Fmoc-Asn(Mtt)-OH is an Fmoc-protected amino acid derivative based on asparagine, featuring a side-chain amide and an N-terminus masked by the 9H-fluoren-9-ylmethoxycarbonyl (Fmoc) group for controlled peptide coupling. The side-chain amide is further protected as an Mtt (4-methyltrityl) group, while the molecule retains a free carboxylic acid functionality and an amino acid backbone suitable for stepwise assembly. In peptide synthesis and related chemical biology workflows, this protected analogue provides orthogonal protection to manage chemoselectivity during sequential deprotection and coupling, and it can be used to introduce asparagine residues bearing a protected side-chain amide into peptides or peptide-related intermediates.
CAT No: CP26389
CAS No:144317-22-6
Synonyms/Alias:Fmoc-Asn(Mtt)-OH;144317-22-6;6786AH;ZINC71788106;AKOS015909246;I14-33069
Fmoc-Asn(Mtt)-OH is an Fmoc-protected asparagine derivative bearing a side-chain amide and an Mtt (4-methyltrityl) protecting group on the asparagine side-chain nitrogen. The molecule combines an aniline-like aromatic Fmoc carbamate at the alpha-amino position with a masked secondary amide functionality, creating a stable, orthogonally protected amino acid building block for peptide chemistry. The chiral alpha-center is preserved as a single stereochemical handle for stereocontrolled coupling, while the carboxylic acid enables formation of activated esters and direct peptide bond construction under standard amino-acid coupling conditions. The Mtt group provides acid-labile side-chain deprotection behavior that can be used to expose the native asparagine side-chain amide for subsequent derivatization, hydrogen-bonding interactions, and downstream synthetic transformations.
1. Peptide Synthesis
Fmoc-Asn(Mtt)-OH supports stepwise solid-phase or solution-phase peptide synthesis where the Fmoc group governs alpha-amino deprotection and the Mtt group temporally masks the side-chain amide nitrogen. The side-chain amide and carboxylic acid functionality enable incorporation of an asparagine residue with controlled protection-state management during peptide assembly. Orthogonal deprotection strategies can be applied to reveal the side-chain amide at a chosen stage, supporting selective formation of asparagine-containing motifs and maintaining compatibility with common peptide coupling chemistries. The resulting peptides and peptide fragments can be used as research-grade building blocks for mapping sequence effects, studying amide-mediated recognition, and generating defined peptidic scaffolds for further modification.
2. Chemical Biology
Fmoc-Asn(Mtt)-OH can be employed to prepare asparagine-bearing peptide probes and molecular tools that rely on side-chain amide hydrogen-bonding for binding-site mimicry. The protected asparagine side chain allows controlled timing of exposure, enabling sequential labeling workflows where the side-chain functionality is revealed without perturbing the peptide backbone. The Fmoc-protected alpha-amino group facilitates clean incorporation into peptide conjugates used in chemical biology studies, including affinity probes and substrate analogs for biomolecular recognition experiments. Downstream, the deprotected asparagine side chain can participate in site-specific derivatization to generate defined interaction elements for mechanistic studies and structure-function interrogation.
3. Peptidomimetics
Fmoc-Asn(Mtt)-OH serves as a chiral amino acid intermediate for constructing peptidomimetic frameworks that preserve asparagine-like polarity while enabling controlled functional group unveiling. The combination of an Fmoc-protected alpha-amino group and an Mtt-protected side-chain amide supports iterative synthesis of analogs where side-chain chemistry is introduced after backbone assembly. The exposed carboxylic acid can be converted into activated intermediates for coupling to scaffold-forming fragments, while the side-chain amide can be retained or transformed to tune hydrogen-bonding patterns in mimicry designs. Peptidomimetic products derived from this building block can be applied in molecular design efforts that emphasize amide-mediated recognition and stereochemically defined conformational behavior.
4. Protein Engineering
Fmoc-Asn(Mtt)-OH is suitable for preparing asparagine-containing peptide segments used in protein engineering workflows, including defined fragments for binding studies and assembly of sequence-specific constructs. The stereochemically defined alpha-amino center and protected side-chain amide support accurate placement of asparagine in engineered sequences where hydrogen-bonding networks influence folding, stability, or interaction geometry. The orthogonal protection strategy helps manage side-chain reactivity during segment coupling, enabling controlled generation of longer constructs from protected building blocks. Downstream derivatives can be used to generate analytical standards, segment libraries, or engineered peptide/protein fragments that reflect targeted sequence features.
5. Pharmaceutical Manufacturing
Fmoc-Asn(Mtt)-OH can be applied in industrial peptide manufacturing contexts where orthogonally protected amino acid building blocks are required to control side-chain functionality during scalable synthesis. The Fmoc carbamate and Mtt-protected side-chain amide provide a protection scheme compatible with manufacturing-oriented sequence assembly, where deprotection and coupling steps can be orchestrated to yield defined intermediates. The carboxylic acid functionality supports conversion to activated forms for solution-phase coupling or integration into automated synthesis workflows, supporting consistent incorporation of asparagine residues into peptide intermediates. Downstream, the resulting protected or partially deprotected peptide materials can serve as intermediates for further functionalization, purification development, and defined product construction in fine chemical and pharmaceutical intermediate production.
6. Process Chemistry Intermediate
Fmoc-Asn(Mtt)-OH functions as a chiral, orthogonally protected amino acid intermediate for process chemistry routes that require predictable protection-state control and robust coupling compatibility. The Fmoc-protected alpha-amino group can be removed under base-promoted conditions, while the Mtt group provides a distinct deprotection handle for revealing the side-chain amide at a staged point in a synthetic sequence. The presence of both a carboxylic acid and protected amide nitrogen supports conversion to activated derivatives for coupling, as well as controlled downstream transformations that depend on side-chain exposure. The compound can therefore be utilized to prepare defined peptide building block streams, process intermediates for SAR-focused libraries, and manufacturable chiral inputs for specialty chemical production where protection strategy strongly influences impurity profiles and intermediate identity.
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