Ac-L-Val-OMe contains an acetylated amino group and the amino acid side chain of L-valine attached to a methyl ester carboxylate (OMe), classifying it as an amino acid ester derivative rather than a free amino acid. The molecule bears an N-acetyl (Ac) protecting group on the α-amino functionality and a methyl ester at the α-carboxyl position, which together modulate chemoselectivity by reducing nucleophilicity of the amine and masking the carboxylate as an ester. Ac-L-Val-OMe is used as a protected, esterified valine building block in peptide and amino acid derivative synthesis and as a substrate or reference material in analytical method development where controlled reactivity of the α-functional groups is required.
CAT No: CP25378
CAS No:1492-15-5
Synonyms/Alias:MethylN-acetyl-L-valinate;1492-15-5;Ac-Val-OMe;AmbotzAAA1948;AC1LCVS6;Acetyl-L-valinemethylester;N-Acetyl-L-valinemethylester;SCHEMBL5814139;CHEMBL3278813;CTK8B8575;MolPort-008-267-320;L-Valine,N-acetyl-,methylester;ZINC388906;7437AA;ANW-60734;AKOS006238315;VZ33096;AJ-20778;AK-81096;KB-47148;ZB011705;methyl(2S)-2-acetamido-3-methylbutanoate;TC-149479
Chemical Name:N-alpha-Acetyl-L-valine methyl ester
Ac-L-Val-OMe is an N-acetylated L-valine methyl ester that combines a protected amino terminus with an esterified carboxyl group, making it a compact, stable amino acid derivative for downstream peptide and amide-forming chemistry. The valine side chain is isopropyl-substituted, providing hydrophobic character that is often leveraged in peptide segment design and in building peptide-like intermediates. In research settings, Ac-L-Val-OMe is handled as a functionalized amino acid synthon where the N-acetyl group suppresses undesired reactivity at the amino terminus while the methyl ester provides a defined electrophilic handle for controlled conversion to more advanced coupling partners.
1. Peptide Segment Building
Ac-L-Val-OMe is used as a protected valine building block for constructing short peptide segments and peptide-like intermediates in custom peptide synthesis workflows. By maintaining an N-acetylated amino terminus, the derivative reduces side reactions during coupling and segment assembly, while the methyl ester form supports subsequent transformation to activated carboxyl derivatives or direct incorporation into amide-forming steps as part of controlled sequence construction. Researchers in peptide chemistry and process development commonly select this format when they want a valine residue with minimized amino-group reactivity and a straightforward downstream conversion of the ester functionality.
2. Amide and Ester Derivatization
Ac-L-Val-OMe serves as a convenient starting material for preparing valine-containing amide derivatives and related functionalized intermediates used in medicinal chemistry and peptide-mimetic development. The methyl ester can be converted into carboxylate-based coupling partners or further derivatized to generate defined analogs for structure-property studies, including hydrophobic residue incorporation where valine's isopropyl side chain is a key steric and electronic contributor. Organic synthesis groups and pharmaceutical intermediate teams often use this derivative because it provides a protected backbone nitrogen (acetylated) and a single, well-defined carboxyl functionality for stepwise elaboration.
3. Hydrophobic Residue Analog Synthesis
Ac-L-Val-OMe is frequently employed to generate hydrophobic valine analogs and N-acetylated residue units for studying how side-chain bulk and local hydrophobicity influence peptide conformation and intermolecular interactions. In chemical biology and peptide engineering contexts, this derivative supports the preparation of standardized residue-containing fragments used to compare analog series with controlled backbone protection patterns. The combination of N-acetyl protection and esterification makes it practical for assembling consistent building blocks that can be carried through iterative synthesis and purification steps without exposing a free amino group during early-stage derivatization.
4. Pharmaceutical Intermediate Development
Ac-L-Val-OMe is used in the development of peptide-derived or amino-acid-derived chemical intermediates where a valine residue must be introduced with controlled functional group masking. Process and R&D teams in pharmaceutical intermediate manufacturing value the derivative form because it is a discrete, weighable synthon that can be advanced into downstream coupling reagents or final intermediate structures while maintaining a protected amino terminus. This makes it useful for building blocks destined for further elaboration toward larger, more complex molecules in research-grade synthesis pipelines.
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