Fmoc-D-Trp-OPfp contains the indole side chain of D-tryptophan linked to an Fmoc-protected amino group and an OPfp ester at the carboxyl terminus, placing the molecule within the class of protected amino acid derivatives used for peptide-related synthesis. The structure features an Fmoc carbamate that masks the α-amino functional group and an OPfp (pentafluorophenyl ester) carboxyl activation motif that can undergo acyl transfer chemistry while the indole ring provides aromatic and potential π-stacking interactions. In synthesis workflows, this protected amino acid derivative functions as a stepwise building block for assembling peptides and peptide analogues on solid-phase or in solution, and the pentafluorophenyl ester handle can support coupling and derivatization strategies for preparing more complex amino acid and peptide intermediates.
CAT No: CP26341
CAS No:136554-94-4
Synonyms/Alias:fmoc-d-trp-opfp;136554-94-4;D-Tryptophan,N-[(9H-fluoren-9-ylmethoxy)carbonyl]-,2,3,4,5,6-pentafluorophenylester;MolPort-016-580-310;CF-852;ZINC71788111;AKOS025117407;AK163529;ST24047266;I14-18177
Fmoc-D-Trp-OPfp is an Fmoc-protected D-tryptophan OPfp ester, where the chiral D-tryptophan core bears an indole side chain and a stereogenic alpha carbon, while the carboxyl functionality is converted to an activated pentafluorophenyl (OPfp) ester. The molecule combines a base-stable Fmoc carbamate on the amino group with a highly electrophilic OPfp ester that can participate in acyl transfer reactions under peptide-coupling and derivatization conditions. The presence of both an indole aromatic system and a fluorinated leaving group supports downstream transformations that preserve stereochemical integrity at the alpha center when appropriate coupling conditions are used. The overall structure is engineered for peptide synthesis compatibility and for generating acylated intermediates that can be carried forward into amide bond formation and related amino acid derivative workflows.
1. Peptide Coupling
Fmoc-D-Trp-OPfp is used in peptide synthesis workflows as an activated carboxylate equivalent for rapid amide bond formation with amine nucleophiles. The Fmoc-protected D-tryptophan framework provides a protected N-terminus for orthogonal handling, while the OPfp ester serves as a reactive acylating group that can couple to side-chain or terminal amines to build peptide chains. The D-configuration at the alpha carbon enables stereochemically defined incorporation of D-Trp into peptides and peptide-like constructs, supporting studies where epimeric control is required. Downstream, the resulting Fmoc-bearing peptide fragments can be carried through standard deprotection and coupling sequences to generate D-amino acid-containing peptides and analogs for research-grade scaffold construction and process-compatible peptide intermediate preparation.
2. Peptidomimetics And SAR
Fmoc-D-Trp-OPfp supports peptidomimetic and structure-activity relationship studies by enabling controlled installation of a D-tryptophan residue into bioactive peptide analogs. The indole side chain provides a distinct aromatic recognition element, while the stereodefined D-amino acid center helps probe conformational effects and protease resistance trends associated with D-residue incorporation. OPfp activation facilitates formation of amide linkages that can be used to assemble libraries of analogs with consistent coupling chemistry and defined connectivity. The Fmoc handle further supports iterative synthesis of longer sequences or constrained mimetics, enabling downstream generation of SAR-focused peptide scaffolds and fragment-linked intermediates used in medicinal chemistry campaigns.
3. Unnatural Amino Acid Incorporation
Fmoc-D-Trp-OPfp is applied for unnatural amino acid incorporation in chemical biology and protein engineering contexts where D-tryptophan is required at specific positions. The compound's chiral D-tryptophan architecture allows site-specific stereochemical placement, and the Fmoc-protected amine supports orthogonal protection strategies during stepwise assembly. The OPfp ester can be employed to couple the activated carboxyl group to nucleophilic amine partners, enabling construction of D-Trp-containing peptide segments that can later be deprotected, extended, or functionalized. Resulting D-amino acid-containing intermediates can be used to generate peptide substrates, binding probes, or engineered sequence variants that support mechanistic studies of stereochemical recognition and peptide processing.
4. Bioconjugation Chemistry
Fmoc-D-Trp-OPfp can be utilized in bioconjugation chemistry to introduce an indole-bearing, stereodefined acyl motif into amine-functional biomolecules or linkers. The OPfp ester functionality enables acyl transfer to primary amines, allowing formation of stable amide bonds that connect D-Trp-derived fragments to proteinogenic or synthetic amine handles. The indole moiety can serve as an aromatic anchor for conjugate design, while the Fmoc group provides a protected state that can be managed during multi-step synthesis before final deprotection or assembly into conjugates. Downstream, the resulting conjugation-ready intermediates can support preparation of labeled peptides, affinity reagents, or biomolecule-modified constructs used in biochemical research and analytical method development.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-D-Trp-OPfp is relevant to pharmaceutical manufacturing and fine chemical production as a defined, activated amino acid intermediate for constructing D-amino acid-containing peptide intermediates at scale. The combination of Fmoc protection and an OPfp activated ester supports reliable downstream amide bond formation while maintaining a protected N-function that aligns with industrial peptide synthesis strategies. The fluorinated OPfp leaving group supports efficient acyl transfer chemistry, and the stereochemically defined D-Trp core supports consistent incorporation into regulated peptide-like structures and processable intermediates. Resulting peptide fragments can be carried into further purification and conversion steps typical of industrial peptide intermediate preparation, enabling manufacturing routes for stereodefined peptide analogs used as research and development building blocks.
6. Analytical Research Standards
Fmoc-D-Trp-OPfp is suitable for analytical research and method development where stereodefined D-tryptophan-containing peptide fragments are required as reference materials. The Fmoc group and activated ester functionality support preparation of defined amide-linked standards that can be used to benchmark LC-MS/MS fragmentation patterns, retention behaviors, and derivatization outcomes for D-Trp-containing analytes. The indole aromatic side chain provides a strong chromatographic and mass spectrometric signal handle, while the OPfp activation enables consistent synthesis of reference structures with controlled connectivity. Downstream, the compound can be converted into labeled or derivatized peptide standards that support analytical verification of peptide synthesis outcomes, stereochemical integrity checks, and impurity mapping in amino acid derivative and peptide chemistry workflows.
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