Ac-Val-NHMe contains a valine-derived amino acid framework in which the α-amino group is converted to an N-methylamide (-NHMe) and the α-carboxyl group is acylated as an acetyl (Ac) amide, yielding a peptide-related amino acid derivative rather than a free amino acid. The side chain corresponds to valine's isopropyl group, and the molecule presents amide-linked carbonyl functionality that can participate in hydrogen-bonding and conformational effects typical of N-acylated amino acid amides while lacking a free carboxyl group and free amino group. Ac-Val-NHMe is used as a defined building block or substrate analogue in peptide chemistry and chemical biology workflows that require a valine-containing, amide-terminated residue for structure-activity studies, analytical method development, or the preparation of more complex peptide derivatives.
CAT No: CP26602
CAS No:19701-84-9
Synonyms/Alias:19701-84-9;Ac-Val-NHMe;Acetyl-L-valinemethylamide;CTK8F7548;ZINC2560845;AKOS006274980;I14-33915
Ac-Val-NHMe is an N-acetylated valine amide (Ac-Val-NHMe), a short, protected valine derivative where the amino terminus is capped with an acetyl group and the carboxyl functionality is converted to a methyl amide. This structure provides a neutral, amide-based valine surrogate that is commonly used as a defined peptide fragment model for studying amide-containing systems and for preparing standardized building blocks in peptide and peptidomimetic workflows. Because it is pre-functionalized as an amide rather than a free amino acid, Ac-Val-NHMe is frequently selected when downstream chemistry requires a stable, non-zwitterionic valine unit with reduced handling complexity.
1. Peptide Fragment Modeling
Ac-Val-NHMe is used as a chemically defined valine-containing peptide fragment model in peptide chemistry and chemical biology, where researchers need a small, amide-stabilized unit that mimics the local backbone environment of valine residues. This makes it useful for method development and comparative studies involving amide-rich substrates, including evaluation of coupling/fragment assembly strategies at the level of defined oligomer segments. Its N-acetyl and carboxamide (NHMe) capping also helps standardize reactivity and minimize variability associated with free termini during analytical characterization of peptide-like intermediates.
2. Peptidomimetic Intermediate Building Block
Ac-Val-NHMe serves as a practical intermediate building block for constructing peptidomimetics and other valine-derived amide architectures in medicinal chemistry and specialty chemical synthesis. By providing a pre-formed valine amide motif, it supports the preparation of larger, well-defined fragments where the valine side chain (isopropyl) is retained while the backbone termini are controlled by the acetyl and methyl amide caps. Teams developing SAR-focused libraries often use such fragments to assemble candidate scaffolds with consistent stereochemical and functional-group presentation, reducing ambiguity that can arise when starting from free amino acids or differently protected analogs.
3. Analytical Reference Substrate
Ac-Val-NHMe is frequently employed as an analytical reference substrate or standard component in studies that monitor reactions involving amide-containing peptide fragments, such as chromatographic method development and qualification of analytical workflows for peptide-like compounds. The capped, neutral nature of Ac-Val-NHMe supports reliable handling and reproducible detection in LC-based assays where defined small molecules are preferred over free amino acids. In practice, researchers use it to benchmark retention behavior, fragmentation patterns, and quantitation performance when validating analytical procedures for valine-containing amide motifs.
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