Z-Gly-Gly-Phe-OH is a protected tripeptide featuring a benzyloxycarbonyl cap that regulates N-terminal reactivity. Glycine enhances flexibility while phenylalanine provides aromatic stabilization. Researchers employ it in fragment-coupling studies and synthetic intermediate development. Applications include SPPS planning, building-block libraries, and peptidomimetic design.
CAT No: R2373
CAS No:13171-93-2
Synonyms/Alias:Z-Gly-Gly-Phe-OH;13171-93-2;(S)-11-Benzyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid;(2S)-2-[2-(2-{[(BENZYLOXY)CARBONYL]AMINO}ACETAMIDO)ACETAMIDO]-3-PHENYLPROPANOIC ACID;((Benzyloxy)carbonyl)glycylglycyl-L-phenylalanine;MFCD00055796;Z-Gly-Gly-Phe;Cbz-Gly-Gly-L-Phe;SCHEMBL11239042;BDBM36228;PARPWSYTROKYNG-KRWDZBQOSA-N;AKOS022180797;carbobenzoxyglycylglycyl-l-phenylalanine;HY-W090942;AS-56825;FG111472;CS-0134047;E86793;L-Phenylalanine,N-[(phenylmethoxy)carbonyl]glycylglycyl-(9ci);(S)-11-Benzyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oicacid;
Z-Gly-Gly-Phe-OH is a synthetic tripeptide featuring an N-terminal benzyloxycarbonyl (Z or Cbz) protecting group and a free carboxylic acid at the C-terminus. As a protected peptide fragment, it holds significant value in peptide chemistry, serving as a versatile intermediate for the construction of longer peptide chains and facilitating structure-activity investigations. The sequence, composed of glycine-glycine-phenylalanine, is representative of motifs found in various biologically relevant peptides, and the Z-protecting group enhances its stability during synthetic manipulations. Its well-defined structure and chemical properties make it an important tool for researchers engaged in peptide synthesis, enzymology, and biochemical assay development.
Peptide Synthesis: Z-Gly-Gly-Phe-OH is widely utilized as a building block in stepwise solid-phase and solution-phase peptide synthesis. The presence of the Z-protecting group on the N-terminus shields the amino group from unwanted side reactions, allowing for selective activation and coupling at the C-terminus. This feature streamlines the assembly of larger peptides, especially when incorporating the Gly-Gly-Phe motif into complex sequences. By enabling precise elongation of peptide chains, the compound supports the efficient generation of custom peptides for structure-function studies or library construction.
Enzymatic Substrate Studies: The tripeptide serves as a model substrate for investigating the specificity and catalytic mechanisms of proteases and peptidases. Its defined sequence and protected N-terminus allow researchers to examine enzyme-substrate interactions without interference from free amino groups. Enzymologists employ Z-Gly-Gly-Phe-OH to characterize cleavage patterns, determine kinetic parameters, and screen for enzyme inhibitors, thereby advancing understanding of proteolytic processes relevant to both basic and applied research.
Analytical Method Development: Owing to its well-characterized structure, Z-Gly-Gly-Phe-OH is frequently used as a standard or reference compound in the development and validation of analytical techniques such as high-performance liquid chromatography (HPLC) and mass spectrometry (MS). Its predictable chromatographic and spectrometric behavior aids in the calibration of instruments, optimization of separation conditions, and assessment of method sensitivity and reproducibility. This makes it a valuable tool for laboratories engaged in peptide analysis and quality control.
Peptide Modification Research: The protected tripeptide is instrumental in studies aiming to introduce post-synthetic modifications, such as selective deprotection, derivatization, or conjugation with functional groups. Researchers leverage the stability of the Z-group to perform reactions at other positions on the peptide, facilitating the creation of labeled, crosslinked, or otherwise modified peptides. Such modifications are essential for probing peptide structure, dynamics, and interactions in various biochemical contexts.
Structure-Activity Relationship (SAR) Investigations: Z-Gly-Gly-Phe-OH provides a defined scaffold for systematic modification and evaluation of peptide structure-activity relationships. By serving as a precursor for analog synthesis or as a control compound in biological assays, it enables the dissection of sequence and functional group contributions to biological recognition, binding affinity, or enzymatic activity. These insights are crucial for the rational design of novel peptides with tailored properties for research and industrial applications.
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