Z-Ala-ser-OH is a protected dipeptide featuring a benzyloxycarbonyl group that stabilizes the N-terminus and modulates synthetic reactivity. Researchers employ it to explore hydrogen bonding, β-turn formation, and cleavage specificity. The sequence supports modeling of peptide-linker interactions. Its structure is compatible with standard coupling techniques.
CAT No: R2311
CAS No:41864-10-2
Synonyms/Alias:Z-ALA-SER-OH;41864-10-2;(2S)-3-hydroxy-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoic acid;((Benzyloxy)carbonyl)-l-alanyl-l-serine;benzyloxycarbonylalanylserine;CHEMBL3596434;FA111446;CS-0266942;EN300-12580570;(S)-2-((S)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoic acid;(2S)-2-[(2S)-2-{[(BENZYLOXY)CARBONYL]AMINO}PROPANAMIDO]-3-HYDROXYPROPANOIC ACID;
Z-Ala-ser-OH, also known as N-Carbobenzyloxy-L-alanyl-L-serine, is a synthetic dipeptide featuring an N-terminal benzyloxycarbonyl (Z or Cbz) protecting group. As a peptide compound, it serves as a versatile intermediate in peptide chemistry, offering both structural specificity and functional utility for research applications. The presence of the Z-protecting group on the alpha-amino terminus of the alanine residue allows for selective manipulations during peptide synthesis, while the free carboxyl group on the serine residue ensures compatibility with a wide range of coupling strategies. Its defined sequence and protected status make it a valuable tool in the assembly, modification, and study of peptides, particularly in the context of structure-activity relationships and enzymatic processing.
Peptide Synthesis: Z-Ala-ser-OH is widely employed as a building block in solid-phase and solution-phase peptide synthesis. The Z-protecting group safeguards the alpha-amino function of the alanine residue, permitting selective activation and elongation of peptide chains without undesired side reactions. Researchers utilize this dipeptide to introduce defined Ala-Ser motifs into longer peptide sequences, enabling precise control over sequence composition during the stepwise assembly of bioactive peptides, enzyme substrates, or synthetic analogs.
Enzymatic Substrate Studies: The compound serves as a model substrate in enzymology, particularly for studies of proteases and peptidases that recognize or cleave Ala-Ser dipeptide bonds. Its protected N-terminus and free C-terminus enable researchers to investigate enzyme specificity, cleavage kinetics, and mechanism of action in a controlled setting. Such studies provide valuable insights into substrate recognition, active site preferences, and potential inhibitor design for proteolytic enzymes.
Peptide Modification Research: Z-Ala-ser-OH is frequently used in investigations requiring post-synthetic modifications of peptides. The presence of the benzyloxycarbonyl group allows for orthogonal deprotection strategies, facilitating the selective removal of protecting groups under mild conditions. This feature is particularly advantageous in the synthesis of complex peptides where sequential deprotection and functionalization steps are necessary to generate modified peptides with tailored properties for biochemical assays or structural studies.
Structure-Activity Relationship Analysis: The defined sequence and protecting group configuration of this dipeptide make it an ideal candidate for structure-activity relationship (SAR) studies. By incorporating Z-Ala-ser-OH into peptide libraries or analog series, researchers can systematically probe the influence of the Ala-Ser motif on biological activity, receptor binding, or conformational stability. Such SAR analyses are essential for optimizing peptide-based probes, enzyme substrates, or lead compounds in early-stage research and development.
Analytical Method Development: In addition to its synthetic and biochemical roles, Z-Ala-ser-OH is utilized as a calibration standard or reference compound in analytical method development for peptide analysis. Its well-characterized structure and predictable chromatographic behavior make it suitable for validating separation techniques such as HPLC or capillary electrophoresis, as well as for optimizing detection parameters in mass spectrometry-based peptide profiling. These applications support reliable quantitation and quality assessment in peptide research workflows.
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