Boc-D-Gln(Xan)-OH is a Boc-protected derivative of D-glutamine bearing a xanthyl (Xan) substituent on the side chain, placing it within the class of protected, non-native glutamine analogues used for peptide-related synthesis. The molecule contains a tert-butoxycarbonyl (Boc) protecting group on the amino functional group while the carboxyl group is present as a free acid, and the side chain incorporates the Xan substituent to modify polarity and provide a distinct aromatic functionality relative to unmodified glutamine. In synthesis and chemical biology workflows, this protected amino acid is employed as a building block for incorporating the Xan-modified glutamine motif into peptides or peptide intermediates and for preparing structured conjugation and labeling targets where the side-chain aromatic handle is used for downstream derivatization or analytical characterization.
CAT No: CP26119
CAS No:99092-88-3
Synonyms/Alias:Boc-D-Gln(Xan)-OH;99092-88-3;AmbotzBAA1180;MolPort-008-267-392;ZINC2517114;6945AC;AJ-37026;AK-88935;AB0178395;ST24046211
Chemical Name:N-alpha-t-Butyloxycarbonyl-N-gamma-xantyl-D-glutamine
Boc-D-Gln(Xan)-OH is a Boc-protected D-configured glutamine derivative bearing an "Xan" side-chain functionality, supplied as a protected amino acid building block for downstream peptide assembly and specialized glutamine-site chemistry. The Boc group provides an N-terminal protection handle compatible with standard protected-amino-acid workflows, while the D stereochemistry supports stereochemically defined peptide or peptidomimetic designs. This product is typically selected when a glutamine residue with a defined side-chain modification is required for structure-activity studies, sequence-specific analog generation, or controlled chemical reactivity within a larger synthetic sequence.
1. Modified Peptide Building Blocks
Boc-D-Gln(Xan)-OH is used by peptide synthesis groups to introduce a glutamine position with a defined side-chain modification into peptides and peptidomimetics. Researchers preparing sequence-defined analogs for SAR (structure-activity relationship) studies often choose this type of protected, stereochemically defined glutamine derivative to control how the side chain participates in subsequent steps, including side-chain functional conversion during or after assembly. The Boc-protection pattern supports routine coupling workflows used in protected-amino-acid peptide manufacturing, enabling incorporation as a single-residue segment within longer sequences where the D configuration and side-chain "Xan" functionality are specifically required.
2. Peptidomimetic SAR Development
Boc-D-Gln(Xan)-OH is commonly applied in medicinal chemistry and chemical biology programs that build peptidomimetic libraries to probe how glutamine-like side-chain features influence structure, conformation, and chemical behavior. Teams developing non-natural or stereochemically tuned peptide analogs use this building block to maintain a consistent residue identity across analog series while varying other positions in the peptide scaffold. By selecting a D-glutamine derivative with a side-chain "Xan" modification, developers can align the analog design with the intended chemical logic of the series, supporting downstream evaluation workflows such as analog synthesis, purification, and characterization.
3. Pharmaceutical Intermediate Synthesis
Boc-D-Gln(Xan)-OH is also used as a protected amino acid intermediate in the preparation of more complex, glutamine-derived chemical entities for pharmaceutical intermediate development. Process and R&D chemists employ this reagent when the protected amino acid framework and side-chain functionality must be carried forward into subsequent synthetic stages without premature loss of protection or uncontrolled side reactions. The Boc-protected form supports integration into multi-step routes where the glutamine-derived fragment is a key structural element, including the generation of advanced intermediates used for further functionalization and final assembly into target scaffolds.
4. Stereodefined Analog Production
Boc-D-Gln(Xan)-OH supports stereodefined production of glutamine analogs where D-configuration is required to match a specific design hypothesis or to reproduce a reported stereochemical motif. Chemical biology and peptide engineering workflows often rely on stereochemically controlled building blocks to ensure that analogs differ only in the intended structural variables. In this context, the combination of Boc N-protection and the "Xan" side-chain functionality helps maintain residue integrity during peptide assembly and subsequent downstream handling, enabling consistent batch-to-batch synthesis of stereochemically characterized analogs for analytical comparison and method development.
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