Z-Asn-Gly-OH provides a protected dipeptide that supports controlled coupling steps in synthetic workflows. Asparagine and glycine contribute flexibility and hydrogen-bond capability. Researchers analyze its performance during resin-bound elongation. Applications include peptide synthesis optimization, backbone engineering, and protected-fragment design.
CAT No: R2477
CAS No:56675-97-9
Synonyms/Alias:Z-Asn-Gly-OH;56675-97-9;Cbz-Asn-Gly-OH;2-[[(2S)-4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoyl]amino]acetic acid;MFCD08458674;SCHEMBL6671871;AIVHZBIRKPAQGR-JTQLQIEISA-N;HY-P5008;DA-79074;FA111580;((Benzyloxy)carbonyl)-L-asparaginylglycine;CS-0675656;
Z-Asn-Gly-OH, also known as benzyloxycarbonyl-asparaginyl-glycine, is a synthetic dipeptide featuring a protected N-terminus with a benzyloxycarbonyl (Z) group. This compound is widely utilized in peptide chemistry due to its stability and the functional versatility conferred by its protected structure. As a building block in solid-phase and solution-phase peptide synthesis, Z-Asn-Gly-OH enables precise incorporation of the asparagine-glycine sequence into larger peptide chains. Its relevance extends to various domains of biochemical research, where it supports the development of custom peptides for mechanistic and structural studies.
Peptide Synthesis: Z-Asn-Gly-OH is primarily employed as a protected dipeptide fragment in the stepwise assembly of longer peptide sequences. The presence of the Z-group on the N-terminus prevents undesired side reactions during coupling steps, ensuring high fidelity in sequence incorporation. Researchers utilize this compound in both traditional solution-phase and automated solid-phase peptide synthesis workflows, benefitting from its compatibility with standard deprotection and coupling protocols. Its use streamlines the synthesis of peptides containing the asparagine-glycine motif, which is frequently found in biologically active proteins and signaling molecules.
Enzymatic Substrate Studies: The protected dipeptide serves as a valuable substrate or intermediate in enzymatic assays focused on protease specificity and mechanism elucidation. By incorporating Z-Asn-Gly-OH into substrate libraries, scientists can probe the activity of asparaginyl endopeptidases and related enzymes. The Z-protection not only prevents premature degradation but also facilitates selective cleavage analysis, enabling detailed studies of enzyme-substrate interactions and catalytic preferences.
Peptide Modification Research: In the context of post-synthetic modifications, Z-Asn-Gly-OH offers a controlled platform for introducing chemical alterations at the asparagine or glycine residues. Its protected state allows for selective deprotection and subsequent functionalization, such as glycosylation or isotopic labeling, without interfering with other reactive groups in the peptide. This capability is particularly useful in the design of peptide probes, affinity tags, or modified peptide standards for advanced analytical applications.
Structural Biology: The dipeptide's defined sequence and protected structure make it a suitable model compound for investigating peptide folding, conformational dynamics, and intermolecular interactions. Researchers employ Z-Asn-Gly-OH in studies utilizing techniques such as nuclear magnetic resonance (NMR) spectroscopy and X-ray crystallography to elucidate the influence of N-terminal protection on peptide structure. Insights gained from such investigations inform the rational design of synthetic peptides with tailored structural properties.
Combinatorial Library Construction: Z-Asn-Gly-OH is frequently incorporated into combinatorial peptide libraries used for high-throughput screening of binding motifs and functional sequences. Its stability and compatibility with automated synthesis platforms enable efficient generation of diverse peptide populations containing the asparagine-glycine motif. These libraries facilitate the identification of novel ligands, enzyme substrates, or protein interaction partners, supporting the advancement of peptide-based research and discovery efforts across multiple scientific disciplines.
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