Boc-3-(2-Furyl)-D-alanine dicyclohexylamine is a protected, non-proteinogenic amino acid derivative featuring a D-configured alanine backbone bearing a 3-(2-furyl) side chain and an N-terminal Boc (tert-butoxycarbonyl) protecting group. The molecule contains both an amino functionality masked as the carbamate and a carboxyl group present as a dicyclohexylamine salt, with the furan ring providing an aromatic heterocycle handle for electronic and π-interaction studies in peptide-related contexts. It is used as a precursor in amino acid and peptide synthesis where the Boc group supports chemoselective stepwise coupling while the substituted side chain can be incorporated into engineered peptide analogues or employed in structure-activity and labeling experiments.
CAT No: CP21705
Boc-3-(2-Furyl)-D-alanine dicyclohexylamine is a D-configured, side-chain functionalized amino acid building block supplied as a dicyclohexylamine salt, with a Boc (tert-butoxycarbonyl) group on the amino functionality for controlled reactivity during peptide assembly. The 2-furyl substituent provides an aromatic heterocycle handle that is frequently leveraged in medicinal chemistry and peptide/peptidomimetic design to influence local interactions and conformational preferences. This protected form is commonly used when a stable, isolable amino acid intermediate is needed for downstream coupling into protected peptide fragments or for preparing analogs where the heteroaromatic side chain must be preserved.
1. Protected Peptide Fragment Building
Boc-3-(2-Furyl)-D-alanine dicyclohexylamine is used as a protected amino acid building block for assembling D-amino acid-containing peptide segments in both custom peptide synthesis and library workflows. The Boc protection supports reliable coupling strategies for constructing defined sequences while keeping the amino group masked until deprotection steps in the peptide synthesis cycle. The dicyclohexylamine salt form improves practical handling and weighability for routine synthesis planning, which is particularly useful when incorporating a heteroaromatic side chain that must remain intact throughout fragment assembly.
2. Peptidomimetic And SAR Analog Synthesis
Boc-3-(2-Furyl)-D-alanine dicyclohexylamine is frequently selected for medicinal chemistry programs that generate peptidomimetic analogs and structure-activity relationship (SAR) series containing D-amino acid residues. The 2-furyl side chain offers a compact heteroaromatic motif that can be retained through multistep synthesis to probe how aromatic heterocycles affect physicochemical properties and local binding-site interactions in lead optimization. As a protected, isolable intermediate, it fits well into workflows that require consistent incorporation of the same stereochemical and side-chain identity across multiple analogs.
3. Stereodefined D-Amino Acid Incorporation
Boc-3-(2-Furyl)-D-alanine dicyclohexylamine supports stereodefined construction of D-amino acid frameworks used to modulate peptide backbone properties and improve the structural definition of synthetic sequences. Researchers developing D-amino acid-enriched peptides for chemical biology toolkits and non-natural peptide scaffolds rely on protected building blocks to maintain sequence fidelity during iterative assembly. The combination of Boc protection and the furyl side chain enables incorporation of a specific stereochemical unit without requiring late-stage introduction of the heteroaromatic group, which helps streamline analog generation where the side chain must be preserved through coupling and deprotection cycles.
4. Aromatic Heterocycle Side-Chain Engineering
Boc-3-(2-Furyl)-D-alanine dicyclohexylamine is applied when an aromatic heterocycle side chain is needed as a functional element in synthetic peptides or peptide-like constructs. The 2-furyl group provides a chemically distinct aromatic handle that can participate in heteroaromatic interactions and serve as a structural probe within designed sequences. In materials and chemical biology contexts where defined side-chain presentation matters, this building block enables consistent placement of the furyl motif at a D-amino acid position, supporting downstream studies that compare sequence variants while keeping the heteroaromatic identity constant.
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