Fmoc-Trp-OPfp contains the indole side chain of tryptophan linked to a carboxyl group converted into an OPfp ester (pentafluorophenyl ester) while the alpha-amino functionality is protected as an Fmoc carbamate. The molecule therefore bears an Fmoc-protected nitrogen for controlled amide bond formation during peptide assembly and an OPfp-activated carboxyl group that functions as an electrophilic acylating handle, with the indole ring providing aromatic and potential π-stacking interactions. In synthesis and chemical biology workflows, Fmoc-Trp-OPfp is employed as a protected amino acid derivative for stepwise peptide synthesis or for preparing acylated intermediates and activated conjugation partners under conditions compatible with carbamate and pentafluorophenyl ester chemistry.
CAT No: CP27543
CAS No:86069-87-6
Synonyms/Alias:Fmoc-Trp-OPfp;86069-87-6;Fmoc-L-tryptophanpentafluorophenylester;47479_ALDRICH;SCHEMBL3505124;47479_FLUKA;CTK8C6855;L-Tryptophan,N-[(9H-fluoren-9-ylmethoxy)carbonyl]-,2,3,4,5,6-pentafluorophenylester;MolPort-003-934-132;CF-227;ZINC71788076;AKOS015853407;AKOS015902756;RTR-026849;AK-81224;KB-302487;TR-026849;FT-0642032;ST24047307;I14-19908;PentafluorophenylN-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-tryptophanate
Fmoc-Trp-OPfp is an Fmoc-protected tryptophan derivative in which the side-chain indole and the α-amino group are protected for peptide chemistry, while the carboxyl functionality is converted to an OPfp (pentafluorophenyl ester). As a chiral amino acid building block, it presents a stereodefined α-carbon and a protected indole-containing side chain that can participate in noncovalent interactions during peptide assembly and downstream binding studies. The OPfp ester is an activated carboxylate equivalent that undergoes acyl transfer under peptide-coupling conditions, enabling efficient formation of amide bonds while remaining compatible with Fmoc-based solid-phase or solution-phase strategies. The combination of Fmoc for orthogonal N-protection and the fluorinated OPfp leaving group supports controlled peptide synthesis, intermediate derivatization, and analytical tractability through the distinctive pentafluorophenyl motif.
1. Peptide Synthesis
Fmoc-Trp-OPfp is applied in peptide synthesis workflows where Fmoc protection and an activated carboxylate are required for reliable peptide coupling. The α-carboxyl OPfp ester functions as an acylating handle, while the Fmoc group stabilizes the nitrogen for stepwise N-deprotection and re-coupling cycles. The tryptophan indole side chain remains present during assembly, allowing incorporation of aromatic side-chain chemistry into linear peptides and peptide fragments. The resulting amide bond formation supports preparation of tryptophan-containing peptide building blocks for research-grade libraries and for manufacturing-scale peptide intermediate generation.
2. Protected Amino Acid Chemistry
Fmoc-Trp-OPfp is suitable for protected amino acid chemistry and amino acid ester-to-amide conversion strategies that rely on orthogonal protection logic. The Fmoc group provides an N-protection handle compatible with base-mediated deprotection, while the OPfp ester provides a reactive C-terminal equivalent that can be transformed into peptide bonds without directly exposing a free carboxylic acid. The fluorinated pentafluorophenyl ester can be used as a controlled intermediate for preparing C-terminally modified peptide fragments, including sequences requiring tryptophan at defined positions. The stereodefined α-carbon and preserved indole functionality help maintain structural fidelity in downstream peptide analog synthesis and synthetic intermediate preparation.
3. Peptidomimetics And SAR Studies
Fmoc-Trp-OPfp is used in peptidomimetic and structure-activity relationship (SAR) studies where tryptophan residues and aromatic side-chain presentation are key to molecular recognition. The indole moiety enables modeling of π-stacking and hydrogen-bonding patterns, while the activated OPfp ester supports rapid assembly of amide-linked analogs with varied neighboring residues. The Fmoc-protected amino acid derivative format supports combinatorial construction of peptide-like scaffolds and constrained analogs by enabling sequential coupling and controlled N-terminal processing. The ability to generate defined tryptophan-containing intermediates supports SAR workflows that require consistent stereochemistry and functional group placement for downstream characterization.
4. Chemical Biology Probes
Fmoc-Trp-OPfp is applied in chemical biology probe synthesis where tryptophan-containing peptides serve as recognition elements for labeling, affinity reagents, and binding studies. The indole side chain can be leveraged for noncovalent interactions with protein targets, while the OPfp ester enables formation of amide linkages to introduce probe-specific motifs at the peptide termini. Fmoc-based protection supports modular assembly of probe precursors, including peptide conjugates that later undergo functional group transformations outside the peptide backbone. The fluorinated OPfp group can also assist in analytical tracking during intermediate handling, supporting the preparation of well-defined biochemical research reagents.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-Trp-OPfp is relevant to pharmaceutical manufacturing and fine chemical synthesis routes that require controlled incorporation of tryptophan into protected peptide intermediates. The Fmoc protection strategy aligns with established peptide synthesis supply chains, and the OPfp ester provides a reactive carboxyl equivalent that can be converted into amide-linked product fragments under coupling conditions. The combination of stable N-protection and activated C-terminal functionality supports reproducible intermediate formation for downstream purification and conversion steps in peptide-based process chemistry. The stereodefined α-amino acid framework and intact indole side chain help maintain consistent structural attributes across manufactured peptide intermediates used for further synthetic elaboration.
6. Analytical Research Standards
Fmoc-Trp-OPfp is utilized in analytical research contexts as a chemically defined amino acid derivative standard and coupling intermediate for method development. The presence of both Fmoc and the pentafluorophenyl ester introduces distinctive chromatographic and mass spectrometric signatures that can support LC-MS identification of tryptophan-containing coupling products and impurities. The OPfp ester functionality provides a practical reference for monitoring acyl transfer efficiency and for verifying conversion pathways during amino acid ester-to-amide transformations. The protected, stereodefined structure supports reproducible analytical comparisons in peptide synthesis development, impurity profiling, and characterization of protected amino acid building blocks.
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