Boc-3-Cyano-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a D-phenylalanine backbone bearing a 3-cyano substituent on the aromatic ring and an N-terminal Boc (tert-butoxycarbonyl) protecting group. The molecule contains both an amino functionality masked as the Boc carbamate and a carboxyl group suitable for peptide coupling, while the cyano-bearing phenyl side chain provides a nitrile group that can influence polarity and serve as a chemically distinctive handle in structure-activity and labeling studies. In peptide chemistry, this protected amino acid is used as a building block for incorporating the cyano-substituted aromatic residue into peptides via stepwise synthesis, where the Boc group helps control chemoselectivity during assembly of more complex amino acid and peptide derivatives.
CAT No: CP11805
CAS No:205445-56-3
Synonyms/Alias:205445-56-3;Boc-D-Phe(3-CN)-OH;Boc-D-3-Cyanophenylalanine;(R)-2-((tert-Butoxycarbonyl)amino)-3-(3-cyanophenyl)propanoicacid;Boc-3-cyano-D-phenylalanine;(2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-cyanophenyl)propanoicacid;Boc-D-3-Cyanophe;AC1ODUIY;AC1Q1MTK;KSC913M8F;14985_ALDRICH;SCHEMBL5067241;14985_FLUKA;CTK8B3682;MolPort-002-344-036;ZINC2569508;ANW-42939;CB-751;AKOS015836552;AM82768;RTR-009587;(R)-N-BOC-3-3CYANOPHENYLALANINE;AK163624;AM019877;KB-48203
Boc-3-Cyano-D-Phenylalanine is a D-configured phenylalanine building block bearing a Boc-protecting group on the amino functionality and a side-chain 3-cyano substituent that increases polarity and provides a chemically distinctive handle for downstream derivatization. This protected amino acid is commonly used in peptide chemistry and medicinal-chemistry intermediate development where stereochemical control and a nitrile-bearing aromatic side chain are required. The cyano group also makes the compound a useful precursor for converting to other functional groups during structure-activity relationship (SAR) workflows.
1. Peptide Library Building
Boc-3-Cyano-D-Phenylalanine is used by peptide chemistry groups to introduce a D-amino acid residue with a nitrile-substituted phenyl side chain into short peptides and focused peptide libraries. The Boc protection supports standard protected-amino-acid workflows for assembling defined sequences, while the D-configuration helps researchers probe stereochemical effects on conformation, stability, and structure-property relationships. In library formats, the nitrile-bearing side chain provides a site for later chemical diversification without changing the peptide backbone identity.
2. Medicinal Chemistry SAR Intermediate
Boc-3-Cyano-D-Phenylalanine is frequently selected by medicinal-chemistry teams as a stereochemically defined intermediate for building peptidomimetic scaffolds and SAR series that require a nitrile-functional aromatic side chain. The cyano group can serve as a functional handle for subsequent transformations into alternative side-chain chemotypes, enabling systematic exploration of electronics and hydrogen-bonding patterns in lead optimization campaigns. Because the amino group is protected, the compound is also convenient for stepwise synthesis routes that culminate in coupling to larger fragments or incorporation into more complex intermediates.
3. Chiral Building Block Derivatization
Boc-3-Cyano-D-Phenylalanine supports chemical biology and synthetic chemistry programs that need a chiral, protected amino acid building block for derivatization strategies beyond direct peptide incorporation. The combination of Boc protection and a side-chain nitrile allows researchers to carry the stereochemical element through multiple synthetic steps while selectively modifying the side chain to access related analogs. This makes it useful for preparing families of D-phenylalanine analogs used in structure-activity mapping, conformational studies, and comparative binding or stability experiments in non-clinical research settings.
4. Pharmaceutical Intermediate Manufacturing
Boc-3-Cyano-D-Phenylalanine is used in industrial and contract manufacturing environments as a defined stereochemical amino-acid intermediate for downstream synthesis of specialized peptide-derived or peptidomimetic intermediates. The protected amino functionality helps maintain compatibility with multi-step assembly processes, while the nitrile-substituted aromatic side chain aligns with common medicinal-chemistry design motifs that require precise functional group placement. Manufacturers and process development chemists often choose this type of building block when a controlled D-configuration and a nitrile-bearing side chain are required for consistent intermediate quality across batches.
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