBu)-OH*DCHA is commonly used in solid-phase peptide synthesis workflows to introduce aspartate residues with controlled side-chain protection. Peptide synthesis teams select this protected Asp building block to minimize side reactions from the side-chain carboxylate and to support reliable stepwise chain elongation. The Boc protection pattern aligns with Boc-based peptide assembly strategies, while the tBu side-chain protection helps prevent premature side-chain deprotection under standard coupling and washing conditions used during resin-bound synthesis. This makes the reagent particularly relevant for producing Asp-rich peptides and peptide segments where side-chain preservation is critical for downstream purification and final peptide quality.
2. Aspartate-Containing Segment Coupling
Boc-L-Asp(tBu)-OH*DCHA is frequently employed for segment condensation and solution-phase coupling steps where defined Asp residues must be incorporated into larger peptide fragments. In custom peptide manufacturing and medicinal chemistry research, the reagent's protected side-chain carboxylate supports selective reactivity at the alpha-amino functionality, helping maintain sequence fidelity during fragment assembly. The DCHA salt form is typically chosen to support consistent reagent behavior in peptide coupling workflows, which can be important when scaling synthesis or running parallel library preparations. Researchers rely on this building block when the target sequence requires aspartate side-chain retention until the final global deprotection stage.
3. Protected Amino Acid Intermediate Development
Boc-L-Asp(tBu)-OH*DCHA is also used as a key protected amino acid intermediate for preparing aspartate-containing intermediates used in downstream peptide and peptidomimetic development. Pharmaceutical intermediate teams and process chemists often select this specific protection scheme because it provides a stable, orthogonally protected Asp equivalent that can be carried through intermediate transformations without uncontrolled side-chain reactivity. The Boc/tBu protection pattern supports controlled deprotection planning, enabling the production of defined Asp-functional fragments or protected derivatives that later feed into peptide synthesis, conjugation-ready peptide intermediates, or other aspartate-bearing chemical building blocks used in research-grade synthesis campaigns.
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