Fmoc-D-Gln-OPfp is an Fmoc-protected D-form glutamine amino acid derivative bearing a side-chain amide characteristic of glutamine and a carboxyl group converted to an OPfp ester (pentafluorophenyl ester). The molecule contains an Fmoc carbamate on the amino functionality and an OPfp group on the carboxylate, providing a protected amino acid framework with a stereochemical configuration specified as D and a side-chain capable of hydrogen-bonding through its amide. As an activated amino acid ester, it is employed in peptide synthesis workflows to enable controlled coupling of the glutamine residue while the Fmoc group supports stepwise assembly and chemoselective handling of the protected functional groups.
CAT No: CP26659
CAS No:200622-33-9
Synonyms/Alias:fmoc-d-gln-opfp;200622-33-9;Fmoc-D-GlutaminePentafluorophenylEster;CTK3J8347;MolPort-016-580-298;CF-794;ZINC71788104;AK-85724;KB-302489;RT-004544;A7883;FT-0686522;ST24047252;PentafluorophenylN~2~-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-glutaminate;(2,3,4,5,6-pentafluorophenyl)(2R)-5-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoate
Fmoc-D-Gln-OPfp is an Fmoc-protected D-glutamine derivative bearing an OPfp ester (pentafluorophenyl ester) on the side-chain carboxylamide functionality, combining an N-fluorenylmethoxycarbonyl protecting group with a highly activated leaving group for acyl transfer chemistry. The molecule retains the chiral D-configuration at the glutamine alpha-carbon, while the Fmoc group supports standard base-labile deprotection in peptide synthesis workflows. The OPfp ester is electron-deficient and prone to nucleophilic acyl substitution, enabling controlled conversion to side-chain amide or related acylated intermediates under appropriate conditions. The presence of both a protected amine (via Fmoc) and a reactive activated ester makes Fmoc-D-Gln-OPfp a chiral, derivatizable intermediate suited for peptide building block preparation and downstream functionalization.
1. Peptide Synthesis
Fmoc-D-Gln-OPfp is applied in solid-phase and solution-phase peptide synthesis where Fmoc chemistry enables orthogonal N-protection and predictable coupling behavior. The Fmoc-protected amino group supports iterative chain assembly after base-mediated deprotection, while the glutamine-derived side-chain architecture provides the amide-containing functionality used to model polar residues in peptide backbones. The OPfp ester can participate in acyl transfer or side-chain activation strategies that help access glutamine-like side-chain states during protected amino acid synthesis and intermediate preparation. The D-stereochemical configuration supports stereochemically defined peptide analog construction for studies requiring non-natural stereochemistry at glutamine positions.
2. Amino Acid Derivatization
Fmoc-D-Gln-OPfp is used as an amino acid derivatization intermediate for generating acylated glutamine derivatives and for introducing side-chain modifications through OPfp-mediated acylation chemistry. The OPfp ester's pentafluorophenyl leaving group facilitates nucleophile-driven acyl substitution, allowing conversion to alternative side-chain amide forms or related protected acyl intermediates compatible with peptide chemistry. The combination of a stable Fmoc carbamate and a reactive ester enables stepwise protection and functional-group interconversion without losing the chiral center. Downstream products prepared from this intermediate can serve as building blocks for unnatural amino acid incorporation, peptide analog libraries, and structure-defined chemical probes.
3. Bioconjugation Chemistry
Fmoc-D-Gln-OPfp can be employed in bioconjugation workflows that require site-specific linkage formation from amino acid-derived activated esters. The OPfp ester supports acylation reactions with nucleophiles such as amines or other functional groups present on biomolecular targets, enabling construction of peptide-protein, peptide-polymer, or peptide-surface conjugates with glutamine-derived linkers. The Fmoc group provides a handle for controlled deprotection when conjugation strategies are integrated with peptide fragments, permitting sequential assembly of conjugates from protected building blocks. The D-glutamine stereochemistry can be leveraged to tune stability and resistance to proteolysis in conjugate designs used for chemical biology research and material-functionalization programs.
4. Peptidomimetics Construction
Fmoc-D-Gln-OPfp is suitable for peptidomimetic construction where polar glutamine side-chain geometry and stereochemistry are used to modulate molecular recognition. The protected amino acid framework enables incorporation into peptide analogs via standard coupling logic after Fmoc removal, while the side-chain functionalization potential of the OPfp ester supports preparation of alternative amide-bearing motifs. The D-configuration at the alpha-carbon supports design of stereochemically constrained analogs that can probe backbone-dependent binding modes in SAR studies and chemical biology investigations. Resulting peptidomimetics can be advanced into fragment-based optimization campaigns and scaffold diversification efforts where chiral amino acid intermediates are required.
5. Pharmaceutical Manufacturing
Fmoc-D-Gln-OPfp is relevant to pharmaceutical manufacturing and fine chemical production routes that rely on protected amino acid intermediates for controlled synthesis of peptide-based or peptide-derived materials. The Fmoc protecting group supports robust handling and predictable deprotection under peptide-manufacturing conditions, while the OPfp ester enables conversion to glutamine side-chain derivatives used in downstream assembly steps. The stereochemically defined D-glutamine core supports consistent batch-to-batch stereochemical integrity for manufacturing of chiral peptide intermediates and related active or intermediate constructs. Industrial process chemistry can incorporate this type of activated amino acid derivative to streamline preparation of protected building blocks and to support scalable synthesis of functional peptide fragments.
6. Analytical Research Standards
Fmoc-D-Gln-OPfp is used in analytical research as a chiral, structurally defined reference intermediate for method development and characterization of Fmoc-amino acid derivatives. The combination of Fmoc chromophore and the OPfp ester provides distinct analytical signatures that can support LC-MS, HPLC method qualification, and monitoring of protected amino acid transformations during peptide building block preparation. The D-stereochemistry and glutamine-derived side-chain functionality allow stereospecific comparisons when evaluating deprotection, coupling compatibility, or ester-to-amide conversion pathways. Analytical standards derived from this intermediate can also support impurity profiling and structural verification in amino acid derivative manufacturing and peptide synthesis development.
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