Fmoc-Asn(Trt)-Ser(Psi(Me,Me)pro)-OH is a protected amino acid derivative used as a peptide-building block, featuring an asparagine residue bearing a Trt side-chain protecting group and a serine residue whose side-chain hydroxyl is modified with a Psi(Me,Me)pro substituent. The molecule contains an Fmoc carbamate protecting group on the amino functionality and a C-terminal carboxylic acid, with the side-chain functionalities masked to control chemoselectivity during peptide assembly. In synthetic peptide chemistry, this protected analogue is employed in stepwise peptide synthesis to introduce the specified Asn and Psi(Me,Me)pro-modified Ser motifs while minimizing undesired side reactions associated with unprotected amine and hydroxyl groups.
CAT No: CP27586
CAS No:920519-33-1
Synonyms/Alias:920519-33-1;Fmoc-Asn(Trt)-Ser{psi(Me,Me)pro}-OH;AKOS025289506;ZINC150339394;CF-1353;AK170271;Fmoc-Asn(Trt)-Ser[Psi(Me,Me)Pro]-OH
Fmoc-Asn(Trt)-Ser(Psi(Me,Me)pro)-OH is an Fmoc-protected asparagine-serine peptide building block bearing orthogonal side-chain protection strategies that support solid-phase peptide synthesis and late-stage functionalization. The molecule contains an Fmoc carbamate on the amino terminus, a side-chain amide from Asn protected as Trt (trityl), and a serine side chain converted into a Psi(Me,Me)pro motif that functions as a protected hydroxyl surrogate with defined steric and electronic properties. The stereochemical integrity of the amino acid framework is maintained at the chiral centers, enabling stereochemically controlled peptide coupling and minimizing epimerization during assembly. The presence of protected amide/amine functionality and a masked serine-derived oxygen allows controlled deprotection and downstream transformations into peptide analogs, biochemical probes, or process-ready intermediates.
1. Protected Peptide Synthesis
Fmoc-Asn(Trt)-Ser(Psi(Me,Me)pro)-OH supports protected amino acid synthesis workflows where orthogonal protecting groups are required for sequential coupling and selective deprotection. The Fmoc group enables base-labile removal to expose the N-terminus for iterative peptide bond formation, while the Trt-protected Asn side-chain amide nitrogen remains protected under standard coupling conditions. The Ser(Psi(Me,Me)pro) side-chain modification provides a stable, protected oxygen functionality that can be carried through peptide assembly and converted during deprotection or derivatization steps to generate defined peptide analogs. The resulting building block is suitable for constructing peptides and peptidomimetics that require controlled side-chain chemistry and stereochemical fidelity across the asparagine-serine segment.
2. Chemical Biology Probes
Fmoc-Asn(Trt)-Ser(Psi(Me,Me)pro)-OH can be applied in chemical biology research to prepare peptide-based probes that incorporate a protected serine-derived oxygen handle for later conjugation or functional group unveiling. The Asn(Trt) side-chain protection helps preserve amide integrity during synthesis, supporting consistent molecular recognition in binding assays or cellular labeling workflows that depend on intact Asn functionality. The Psi(Me,Me)pro-protected serine motif can be designed to undergo controlled transformation into a reactive hydroxyl or related functionality, enabling downstream attachment of fluorophores, affinity tags, or linkers under conditions compatible with other peptide features. The Fmoc strategy further supports scalable synthesis of probe libraries for structure-activity relationship studies and mechanistic investigations using defined stereochemistry.
3. Peptidomimetic And SAR Studies
Fmoc-Asn(Trt)-Ser(Psi(Me,Me)pro)-OH is suitable for peptidomimetic construction where side-chain protection and masked functionality are used to tune conformational behavior and chemical reactivity for SAR studies. The asparagine backbone provides an amide-bearing side chain that can participate in hydrogen-bonding networks, while the Trt protection enables synthetic handling without premature side-chain activation. The Ser(Psi(Me,Me)pro) group introduces a sterically defined, protected oxygen surrogate that can modulate polarity and reactivity patterns across analog series, supporting systematic variation of peptide-like scaffolds. The orthogonal protection set is compatible with iterative analog generation, enabling preparation of closely related derivatives for comparing structure-function outcomes in biochemical assays and molecular modeling-guided design.
4. Bioconjugation And Linker Installation
Fmoc-Asn(Trt)-Ser(Psi(Me,Me)pro)-OH can serve as a precursor for bioconjugation chemistry where peptide fragments are synthesized with protected functional groups that can be activated at a controlled stage. The Fmoc-protected N-terminus supports clean assembly of conjugatable peptide domains, while the Asn(Trt) protection helps maintain side-chain amide stability until deprotection conditions are applied. The Psi(Me,Me)pro serine-derived oxygen masking can be leveraged to regulate timing of functional group exposure, allowing installation of linkers or handles for coupling to proteins, polymers, or nanoparticles after peptide assembly. Downstream derivatives can include site-defined conjugates with preserved stereochemistry and controlled functional density, supporting reproducible biomolecule modification in research and specialty manufacturing contexts.
5. Process Chemistry Intermediate Preparation
Fmoc-Asn(Trt)-Ser(Psi(Me,Me)pro)-OH is applicable as a chiral, protected amino acid intermediate for process chemistry intermediate preparation where orthogonality supports robust manufacturing routes. The Fmoc carbamate and Trt-protected Asn side chain provide chemically distinct deprotection windows, which can be exploited to design stepwise synthesis of longer protected sequences or to generate defined intermediates for further derivatization. The Ser(Psi(Me,Me)pro) motif provides a protected functional group that can reduce undesired side reactions during coupling and purification steps, supporting controlled downstream conversion to target peptide analogs. The resulting intermediate is aligned with fine chemical synthesis practices that require stereochemically consistent building blocks for scale-up-oriented peptide construction and regulated intermediate generation.
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