Fmoc-Asn(Trt)-OPfp is an Fmoc-protected asparagine derivative bearing an N-trityl (Trt) side-chain protection and an OPfp ester at the carboxyl terminus, placing it in the class of protected amino acid building blocks for peptide synthesis. The molecule contains an Fmoc carbamate on the amino group, a side-chain amide characteristic of asparagine, and a carboxyl group converted to an activated pentafluorophenyl (OPfp) ester, which presents a leaving-group handle while the Trt group helps suppress side reactions involving the side-chain functionality. In synthesis, it is employed as a peptide-coupling intermediate to enable controlled formation of amide bonds under conditions compatible with carboxyl-activated esters, supporting stepwise construction of peptides and related amino acid conjugates.
CAT No: CP26307
CAS No:132388-64-8
Synonyms/Alias:fmoc-asn(trt)-opfp;132388-64-8;(S)-Perfluorophenyl2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-oxo-4-(tritylamino)butanoate;CTK8B8755;MolPort-016-580-291;ANW-61185;CF-230;ZINC150339082;RTR-004430;AK-57842;FT-0629893;ST24036376;N-|A-Fmoc-N-|A-trityl-L-asparaginepentafluorophenylester
Fmoc-Asn(Trt)-OPfp is an Fmoc-protected asparagine derivative bearing a Trt (trityl) protected side-chain amide and an OPfp (pentafluorophenyl ester) activated carboxylate. The molecule combines a stable N-Fmoc carbamate for orthogonal peptide coupling control with a chiral amino acid framework whose stereochemistry is preserved during downstream activation steps. The Trt group shields the side-chain amide nitrogen to suppress undesired branching or cross-coupling, while the OPfp ester provides a highly reactive acylating handle that can participate in peptide bond formation under conditions compatible with protected amino acid chemistry. Pentafluorophenyl leaving-group character and the presence of multiple protecting groups make the compound a practical intermediate for assembling amide-rich structures and for preparing defined peptide fragments with controlled functional group exposure.
1. Peptide Synthesis
Fmoc-Asn(Trt)-OPfp supports peptide building block preparation in solid-phase or solution-phase workflows where orthogonal protection is required for asparagine residues. The Fmoc group enables standard N-terminal deprotection and re-protection logic, while the Trt-protected side-chain amide helps maintain single-site reactivity during coupling. The OPfp ester functions as an activated carboxylate, facilitating peptide coupling chemistry that preserves the asparagine side-chain from premature modification. Defined incorporation of Asn analogs with protected side-chain functionality can be used to construct peptide sequences for biochemical research, peptide library generation, and sequence-specific fragment assembly in synthetic organic chemistry.
2. Protected Amino Acid Chemistry
Fmoc-Asn(Trt)-OPfp is suited to protected amino acid intermediate preparation where controlled functional group masking is central to reproducible synthesis. The N-Fmoc carbamate and Trt-protected side-chain amide provide orthogonal protection patterns that can be selectively removed or transformed to reveal functional sites at planned stages of synthesis. The OPfp ester gives an acylating moiety that can be converted into peptide bonds or related amide linkages without exposing the carboxylate as a less reactive handle. Downstream derivatization of this chiral amino acid derivative can support stepwise synthesis of asparagine-containing motifs, including peptidomimetic scaffolds and defined amide-rich intermediates used for further chemical elaboration.
3. Peptidomimetics And SAR Studies
Fmoc-Asn(Trt)-OPfp can be applied to peptidomimetic construction and structure-activity relationship studies requiring precise placement of asparagine side-chain amide functionality. The protected side-chain amide (Trt) helps maintain the hydrogen-bonding motif during coupling, enabling assembly of analog series where amide orientation and local polarity are systematically varied. The OPfp activation supports rapid generation of amide-linked fragments that can be incorporated into constrained scaffolds or substituted peptide analogs. Defined Asn incorporation supports SAR workflows by enabling consistent synthesis of analog sets for analytical characterization and comparative molecular design.
4. Chemical Biology Conjugation
Fmoc-Asn(Trt)-OPfp serves chemical biology workflows where protected asparagine residues are introduced into peptide conjugates and labeling substrates. The combination of Fmoc protection and side-chain amide masking enables controlled installation of Asn-containing segments into larger bioconjugation constructs before final deprotection and functional unveiling. The OPfp ester provides an activated acyl group that can participate in amide bond formation to link peptide fragments, affinity handles, or linker-bearing moieties while minimizing side reactions from unprotected nucleophiles. Resulting conjugate precursors can be used to generate labeled biomolecule probes, affinity reagents, and defined peptide-based materials used in biochemical research.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-Asn(Trt)-OPfp is applicable to pharmaceutical manufacturing intermediate preparation for peptide and peptide-like intermediates where protecting-group strategy and coupling compatibility affect process robustness. The Fmoc group supports controlled N-terminal deprotection steps, while Trt protection helps prevent side-chain participation during sequential assembly of asparagine-containing sequences. The OPfp ester's activated carboxylate character can be leveraged for efficient formation of amide bonds in process chemistry routes that require reproducible coupling of protected amino acids. Downstream generation of defined peptide fragments from this chiral intermediate can feed into larger manufacturing sequences for fine chemical production of peptide-based research materials and industrially manufactured peptide intermediates.
6. Analytical Research Standards
Fmoc-Asn(Trt)-OPfp can be used in analytical research and method development where protected amino acid derivatives serve as reference materials for LC-MS, HPLC, and peptide coupling monitoring. The presence of Fmoc, Trt, and the pentafluorophenyl ester provides distinctive mass and fragmentation features that can aid identification of intermediates and confirmation of coupling completeness in protected amino acid chemistry. The orthogonal protection pattern supports controlled conversion to predictable products during sample preparation for analytical characterization. Consistent structure and defined protecting groups help support quality-by-design analytical workflows for peptide building block preparation, impurity profiling, and verification of protected amino acid transformation steps.
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