Fmoc-Gln(Mtt)-OH is an Fmoc-protected glutamine derivative in which the side-chain amide of glutamine is masked as an Mtt (4-methyltrityl) protected amine, yielding a non-free amino acid building block for peptide-related synthesis. The molecule contains an N-terminal Fmoc carbamate and a C-terminal carboxylic acid, while the side-chain functional group is present as an Mtt-protected amide/amine equivalent that controls chemoselectivity during coupling and subsequent deprotection steps. In synthesis, this protected amino acid is employed as a substrate for stepwise peptide assembly, including solid-phase peptide synthesis, where the orthogonal protection pattern supports selective side-chain handling and downstream preparation of glutamine-containing peptide derivatives.
CAT No: CP26390
CAS No:144317-23-7
Synonyms/Alias:Fmoc-Gln(Mtt)-OH;144317-23-7;FMOC-GLN-OH;MolPort-020-004-669;7110AA;ZINC71788107;AK-89808;FT-0686521;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-((diphenyl(p-tolyl)methyl)amino)-5-oxopentanoicacid
Fmoc-Gln(Mtt)-OH is an Fmoc-protected glutamine derivative bearing a side-chain amide protected as an Mtt (methyltrityl) thioether-stabilized protecting group, yielding a protected amino acid building block with two orthogonally addressable nitrogen functionalities. The molecule contains the Fmoc carbamate on the α-amino group for base-labile removal, a free α-carboxylic acid for coupling chemistry, and a stereochemically defined α-chiral center inherited from L-glutamine. The Mtt group on the side-chain amide nitrogen is designed for acid-mediated cleavage while remaining stable under common peptide assembly conditions, enabling controlled exposure of the side-chain for subsequent derivatization. The combination of a bulky trityl-type protecting group and a robust Fmoc handle provides predictable reactivity patterns for peptide synthesis, side-chain functionalization, and downstream intermediate preparation in fine chemical manufacturing.
1. Peptide Synthesis
Fmoc-Gln(Mtt)-OH is used in peptide synthesis workflows where orthogonal protection of the α-amino group and the glutamine side-chain amide is required for stepwise chain assembly. The Fmoc carbamate supports standard peptide coupling at the α-carboxylate, while the Mtt-protected side-chain nitrogen remains masked to prevent undesired side reactions during iterative N-terminal deprotection and coupling cycles. Acid-triggered removal of the Mtt group can be applied after chain elongation to generate a reactive side-chain amide for further modification or for incorporation into longer peptide frameworks. The resulting glutamine-containing peptide products and protected intermediates can be directed toward sequence-specific studies and peptide analog generation, aligning with peptide chemistry needs for controlled functional group exposure.
2. Side-Chain Functionalization
Fmoc-Gln(Mtt)-OH serves as a controlled precursor for side-chain functionalization strategies that target the glutamine amide after selective deprotection. The protected side-chain nitrogen enables introduction of post-assembly modifications such as derivatization into amide-linked motifs, conversion to alternative nitrogen-containing handles, or attachment of solubilizing and recognition elements while minimizing cross-reactivity during earlier synthetic steps. The orthogonal protection pattern supports a workflow in which peptide coupling proceeds with the side-chain masked, followed by Mtt removal to expose the side-chain amide for targeted transformation. Downstream products include functionalized peptide fragments and amino acid derivatives used in chemical biology research, peptidomimetic construction, and scaffold diversification for structure-activity relationship studies.
3. Chemical Biology Probes
Fmoc-Gln(Mtt)-OH can be applied in chemical biology research to prepare glutamine-containing labeling probes and molecular tools that require controlled side-chain availability for conjugation chemistry. The molecule's α-carboxylic acid and Fmoc-protected amine facilitate incorporation into peptide-based reporters, while the Mtt-protected side-chain amide allows timed generation of a reactive nitrogen site for subsequent coupling to linkers, affinity tags, or reporter groups. The stereodefined glutamine backbone supports incorporation into peptide scaffolds that mimic native amide recognition patterns, enabling reliable placement of functional groups for biochemical investigations. The orthogonal deprotection logic supports downstream synthesis of probe libraries and conjugation-ready intermediates used for studying binding interfaces, protein interactions, and substrate recognition behavior.
4. Peptidomimetics And SAR
Fmoc-Gln(Mtt)-OH is suitable for peptidomimetic construction and SAR-oriented library synthesis where glutamine side-chain chemistry must be introduced with controlled protection. The Fmoc handle enables reliable incorporation into short peptide segments or constrained analogs, while the Mtt-protected side-chain amide supports later conversion into alternative functional groups that tune hydrogen-bonding capacity, polarity, and conformational preferences. Selective side-chain unmasking supports generation of analogs that can be systematically compared in structure-activity relationship studies using consistent backbone placement and stereochemical fidelity. The compound thus functions as a chiral amino acid intermediate for building nitrogen-rich motifs in medicinal chemistry and applied peptide science.
5. Pharmaceutical Intermediate Preparation
Fmoc-Gln(Mtt)-OH can be used in pharmaceutical intermediate preparation for manufacturing routes that require protected amino acid building blocks with orthogonal deprotection behavior. The Fmoc-protected α-amino group and acid-stable carboxylic acid functionality enable scalable peptide coupling steps under controlled conditions, while the Mtt side-chain protection supports selective unveiling of the glutamine amide during later stages of synthesis. The predictable reactivity profile supports downstream conversion into drug substance-related peptide fragments, process intermediates, and protected precursors for further functional group transformations. Industrial relevance arises from the compound's compatibility with protected amino acid chemistry strategies that reduce side reactions and enable controlled synthesis planning in fine chemical production and pharmaceutical manufacturing contexts.
6. Process Chemistry And Specialty Synthesis
Fmoc-Gln(Mtt)-OH is applicable to process chemistry and specialty chemical production where orthogonally protected amino acid derivatives are required for robust, reproducible synthetic sequences. The presence of an Fmoc carbamate and an Mtt-protected side-chain amide provides a two-stage functional group management scheme that can be aligned with manufacturing timelines, including N-terminal deprotection during assembly and later side-chain unmasking for controlled derivatization. The chiral amino acid intermediate form supports stereochemically consistent downstream products, including protected glutamine-containing intermediates for peptide and peptidomimetic manufacturing. The compound therefore supports industrially relevant amino acid derivatization workflows that depend on selective protection and deprotection to generate defined functionalized molecules for applied research and production-scale synthesis.
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