Fmoc-D-Cyclohexylglycine is a protected amino acid derivative featuring a cyclohexyl-substituted glycine backbone, where the side chain is a bulky hydrophobic cyclohexyl group rather than a standard proteinogenic residue. The molecule contains an amino function and a carboxyl group masked for peptide chemistry by the Fmoc (9-fluorenylmethoxycarbonyl) protecting group on nitrogen, and the "D" designation indicates the D stereochemical configuration at the alpha carbon. Fmoc-D-Cyclohexylglycine is used as a building block for stepwise peptide synthesis, particularly in solid-phase peptide synthesis workflows, where the Fmoc group supports controlled deprotection and the cyclohexyl side chain provides conformational and hydrophobic character in the resulting peptide chain.
CAT No: CP21107
CAS No:198543-96-3
Synonyms/Alias:Fmoc-D-Chg-OH;198543-96-3;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclohexylaceticacid;AmbotzFAA1666;AC1OCVEA;SCHEMBL13697519;CTK8C5025;MolPort-006-705-642;ACT10116;ZINC1036846;0203AB;ANW-73785;AKOS015911157;RTR-009229;AJ-24721;AK-80439;TR-009229;ST24035201;J-300446;I14-38622;(2R)-2-cyclohexyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)aceticacid;(R)-cyclohexyl({[(9H-fluoren-9-ylmethoxy)carbonyl]amino})aceticacid
Fmoc-D-Cyclohexylglycine is a D-configured, Fmoc-protected amino acid derivative in which the amino group is masked as a fluorenylmethoxycarbonyl (Fmoc) carbamate and the carboxyl function remains available for peptide coupling as an activated acid or protected acid variant. The molecule features a chiral center at the alpha carbon, a glycine-like backbone, and a bulky cyclohexyl side chain that increases hydrophobic surface area and stereochemically constrains conformational preferences in peptide and peptidomimetic scaffolds. The Fmoc group provides orthogonal protection compatible with standard base-labile deprotection strategies during solid-phase peptide synthesis, while the cyclohexyl substituent can participate in hydrophobic packing and influence aggregation behavior. The resulting reactivity profile supports its use as a chiral building block for amino acid derivatization, peptide construction, and downstream synthetic intermediate preparation in both research and process-oriented fine chemical workflows.
1. Peptide Synthesis
Fmoc-D-Cyclohexylglycine is applied in peptide synthesis where the Fmoc-protected amine enables controlled N-alkylation and stepwise chain assembly under Fmoc/tBu-type protecting-group logic. The D-stereochemistry at the alpha carbon and the cyclohexyl side chain help define local backbone geometry and hydrophobic interactions, which are relevant when incorporating conformationally biased residues into peptides and peptidomimetics. The carboxyl functionality supports peptide coupling chemistry to form stable amide bonds, allowing integration as a single residue or as part of longer sequences. The protected amino acid format also supports scalable intermediate preparation for peptide building block inventories used in research and industrial peptide manufacturing.
2. Peptidomimetics And SAR
Fmoc-D-Cyclohexylglycine is utilized in peptidomimetics and structure-activity relationship studies where a bulky, nonpolar cyclohexyl side chain can modulate binding pocket complementarity and conformational sampling. The D-configuration provides a stereochemical handle that can be compared against L-analogues to map stereochemical requirements in SAR workflows and to tune peptide-like scaffolds toward improved stability against proteolysis. The Fmoc-protected amino acid derivative integrates into synthesis of analog libraries using standardized coupling cycles, supporting rapid generation of residue-substituted variants. The resulting analogs can then be carried forward into biochemical assays and medicinal chemistry optimization campaigns as well-defined, structurally traceable intermediates.
3. Side-Chain Functionalization
Fmoc-D-Cyclohexylglycine serves in side-chain functionalization strategies where the cyclohexyl group acts as a hydrophobic anchor for subsequent chemical modification routes that introduce additional functionality without altering the amino acid backbone stereocenter. The Fmoc carbamate can be removed to reveal the free amine for orthogonal derivatization steps, while the carboxyl group can be converted into coupling-ready forms for incorporation into larger constructs. The combination of a protected amino acid framework and a nonfunctional cyclohexyl side chain supports conversion into substituted cyclohexyl derivatives through downstream transformations that preserve the D-configuration. The produced functionalized amino acid derivatives can be used to generate labeled or tagged peptide segments, hydrophobic pharmacophore elements, or intermediate fragments for specialty chemical production.
4. Chemical Biology Probes
Fmoc-D-Cyclohexylglycine is suitable for chemical biology probe construction where Fmoc-enabled peptide assembly allows incorporation of hydrophobic residues that influence membrane association, probe localization, and nonspecific binding profiles. The Fmoc-protected amine and chiral alpha center support synthesis of well-defined probe scaffolds with controlled stereochemistry, while the cyclohexyl side chain can be used to tune physicochemical properties such as lipophilicity and conformational rigidity. The protected amino acid format supports iterative coupling for attaching recognition motifs, linkers, and affinity handles into probe peptides. The resulting probe intermediates can be employed in biochemical research workflows that require reproducible stereochemical identity and peptide-compatible chemistry for downstream conjugation.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-D-Cyclohexylglycine is used in pharmaceutical manufacturing contexts as a chiral, Fmoc-protected amino acid intermediate for producing peptide drug candidates, peptide conjugates, and process-controlled reference materials. The Fmoc group provides a robust temporary protection strategy that is compatible with automated peptide synthesis platforms and supports predictable deprotection behavior during manufacturing-scale assembly. The D-cyclohexylglycine residue can be incorporated to modulate hydrophobicity and conformational preferences of peptide intermediates, which is relevant for formulation behavior and stability considerations during downstream processing. The compound's protected amino acid structure also supports batch-oriented fine chemical synthesis planning, including intermediate handling and incorporation into defined peptide sequences for analytical and production use.
6. Analytical Standards
Fmoc-D-Cyclohexylglycine is applied in analytical research as a stereochemically defined amino acid building block for method development, reference standard preparation, and mass spectrometric characterization of peptide fragments containing cyclohexylglycine residues. The Fmoc protection state and the D-configuration provide unambiguous structural identity that can be leveraged to validate deprotection and coupling outcomes in peptide workflows. The cyclohexyl side chain contributes distinctive hydrophobic fragmentation patterns that can aid targeted LC-MS/MS monitoring of peptide synthesis intermediates and final products. The availability of a protected, chiral amino acid derivative also supports preparation of calibration materials and internal standards for quality control in peptide-focused analytical laboratories and industrial process development teams.
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