Z-N-Me-Asp(OtBu)-OH DCHA is a protected aspartate derivative with N-methylation and tert-butyl esterification. These modifications adjust steric profile, backbone rigidity, and coupling selectivity. Researchers use it to generate constrained peptidomimetics and examine methylation effects on structure. Its dual protection supports orthogonal synthesis.
CAT No: R2158
CAS No:200341-08-8
Synonyms/Alias:Z-N-Me-Asp(OtBu)-OH DCHA;42417-70-9;200341-08-8;Dicyclohexylamine (S)-2-(((benzyloxy)carbonyl)(methyl)amino)-4-(tert-butoxy)-4-oxobutanoate;N-cyclohexylcyclohexanamine;(2S)-2-[methyl(phenylmethoxycarbonyl)amino]-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid;MFCD00237355;SCHEMBL248887;VTIXCSIGDUSBDL-ZOWNYOTGSA-N;(2S)-2-{[(benzyloxy)carbonyl](methyl)amino}-4-(tert-butoxy)-4-oxobutanoic acid; N-cyclohexylcyclohexanamine;AS-82795;G78119;S-42417-70-9;Z-N-Methyl-L-aspartic acid beta-t-butyl ester dicyclohexylammonium salt;dicyclohexylamine (S)-2-((benzyloxycarbonyl)(methyl)amino)-4-tert-butoxy-4-oxobutanoate;Dicyclohexylamine(S)-2-(((benzyloxy)carbonyl)(methyl)amino)-4-(tert-butoxy)-4-oxobutanoate;L-Asparticacid,N-methyl-N-[(phenylmethoxy)carbonyl]-,4-(1,1-dimethylethyl)ester;(s)-2-((benzyloxycarbonyl)(methyl)amino)-4-tert-butoxy-4-oxobutanoic acid dicyclohexylammonium salt;
Z-N-Me-Asp(OtBu)-OH DCHA is a synthetically protected derivative of N-methyl aspartic acid, featuring a benzyloxycarbonyl (Z) group at the N-terminus and a tert-butyl ester (OtBu) at the side-chain carboxyl, supplied as the dicyclohexylamine (DCHA) salt. As a specialty amino acid building block, it is engineered to facilitate the incorporation of N-methylated aspartic acid residues into peptides during solid-phase peptide synthesis (SPPS) and solution-phase protocols. The N-methylation and selective protection of both the α-amino and side-chain carboxyl groups enhance its utility in generating conformationally constrained peptides and peptidomimetics, which are of high interest in biochemical and pharmaceutical research. Its unique structural features make it valuable for modulating peptide backbone rigidity, improving metabolic stability, and investigating structure-activity relationships in bioactive peptides.
Peptide synthesis: In the context of peptide chemistry, Z-N-Me-Asp(OtBu)-OH DCHA serves as a crucial building block for the incorporation of N-methyl aspartic acid residues into linear and cyclic peptides. The N-methyl modification imparts significant conformational constraints, which can enhance the proteolytic stability of peptides and influence their secondary structure. The Z and OtBu protecting groups are orthogonally removable, allowing for precise stepwise assembly of complex sequences without undesired side reactions. Researchers utilize this derivative to synthesize peptides with improved pharmacokinetic profiles or to probe the impact of N-methylation on peptide folding and function.
Peptidomimetic design: This protected N-methylated aspartic acid is frequently employed in the design and synthesis of peptidomimetics, which are peptide-like molecules engineered to mimic the biological activity of natural peptides while exhibiting enhanced resistance to enzymatic degradation. The N-methyl group restricts amide bond rotation, thereby stabilizing specific backbone conformations that can be critical for receptor binding or biological activity. By incorporating this building block, chemists can systematically explore the relationship between backbone modification and bioactivity, supporting the rational design of novel molecular probes or lead compounds in early-stage research.
Structure-activity relationship studies: The selective use of Z-N-Me-Asp(OtBu)-OH DCHA enables detailed structure-activity relationship (SAR) investigations, particularly in the context of bioactive peptides and protein-protein interaction modulators. By substituting standard aspartic acid residues with their N-methylated counterparts, researchers can assess the effects on binding affinity, selectivity, and conformational dynamics. Such systematic modifications are instrumental in elucidating the molecular determinants of peptide function, guiding the optimization of sequence motifs for improved biological properties.
Solid-phase peptide synthesis optimization: The chemical stability and solubility profile of this protected amino acid derivative make it highly suitable for automated SPPS workflows. Its compatibility with common coupling reagents and resin systems streamlines the assembly of complex peptide sequences, including those containing multiple N-methylated residues. The DCHA salt form further enhances handling and incorporation efficiency during synthesis, reducing the risk of racemization and minimizing side reactions. This supports the reliable production of high-quality peptides for biochemical and biophysical studies.
Analytical reference and method development: Beyond its role as a synthetic intermediate, Z-N-Me-Asp(OtBu)-OH DCHA is also utilized as a reference standard in analytical method development. Its well-defined structure and predictable chromatographic behavior make it useful for calibrating analytical instruments such as HPLC or LC-MS systems, particularly in laboratories focused on peptide analysis or quality control. By providing a benchmark for retention time and detection sensitivity, it supports the validation of analytical protocols used in peptide research and manufacturing environments.
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