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 N-Benzyloxycarbonyl-L-asparaginyl-glycine, is a synthetic dipeptide featuring a protected N-terminus. This compound is valued in peptide chemistry for its stability and versatility, making it a crucial building block in the synthesis of more complex peptide sequences. Its unique structure, featuring the Z (benzyloxycarbonyl) protecting group, allows for selective reactions during stepwise peptide assembly, thus facilitating the creation of tailored peptide chains for various research and development purposes. The presence of both asparagine and glycine residues contributes to its biochemical compatibility and adaptability within diverse synthetic protocols.
Peptide Synthesis: Z-Asn-Gly-OH is extensively utilized as a protected dipeptide in solid-phase and solution-phase peptide synthesis. Its benzyloxycarbonyl (Z) group serves as a temporary protecting group for the amino terminus, enabling selective deprotection and coupling reactions without interfering with other functional groups. This property makes it instrumental in the stepwise construction of longer peptide chains, particularly when synthesizing sequences that require asparagine at specific positions. Researchers often incorporate this dipeptide to streamline peptide assembly, reduce side reactions, and improve overall yield in the synthesis of custom peptides for biochemical studies.
Enzyme Substrate Studies: The dipeptide Z-Asn-Gly-OH is frequently employed as a model substrate for investigating the specificity and mechanism of proteolytic enzymes, such as asparaginases and peptidases. Its defined structure allows for precise evaluation of enzyme-substrate interactions, particularly in studies focused on substrate recognition and cleavage kinetics. By using this compound in enzymatic assays, scientists can better understand the catalytic preferences of various enzymes, which is essential for elucidating biological processes and developing enzyme inhibitors for research applications.
Pharmaceutical Research: In drug discovery and pharmaceutical research, N-Benzyloxycarbonyl-L-asparaginyl-glycine serves as a valuable intermediate for the development of peptide-based therapeutics and peptidomimetics. Its protected form allows medicinal chemists to introduce the Asn-Gly motif into larger bioactive molecules without premature side-chain reactions. This capability is particularly important when designing compounds that mimic natural bioactive peptides or when optimizing lead compounds for improved pharmacological properties. The use of this dipeptide intermediate can facilitate the rapid generation of peptide analogs, accelerating the early stages of pharmaceutical development.
Structural Biology: Z-Asn-Gly-OH is also applied in structural biology research, where it aids in the synthesis of peptide fragments used for structural and conformational studies. By incorporating this dipeptide into larger peptide sequences, researchers can investigate the role of asparagine-glycine motifs in protein folding, stability, and intermolecular interactions. Such studies are vital for understanding the structure-function relationships of proteins and for designing peptides with tailored structural attributes for use in biophysical and biochemical assays.
Bioconjugation and Labeling: In the field of bioconjugation, Z-Asn-Gly-OH is employed as a modular unit for the preparation of peptide conjugates and labeled biomolecules. Its protected amino group enables selective functionalization at other positions, which is particularly advantageous when attaching fluorescent tags, affinity labels, or other reporter groups for analytical applications. The resulting conjugates can be used in a variety of experimental setups, including affinity purification, imaging, and detection of specific biomolecular interactions. Through its utility in these diverse application areas, N-Benzyloxycarbonyl-L-asparaginyl-glycine continues to support innovation and precision in peptide-based research and development.
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