N-((Phenylmethoxy)carbonyl)-L-leucyl-L-leucine is a hydrophobic dipeptide featuring Cbz protection that stabilizes the N-terminus. The residue pairing encourages β-sheet-like tendencies and promotes hydrophobic packing. Researchers use it to study aggregation behavior, enzymatic recognition, and structural transitions. Its protection provides synthetic control.
CAT No: R2271
CAS No:7801-71-0
Synonyms/Alias:Z-LEU-LEU-OH;7801-71-0;(S)-2-((S)-2-(((Benzyloxy)carbonyl)amino)-4-methylpentanamido)-4-methylpentanoic acid;CHEMBL203568;(2S)-4-methyl-2-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]pentanoic acid;N-((Phenylmethoxy)carbonyl)-L-leucyl-L-leucine;N-[(Phenylmethoxy)carbonyl]-L-leucyl-L-leucine;MFCD00038296;N-Cbz-L-Leu-L-Leu-OH;N-Cbz-L-leucinyl-L-leucine;SCHEMBL4872585;BDBM50179750;AKOS016014308;N-Benzyloxycarbonyl-L-leucyl-L-leucine;AS-56436;NS00046929;G77533;(S)-2-((S)-2-(benzyloxycarbonyl)-4-methylpentanamido)-4-methylpentanoic acid;(S)-2-((S)-2-(benzyloxycarbonylamino)-4-methylpentanamido)-4-methylpentanoic acid;
N-((Phenylmethoxy)carbonyl)-L-leucyl-L-leucine is a synthetic peptide derivative composed of two L-leucine residues protected by a phenylmethoxycarbonyl (Cbz or Z) group at the N-terminus. As a dipeptide with a carbobenzoxy-protecting group, it serves as a valuable tool in peptide chemistry, protease research, and biochemical assay development. The structural features of this compound make it particularly relevant for studies involving peptide bond formation, enzymatic hydrolysis, and the design of peptide-based inhibitors or substrates. Its defined sequence and protecting group configuration provide a versatile platform for applications in both academic and industrial research settings.
Peptide synthesis: In solid-phase and solution-phase peptide synthesis, N-((Phenylmethoxy)carbonyl)-L-leucyl-L-leucine is frequently employed as a building block or intermediate. The presence of the Cbz group at the N-terminus allows for selective deprotection under mild conditions, enabling sequential elongation of peptide chains. This compound is particularly useful when incorporating hydrophobic residues in synthetic peptides, as the leucine side chains contribute to the overall stability and folding of the final product. Its use streamlines the assembly of complex oligopeptides and facilitates the development of custom peptide libraries for structure-activity relationship studies.
Enzyme substrate studies: As a dipeptide substrate, the compound is instrumental in investigating the specificity and catalytic mechanisms of proteases, particularly those that recognize leucine-rich sequences. Researchers utilize it to assess the cleavage activity of enzymes such as leucine aminopeptidases and other serine or metalloproteases. By monitoring the hydrolysis of this dipeptide, insights can be gained into enzyme kinetics, substrate recognition, and inhibitor screening, supporting the discovery of novel modulators of proteolytic activity.
Inhibitor development: The structural motif of N-((Phenylmethoxy)carbonyl)-L-leucyl-L-leucine provides a scaffold for the rational design of peptidomimetic inhibitors. Its protected dipeptide format can be modified to enhance binding affinity and selectivity toward target enzymes. Researchers exploit its backbone and side chain properties to generate analogs with improved stability or altered functional groups, supporting the development of potent enzyme inhibitors for biochemical assays and mechanistic studies.
Analytical standards: The defined chemical composition and sequence of this dipeptide make it suitable as an analytical standard in chromatographic and mass spectrometric methods. Laboratories employ it to calibrate instruments, validate peptide quantification protocols, and optimize separation techniques for hydrophobic peptides. Its consistent physicochemical properties provide a reliable reference point for method development and quality control in peptide analysis workflows.
Peptide structure-function analysis: The repetitive leucine motif within N-((Phenylmethoxy)carbonyl)-L-leucyl-L-leucine is of interest in studies exploring the influence of hydrophobic residues on peptide conformation, aggregation, and interaction with biological membranes. By incorporating this dipeptide into model systems, researchers can probe the effects of leucine-rich sequences on peptide folding dynamics, self-assembly, and functional performance in biomimetic environments. These investigations contribute to a deeper understanding of sequence-structure relationships in peptide science.
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