N-α-Z-L-asparagine ethyl ester is a protected amino acid derivative in which the asparagine side chain contains a carboxamide functionality and the α-amino group is carbobenzoxy (Z) protected, with the α-carboxyl group present as an ethyl ester. The molecule therefore bears a Z-protected amine, a side-chain amide, and an esterified carboxyl group, and it is specified as the L stereochemical form at the α-carbon. In peptide and amino-acid chemistry workflows, this structure functions as a protected, esterified asparagine building block that can be used in stepwise synthesis and subsequent transformations that require controlled chemoselectivity of the α-amino group and side-chain carboxamide.
CAT No: CP00326
N-α-Z-L-asparagine ethyl ester is an L-asparagine-derived amino acid ester bearing an N-α benzyloxycarbonyl (Z, Cbz) protecting group and an ethyl ester at the carboxyl terminus. The molecule retains the asparagine side chain amide (-CH2-CONH2), which provides a polar hydrogen-bonding motif for recognition and for subsequent functionalization, while the stereogenic center at the α-carbon is fixed in the L-configuration. The Z group masks the α-amino functionality to support selective peptide coupling at the protected nitrogen, and the ethyl ester can be manipulated under standard amino acid ester hydrolysis or transesterification conditions to reach a carboxylic acid for amide bond formation. The combination of a protected α-amino group, an esterified C-terminus, and an unprotected side-chain amide makes this compound a practical chiral intermediate for protected amino acid synthesis and downstream peptide building block preparation.
1. Peptide Synthesis
N-α-Z-L-asparagine ethyl ester supports peptide building block workflows in solid-phase or solution-phase peptide synthesis where controlled N-protection and C-terminal activation are required. The Z-protected α-amine enables selective coupling chemistry at the esterified carboxyl side, while the ethyl ester serves as a handle for conversion to the corresponding acid or activated derivative prior to amide bond formation. The side-chain asparagine amide participates in hydrogen-bonding patterns that can influence folding propensity and solubility of peptide intermediates and final constructs. Peptide chemists can incorporate the protected asparagine residue into linear sequences or peptide fragments, then carry out deprotection and further side-chain modifications as needed for sequential assembly and analog generation.
2. Side-Chain Functionalization
N-α-Z-L-asparagine ethyl ester is suitable for chemical biology and medicinal chemistry intermediate preparation focused on asparagine side-chain derivatization. The free side-chain amide can be transformed into protected or functionalized derivatives through acylation, activation, or conversion strategies that preserve the L-stereochemistry at the α-carbon. The Z group and ester functionality allow orthogonal protection planning, enabling selective manipulation of the side-chain without premature interference from the α-amino group. Generated asparagine analogs can be used to probe hydrogen-bonding interactions, tune polarity, or introduce handles for subsequent conjugation, supporting structure-activity relationship studies and peptidomimetic construction.
3. Protected Amino Acid Chemistry
N-α-Z-L-asparagine ethyl ester functions as a chiral protected amino acid intermediate for manufacturing-oriented synthesis of protected asparagine derivatives. The Z protecting group provides stable N-protection during ester handling and intermediate conversions, while the ethyl ester can be adjusted to match downstream coupling requirements for peptide-grade carboxylic acid formation. The retained side-chain amide reduces the need for early side-chain protection in routes where the amide can tolerate coupling and purification conditions. Process chemists can employ this protected amino acid ester as a feedstock for producing N-protected asparagine acids, activated esters, or alternative protected forms used in fine chemical synthesis and peptide building block supply chains.
4. Bioconjugation Chemistry
N-α-Z-L-asparagine ethyl ester can be applied to bioconjugation and biomolecule labeling strategies that rely on controlled functional group presentation. The orthogonally protected α-amino group and ester-derived carboxyl functionality support the construction of peptide-linker segments that incorporate an asparagine motif for hydrogen-bonding-driven positioning. The side-chain amide can serve as a site for controlled derivatization to introduce conjugation-ready moieties while maintaining the stereochemical integrity of the amino acid residue. Downstream conjugate synthesis can leverage the protected amino acid scaffold to generate defined peptide conjugates, affinity probes, or labeling reagents used in biochemical research workflows.
5. Analytical Standards
N-α-Z-L-asparagine ethyl ester is appropriate for analytical method development and reference material preparation in amino acid and peptide characterization. The combination of Z protection and an ethyl ester creates a distinguishable chemical signature that can support LC-MS or chromatographic identification of asparagine-containing intermediates and protected peptide fragments. The L-configuration and preserved side-chain amide enable consistent behavior when validating derivatization, hydrolysis, or peptide coupling steps used in analytical workflows. Reference compounds derived from this scaffold can be used to monitor reaction progress, confirm stereochemical integrity of asparagine residues, and support quality control of peptide building block preparations in research and industrial settings.
3. C-Peptide replacement therapy and sensory nerve function in type 1 diabetic neuropathy
5. Emerging applications of nanotechnology for diagnosis and therapy of disease: a review
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More