Boc-4-Cyano-L-Phenylalanine is an Fmoc/Boc-protected, amino acid derivative of L-phenylalanine bearing a para-cyano substituent on the aromatic side chain, placing it in the class of substituted phenylalanine analogues used for peptide building blocks. The molecule contains an N-Boc carbamate protecting group on the amino functionality and a free carboxylic acid, while the side chain features a nitrile group that provides a polar, chemically stable handle distinct from the parent phenylalanine benzyl side chain. In peptide synthesis workflows, the Boc-protected amino group supports stepwise coupling by controlling chemoselectivity, and the 4-cyano aromatic functionality can be used to introduce a defined electronic and polarity element for structure-activity studies, protein engineering constructs, or analytical standards.
CAT No: CP11904
CAS No:131724-45-3
Synonyms/Alias:131724-45-3;Boc-Phe(4-CN)-OH;Boc-L-4-Cyanophenylalanine;(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-cyanophenyl)propanoicacid;Boc-4-cyano-L-phenylalanine;SBB063884;(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-cyanophenyl)propanoicacid;(S)-N-Boc-4-Cyanophenylalanine;(2S)-3-(4-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoicacid;Boc-L-4-Cyanophe;N-Boc-4-cyanophenylalanine;AC1ODU11;Boc-p-cyano-L-phenylalanine;KSC925C6H;14988_ALDRICH;(N-Boc)-4-cyanophenylalanine;N-Boc-4-cyano-L-phenylalanine;SCHEMBL1350138;14988_FLUKA;CTK8C5163;MolPort-002-344-037;RMBLTLXJGNILPG-LBPRGKRZSA-N;ZINC2567679;ANW-74385;CB-479
Boc-4-Cyano-L-Phenylalanine is a Boc-protected amino acid building block derived from L-phenylalanine, featuring a para-cyano substituent on the aromatic ring. The Boc group provides an N-terminal protecting strategy commonly used to control reactivity during peptide assembly, while the electron-withdrawing cyano functionality offers a distinct handle for structure-property studies and downstream synthetic elaboration. This reagent is frequently selected when a cyano-bearing phenylalanine residue is required for medicinal chemistry, peptide analog generation, or intermediate preparation.
1. Peptide Building Block Use
Boc-4-Cyano-L-Phenylalanine is used as a protected amino acid residue for custom peptide synthesis where the target sequence requires a para-cyano-substituted phenylalanine side chain. Peptide chemists incorporate this building block into solution-phase or solid-supported workflows to generate analogs for SAR studies, receptor-binding motif optimization, and conformational or electronic tuning of aromatic side chains. The Boc protection helps maintain controlled N-terminus reactivity during coupling steps, while the cyano group remains present for later functionalization or for direct influence on physicochemical behavior in the assembled peptide.
2. Medicinal Chemistry Analog Synthesis
Boc-4-Cyano-L-Phenylalanine supports medicinal chemistry programs that require cyano-functionalized aromatic amino acid motifs as part of peptidomimetics, peptide-like inhibitors, or constrained scaffold fragments. Medicinal chemistry teams value the para-cyano substituent because it can modulate polarity and aromatic electronics, enabling rational diversification when exploring structure-activity relationships. As an amino acid derivative intermediate, it is commonly routed into downstream coupling, side-chain derivatization, or scaffold elaboration steps to access series of analogs with controlled substitution patterns.
3. Pharmaceutical Intermediate Development
Boc-4-Cyano-L-Phenylalanine is also used as a pharmaceutical intermediate building block for manufacturing-relevant synthesis of cyano-bearing aromatic fragments and protected amino acid derivatives. Process development and intermediate synthesis groups select this material when they need a stable, isolable protected form that carries both an N-protecting group and the para-cyano aromatic functionality for subsequent transformations. The defined substitution pattern makes it practical for preparing downstream intermediates used in specialty chemical manufacturing, including routes that require retention of the cyano group as a functional element through multiple synthetic stages.
4. Structure-Property Studies
Boc-4-Cyano-L-Phenylalanine is frequently employed in research settings focused on how aromatic substituents influence peptide or small-molecule properties, such as polarity, hydrogen-bonding capacity, and electronic effects. Chemical biology and materials-oriented researchers use cyano-bearing phenylalanine analogs to build well-defined structure sets for comparative studies, where the cyano group provides a consistent, measurable modification relative to unsubstituted phenylalanine derivatives. The Boc-protected form enables incorporation into defined synthetic constructs, supporting reproducible comparisons across analog series.
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