N-α-Boc-L-asparagine 4-nitrophenyl ester is a protected amino acid derivative in which L-asparagine is converted to a 4-nitrophenyl ester at the carboxyl group and the α-amino functionality is protected as a Boc (tert-butoxycarbonyl) carbamate. The molecule contains the asparagine side chain with a primary amide, while the Boc group masks the α-amino group and the 4-nitrophenyl ester introduces an aryl leaving group associated with the carboxylate functionality. In peptide chemistry and chemical biology workflows, this protected ester form functions as a stepwise intermediate for controlled acyl transfer and for preparing asparagine-containing peptide derivatives or asparagine-based conjugates bearing a defined electrophilic acyl group.
CAT No: CP00309
CAS No:4587-33-1
Synonyms/Alias:Boc-Asn-ONp;4587-33-1;(S)-4-Nitrophenyl4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate;Boc-L-asparagine4-nitrophenylester;Boc-Asn-OPhNO2;Nalpha-Boc-L-asparagine4-nitrophenylester;PubChem12095;AC1L97SK;15065_ALDRICH;CHEBI:3147;SCHEMBL7417267;15065_FLUKA;MolPort-003-926-624;ZINC1529360;(CH3)3COCONHCH(COOH)CH2COOH;CB-889;AKOS015889942;AM81566;AK161887;N|A-Boc-L-asparagine4-nitrophenylester;N-|A-Boc-L-asparagine4-nitrophenylester;B3915;FT-0623158;LT03329427;ST24036193
N-α-Boc-L-asparagine 4-nitrophenyl ester is an L-asparagine derivative in which the α-amino group is protected as a Boc carbamate and the side-chain carboxamide remains unprotected, while the carboxyl functionality is converted into a 4-nitrophenyl ester. The molecule therefore combines a stereodefined chiral α-center with an activated ester leaving group (4-nitrophenoxy), enabling acyl transfer chemistry under peptide-synthesis-compatible conditions. The presence of the nitro-activated phenyl ester and the Boc-protected nitrogen provides orthogonal reactivity: the ester can participate in coupling or substitution, whereas the Boc group can be removed selectively to reveal an amine for subsequent bond formation. The compound's polar amide side chain and protected α-amino functionality make it a practical chiral intermediate for asparagine-containing peptide building block preparation and for downstream derivatization where controlled acylation is required.
1. Peptide Synthesis
N-α-Boc-L-asparagine 4-nitrophenyl ester supports peptide coupling workflows by serving as an activated asparagine acyl donor in protected amino acid chemistry, where the 4-nitrophenyl ester can undergo nucleophilic acyl substitution to form new amide bonds. The Boc-protected α-amine maintains compatibility with standard peptide assembly strategies by preventing premature amide formation at the α-position, while the intact side-chain carboxamide preserves the asparagine functionality needed for asparagine-specific peptide motifs. The stereochemistry at the α-carbon is retained during acyl transfer, enabling incorporation of L-asparagine residues into peptide chains with defined configuration. Downstream, the resulting peptide intermediates can be used for stepwise elongation, fragment coupling, and protected peptide analog construction in both research-grade synthesis and fine chemical manufacturing.
2. Protected Amino Acid Derivatization
N-α-Boc-L-asparagine 4-nitrophenyl ester is suitable for amino acid derivatization routes that require orthogonal protection and controlled functional group activation, leveraging the Boc carbamate and the activated 4-nitrophenyl ester. The Boc group provides a stable N-protection handle for selective deprotection, while the ester form enables conversion into alternative acyl derivatives without altering the L-asparagine side-chain amide. The nitrophenyl leaving group can facilitate formation of amide-linked intermediates used to generate protected asparagine derivatives, including alternative ester or amide variants for subsequent coupling chemistry. Resulting derivatives can function as process chemistry intermediates for peptide building block preparation, enabling scalable access to asparagine-containing structures used in synthetic methodology development and applied peptide science.
3. Chemical Biology Labeling
N-α-Boc-L-asparagine 4-nitrophenyl ester can be applied in chemical biology research where acylation chemistry is used to install asparagine-derived linkages onto biomolecule scaffolds or affinity handles. The activated ester enables formation of amide bonds with nucleophilic partners such as amino-functional surfaces or linker-bearing amines, while the side-chain carboxamide can participate in hydrogen-bonding interactions that are relevant for molecular recognition and stable conjugate formation. Boc protection helps manage chemoselectivity during conjugation steps by keeping the α-amino functionality masked until intentional deprotection and subsequent coupling. Downstream conjugates and labeled intermediates can be used to probe peptide-protein interactions, map binding determinants in asparagine-rich motifs, and generate chemically defined standards for biochemical assay development.
4. SAR Studies Peptidomimetics
N-α-Boc-L-asparagine 4-nitrophenyl ester serves as a chiral precursor for peptidomimetic and SAR-focused scaffold construction that retains the asparagine side-chain amide while enabling controlled introduction of acyl linkages. The combination of a stereodefined α-center and a protected α-amino group supports assembly of analog series where the asparagine residue is maintained as a key hydrogen-bonding element, while the activated ester supports rapid diversification at the acylation site. Boc deprotection strategies can expose the amine for orthogonal coupling to diverse fragments, supporting parallel synthesis of structure-activity relationship libraries. Resulting analogs and intermediate fragments can be used to generate defined peptide mimetics for SAR studies, enabling systematic evaluation of how asparagine positioning and amide connectivity influence molecular properties.
5. Pharmaceutical Manufacturing Intermediates
N-α-Boc-L-asparagine 4-nitrophenyl ester can be employed in pharmaceutical manufacturing and industrial fine chemical synthesis contexts as a protected amino acid intermediate for producing asparagine-containing peptide intermediates under controlled protection schemes. The Boc carbamate and activated 4-nitrophenyl ester provide a practical handle set for designing manufacturing routes that balance stability during storage and controlled reactivity during coupling or acyl transfer operations. The presence of the side-chain carboxamide supports downstream formation of asparagine residues in peptide fragments used for active pharmaceutical ingredient synthesis or for manufacturing of peptide-based intermediates. Industrial relevance is further supported by the compound's role in enabling chemoselective bond formation steps that integrate with protected amino acid synthesis and scalable peptide assembly logic.
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