Ac-Leu-NHMe is an N-acetylated leucine amide derivative in which the leucine side chain (isobutyl group) remains intact while the amino acid backbone is converted to an amide, classifying the molecule as a peptide-like amino acid derivative rather than a free amino acid. The structure contains an acetyl (Ac) group at the nitrogen, a terminal N-methylamide (NHMe) at the carboxyl-derived position, and the characteristic α-carbon bearing the side-chain substituent, with stereochemistry not specified in the provided name. Ac-Leu-NHMe is used as a defined building block or model substrate for studying amide-forming/amide-stability behavior in peptide-related chemistry, supporting synthesis planning for leucine-containing fragments and analytical method development involving amino acid amide motifs.
CAT No: CP26999
CAS No:32483-15-1
Synonyms/Alias:Ac-leu-nhme;32483-15-1;Acetyl-L-leucinemethylamide;N-Acetyl-L-Leu-NHMe;AC1OCUU8;SCHEMBL14198796;CTK8F7541;ZINC399562;6096AH;AKOS006272049;KB-47131;(2S)-2-acetamido-N,4-dimethylpentanamide;FT-0693691
Ac-Leu-NHMe is an N-acetylated leucine derivative featuring a C-terminal N-methylamide (NHMe), providing a neutral, peptide-like amide functionality that is commonly used to model or cap the leucine residue in small peptides. With the L-leucine side chain (isobutyl) retained, this compound is frequently handled as a defined building block for structure-property studies, conformational benchmarking, and method development where a protected, non-hydrolyzable terminal amide is advantageous. Its blocked termini reduce competing reactivity relative to free amino acids, making it a practical reagent for downstream peptide and peptidomimetic workflows that require a specific leucine environment.
1. Peptide Fragment Modeling
Ac-Leu-NHMe is used as a defined leucine-containing fragment for peptide fragment modeling in chemical biology and peptide chemistry, particularly when researchers want to study local backbone effects without introducing free N- or C-termini. By presenting an N-acetyl group and a C-terminal N-methylamide, the compound helps standardize hydrogen-bonding patterns and terminal charge states in small-molecule or short-peptide analogs. This makes it useful for benchmarking synthesis strategies, comparing conformational preferences across leucine variants, and generating consistent reference materials for analytical characterization such as LC-MS and NMR.
2. Peptidomimetic Intermediate Development
Ac-Leu-NHMe serves as a practical intermediate building block in peptidomimetic development where leucine is incorporated as a stable, capped residue. Medicinal chemistry and process development teams frequently use such capped amino acid derivatives to assemble larger amide-rich scaffolds while minimizing side reactions associated with terminal functional groups. The N-methylamide end is particularly helpful when the target design requires a non-ionizable terminal amide motif that behaves predictably during coupling steps and downstream purification, supporting the preparation of analog libraries and structure-activity relationship (SAR) series that include leucine as a key hydrophobic element.
3. Analytical Standard And Method Checks
Ac-Leu-NHMe is also used as a reference compound for analytical method development and troubleshooting in workflows that monitor peptide-like species. Because it is a well-defined leucine derivative with blocked termini, it can function as a stable standard for verifying retention behavior, ionization response, and fragmentation patterns in LC-MS/MS assays that include amino acid amide motifs. Analytical groups often select this type of compound when they need a consistent, non-degrading benchmark for sample prep checks, instrument qualification, or comparative quantitation of leucine-containing fragments in synthetic reaction monitoring and impurity profiling.
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