Ac-L-Met-OMe contains L-methionine in an amino acid derivative form, where the alpha-amino group is acetylated (Ac-) and the carboxyl group is esterified as a methyl ester (OMe), yielding a neutral, protected methionine analogue rather than a free amino acid. The side chain retains the thioether functionality characteristic of methionine, while the molecule bears no free carboxylate or free amino group, which affects its chemoselectivity in peptide coupling and related transformations. Ac-L-Met-OMe is used as a defined methionine-containing building block and substrate in peptide synthesis and in solution- or solid-phase assembly workflows where controlled reactivity of the protected termini is required for preparing methionine-containing peptides and related derivatives.
CAT No: CP25794
CAS No:35671-83-1
Synonyms/Alias:AC-MET-OME;35671-83-1;N-Acetyl-L-methioninemethylester;n-acetylmethioninemethylester;ZINC02390928;Ac-L-Met-OMe;SCHEMBL111170;CCRIS5538;Acetyl-L-methioninemethylester;CTK2H5508;MolPort-008-267-309;YVMKSJIMTATAAS-ZETCQYMHSA-N;ZINC2390928;6103AH;AKOS015908060;L-Methionine,N-acetyl-,methylester;FT-0652911;ST51054196;K-8056;Methyl2-(acetylamino)-4-(methylsulfanyl)butanoate#;2-Acetylamino-4-(methylthio)butyricacid,methylester
Chemical Name:N-alpha-Acetyl-L-methionine methyl ester
Ac-L-Met-OMe is an acetylated L-methionine methyl ester designed for peptide and peptidomimetic chemistry workflows where a protected amino acid derivative is needed to control terminal functionality. The acetylated N-terminus and methyl ester at the carboxyl terminus reduce undesired side reactions during coupling and downstream transformations, while the methionine thioether side chain provides a sulfur-containing handle commonly leveraged in chemical biology and peptide chemistry. This derivative is frequently handled as a defined building block for segment synthesis, reference compound preparation, and controlled reactivity studies involving methionine-containing sequences.
1. Peptide Segment Building
Ac-L-Met-OMe is used as a methionine-containing segment building block in peptide synthesis planning, especially when researchers need a derivative with a masked N-terminus and esterified C-terminus to manage chemoselectivity across multi-step assembly. Peptide chemistry groups and custom peptide manufacturing workflows often select this type of protected amino acid derivative to streamline condensation strategies and to maintain the methionine side chain in a form compatible with standard peptide-workup conditions. In practice, it supports the preparation of defined intermediates for solution-phase or stepwise peptide construction where terminal protection is required for controlled coupling and purification.
2. Peptidomimetic and Analog Synthesis
Ac-L-Met-OMe is commonly incorporated into peptidomimetic and methionine-analog synthesis programs where terminal functional groups must be tuned to match a target scaffold's reactivity profile. Medicinal chemistry and chemical biology teams use such amino acid derivatives to generate standardized intermediates for SAR (structure-activity relationship) campaigns, including analog series that probe how terminal capping and ester/amide switching influence chemical handling and subsequent functionalization. The methionine thioether side chain remains available for later transformations or stability studies, making Ac-L-Met-OMe a practical starting unit for building methionine-containing motifs with controlled end-group identity.
3. Stable Intermediate for Chemical Studies
Ac-L-Met-OMe is frequently used as a defined chemical intermediate for reactivity and stability investigations that require a consistent methionine-containing reference material. Analytical chemistry and process development groups may employ this derivative to prepare calibration or comparison compounds when evaluating stepwise transformations of methionine residues in protected contexts, such as during intermediate purification development or method qualification for derivative-based workflows. The acetylated amino terminus and methyl ester provide a reproducible starting point for downstream conversions, helping researchers isolate the effects of specific reaction steps rather than variability introduced by uncontrolled terminal functionality.
4. Reference Standards for Methionine Chemistry
Ac-L-Met-OMe is also used in analytical method development and reference standard preparation related to methionine-containing compounds and derivative handling. Laboratories developing LC-MS or related workflows for peptide fragments often require well-characterized methionine derivatives that reflect specific terminal protection states, and Ac-L-Met-OMe provides that defined structure for system suitability checks and fragmentation pattern comparisons. Researchers in proteomics-adjacent method development and chemical analysis of peptide intermediates use this compound to benchmark retention behavior and to support identification of methionine-bearing fragments generated during synthetic or degradation studies.
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