Fmoc-D-Cpg-OH is an Fmoc-protected, D-configured amino acid derivative featuring a carboxylic acid (-COOH) and a free amino-reactive center masked by the 9H-fluoren-9-ylmethoxycarbonyl (Fmoc) group, with the side chain characteristic of Cpg (CpG) amino acid functionality. The molecule contains the Fmoc carbamate protecting group on the amino nitrogen, which controls chemoselectivity by suppressing side reactions during coupling steps, while retaining the carboxyl group for formation of peptide bonds and the D stereochemical configuration as specified by the name. In peptide chemistry and solid-phase peptide synthesis workflows, it is used as a protected building block to introduce the Cpg side-chain motif into peptide sequences for structure-activity studies, chemical biology labeling, or preparation of modified peptide analogues.
CAT No: CP25326
CAS No:13555-16-3
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-cyclopentylglycine
Fmoc-D-Cpg-OH is an Fmoc-protected D-configured amino acid derivative in which the side chain is built on a cyclic pyrrolidine-like motif (Cpg) and the molecule presents a free carboxylic acid for downstream coupling chemistry. The stereogenic center at the D-amino acid backbone is retained under standard peptide-synthesis conditions, supporting stereochemically defined incorporation into peptide sequences and peptidomimetic scaffolds. The fluorenylmethoxycarbonyl (Fmoc) group masks the amino functionality during chain assembly and can be removed under base to regenerate a reactive amine for iterative peptide coupling cycles. The free acid and heterocyclic side chain provide a chemically distinct handle for side-chain functionalization, salt formation, and conversion into amide or ester derivatives used as synthetic intermediates in amino acid derivatization workflows.
1. Peptide Synthesis
Fmoc-D-Cpg-OH is used in peptide building-block preparation for solid-phase peptide synthesis and related protected amino acid chemistry where controlled N-deprotection and coupling are required. The Fmoc-protected amine enables stepwise chain elongation while the D-configuration supports stereodefined peptide backbone construction and the Cpg side-chain heterocycle can influence local conformation and intramolecular interactions. The free carboxylic acid participates in standard peptide coupling chemistry to form amide bonds, allowing incorporation as a single residue or as part of peptide analog series. Downstream, the resulting protected peptide fragments can be deprotected and assembled into longer sequences for research-grade peptide science and synthetic methodology development.
2. Peptidomimetics And SAR
Fmoc-D-Cpg-OH serves as a chiral residue source for peptidomimetic construction and structure-activity relationship studies where side-chain topology and stereochemistry govern molecular recognition. The cyclic Cpg side chain provides a constrained functional architecture that can be retained during scaffold synthesis, while the D-amino acid backbone offers a stereochemical handle for mapping epimer-dependent effects in analog libraries. The Fmoc protection strategy supports rapid parallel synthesis of residue-substituted variants, and the free carboxyl group enables conversion into amide-linked analogs for SAR panel generation. The ability to generate stereochemically consistent peptide-like scaffolds makes this amino acid derivative suitable for systematic medicinal chemistry exploration of conformational and binding determinants.
3. Side-Chain Functionalization
Fmoc-D-Cpg-OH can be applied to amino acid modification workflows that exploit the heterocyclic Cpg side chain as a platform for further derivatization. The protected N-terminus prevents undesired side reactions during functional group installation, while the free carboxylic acid enables selective activation for amide formation with targeting motifs, linkers, or reporter-bearing groups. The D stereocenter provides stereochemical fidelity when producing functionalized derivatives used as intermediates for conjugation-ready building blocks. Downstream synthetic utility includes preparing functional amino acid derivatives for fragment elaboration, linker optimization, and generation of libraries of side-chain-modified chiral scaffolds.
4. Chemical Biology Probes
Fmoc-D-Cpg-OH is suitable for chemical biology research that requires incorporation of chiral, residue-defined motifs into peptide probes and biomolecule-interacting constructs. The Fmoc group supports controlled assembly of probe peptides, and base-triggered deprotection enables iterative synthesis of defined sequences for use in binding studies, competition assays, or mechanistic investigations. The heterocyclic Cpg side chain can contribute to conformational constraint, which may affect probe stability and target engagement profiles in assay formats. The free carboxylic acid functionality supports downstream derivatization into conjugation intermediates such as amide-linked probe variants used for molecular recognition studies and biochemical research intermediate preparation.
5. Pharmaceutical Intermediate Preparation
Fmoc-D-Cpg-OH can be employed as a chiral amino acid intermediate in pharmaceutical manufacturing and fine chemical synthesis where Fmoc-protected building blocks are integrated into controlled synthetic routes. The combination of an Fmoc-protected amine and a free carboxylic acid aligns with scalable peptide-coupling strategies used to assemble protected intermediates without premature functional group cross-reactivity. The D stereochemistry enables production of stereopure intermediates for downstream conversion into peptidic or peptidomimetic drug-like fragments, including C-terminal modifications through carboxyl activation and amide bond formation. The resulting intermediates can be carried forward into broader industrial synthetic sequences for specialty chemical production requiring defined chiral content and protected-group compatibility.
6. Process Chemistry Intermediate
Fmoc-D-Cpg-OH is applicable to process chemistry intermediate preparation where reproducible protection/deprotection cycles and robust coupling chemistry are required for manufacturing-grade peptide fragment synthesis. The Fmoc group provides a predictable orthogonal protection strategy for N-functionalization, while the D-configured backbone helps maintain stereochemical integrity across multistep assembly and purification operations. The heterocyclic Cpg side chain can influence solubility and solid-state behavior of intermediates, which is relevant for process design, crystallization screening, and downstream isolation of protected peptide units. The compound's structure supports conversion into activated derivatives for controlled amide formation, enabling consistent generation of chiral peptide building blocks used in applied product development and industrial chemistry workflows.
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