Boc-L-Asn(Xan)-OH is a Boc-protected, L-configured amino acid derivative in which the asparagine side chain is modified to incorporate an Xan substituent, yielding a nonstandard Asn analogue for peptide-related chemistry. The molecule contains a Boc-protected α-amino group and a free carboxylic acid, while the side-chain functionality includes the Xan-bearing substituent that can present distinct hydrogen-bonding or steric features relative to unmodified asparagine. In synthesis, this protected analogue is used as a building block to introduce the Xan-modified asparagine residue into peptides via stepwise coupling strategies, supporting chemoselective handling of the α-amino functionality during assembly and subsequent downstream transformations of the side chain as required by the target structure.
CAT No: CP25970
CAS No:65420-40-8
Synonyms/Alias:Boc-Asn(Xan)-OH;65420-40-8;(S)-4-((9H-Xanthen-9-yl)amino)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoicacid;N-Alpha-t-Boc-N-beta-xanthyl-L-asparagine;N-Boc-N-xanthyl-L-asparagine;AmbotzBAA1070;PubChem18926;MolPort-006-705-562;ACT05117;ZINC2539578;CB-918;AKOS016008669;RL04488;Nalpha-Boc-Nbeta-xanthenyl-L-asparagine;AJ-38898;AK-50011;AN-38639;N941;AB0007163;FT-0629961;ST24020833;Y-8960;N(alpha)-boc-N(gamma)-(9-xanthenyl)-L-asparagine;(2S)-2-(tert-butoxycarbonylamino)-4-oxo-4-(9H-xanthen-9-ylamino)butanoicacid;(2S)-2-[(tert-butoxycarbonyl)amino]-3-[(9H-xanthen-9-yl)carbamoyl]propanoicacid
Chemical Name:N-alpha-t-Butyloxycarbonyl-N-beta-xantyl-L-asparagine
Boc-L-Asn(Xan)-OH is a Boc-protected L-asparagine derivative bearing an asparagine side-chain functional group consistent with a Xanyl (Xan) substituent, making it a specialized protected amino acid building block for peptide and peptidomimetic synthesis. The Boc group provides an N-terminal protection strategy commonly used to control reactivity during stepwise assembly, while the Xanyl side-chain functionality is selected to support downstream incorporation of a tailored Asn side-chain motif. This reagent is typically handled as a research-grade intermediate for controlled sequence construction and for preparing defined peptide analogs used in chemical biology and medicinal chemistry workflows.
1. Solid-Phase Peptide Building
Boc-L-Asn(Xan)-OH is used as an amino acid building block for custom peptide synthesis workflows where an Asn-derived side-chain motif must be introduced with defined protection and functionality. Peptide synthesis teams rely on Boc-protected amino acid derivatives to manage N-terminus reactivity during stepwise assembly, enabling consistent coupling performance and minimizing side reactions that can occur with unprotected amino acids. The presence of the Xanyl-modified side chain supports preparation of peptide sequences or peptidomimetic analogs where the Asn position is required to carry a specific substituent pattern rather than the native amide alone.
2. Peptidomimetic SAR Intermediates
Boc-L-Asn(Xan)-OH is commonly employed in medicinal chemistry programs that generate structure-activity relationship (SAR) libraries containing Asn analogs with a modified side-chain handle. Synthetic chemistry groups use this type of protected amino acid intermediate to access defined peptide-like scaffolds for lead optimization, where maintaining a precise residue identity at the Asn position is critical for comparing analogs. By selecting a side-chain-modified Asn derivative, researchers can tune chemical properties at the residue level while keeping the overall peptide assembly workflow compatible with standard protected amino acid strategies used for library production.
3. Defined Side-Chain Peptide Analog Synthesis
Boc-L-Asn(Xan)-OH supports the preparation of peptide analogs intended for chemical biology studies that require a controlled Asn side-chain environment. Researchers preparing defined peptide standards, reference materials, or sequence-specific probes use protected amino acid derivatives to ensure that the residue is incorporated in a reproducible manner with the intended side-chain functionality preserved through synthesis. This makes Boc-L-Asn(Xan)-OH a practical choice when the downstream experimental design depends on having a specific Asn-derived substituent at a known position within a peptide scaffold, rather than relying on unmodified asparagine.
4. Pharmaceutical Intermediate Development
Boc-L-Asn(Xan)-OH is also used as a protected amino acid intermediate in downstream pharmaceutical intermediate development, particularly where peptide-derived fragments or peptidomimetic intermediates must be assembled with consistent residue-level definition. Process development and custom synthesis teams select Boc-protected amino acid derivatives to streamline the production of well-defined intermediates for further functionalization or coupling steps. The Xanyl-modified Asn side chain provides a structural basis for generating defined building blocks that can be carried into subsequent synthetic stages as part of a controlled, specification-driven development workflow.
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