Ac-Met-NH2 is an N-acetylated methionine amide featuring the methionine side chain with a thioether sulfur and a terminal primary carboxamide (-CONH2) rather than a free carboxylic acid, placing it in the class of amino acid amides and acylated amino acid derivatives. The molecule bears an N-acetyl (Ac-) group on the amino terminus, leaving the methionine α-amino functionality incorporated as an amide, and it presents the characteristic thioether side-chain for chemical derivatization or redox-sensitive labeling chemistry while maintaining the α-amide and α-carbonyl connectivity typical of peptide-related building blocks. Ac-Met-NH2 is used as a defined methionine-containing substrate or intermediate in peptide chemistry and analytical method development, including studies that require a methionine residue with controlled terminal functionality for conjugation, derivatization, or structure-property investigations.
CAT No: CP26832
CAS No:23361-37-7
Synonyms/Alias:Ac-met-nh2;23361-37-7;2-(Acetylamino)-4-(methylsulfanyl)butanamide#;AC1OCX9V;Acetyl-L-methionineamide;SCHEMBL1694618;CTK8F7542;AJQATZBTQNYZFO-LURJTMIESA-N;ZINC2165894;6102AH;AKOS006272969;CJ-33297;KB-47133;(2S)-2-acetamido-4-methylsulfanylbutanamide;FT-0638317;K-6404
Ac-Met-NH2 is an N-acetylated methionine amide featuring a protected, non-ionizable carboxamide terminus that is commonly used as a defined methionine-containing building block in peptide chemistry and chemical biology workflows. The Met side chain provides a thioether functionality that is frequently leveraged in controlled oxidation/reduction studies and in the preparation of methionine analogs for analytical or mechanistic experiments. As a short, capped amino acid derivative, Ac-Met-NH2 is typically selected when a stable, terminally protected methionine unit is required without introducing free carboxyl or free amino reactivity.
1. Peptide Segment Capping
Ac-Met-NH2 is used by peptide synthesis teams and custom peptide manufacturers as a capped methionine building block for preparing short peptides, peptide standards, and sequence-defined fragments where terminal functionality must be controlled. The N-acetyl and C-amide pattern helps maintain a consistent peptide microenvironment during downstream coupling steps and analytical handling, reducing variability that can arise from free termini. Researchers often incorporate this derivative when methionine-containing segments are needed as model substrates for studying terminal effects on reactivity, stability, or processing in chemical and biochemical assays.
2. Methionine Oxidation Studies
Ac-Met-NH2 is routinely used in chemical biology and analytical chemistry to generate defined methionine-containing substrates for oxidation state investigations, including workflows that compare thioether-containing methionine derivatives under controlled oxidative conditions. The thioether side chain provides a chemically specific handle for monitoring conversion to oxidized methionine species using LC-MS or related analytical methods. This makes Ac-Met-NH2 a practical choice for mechanistic experiments and stability testing of methionine-containing peptide fragments where reproducible starting material is essential.
3. Analytical Reference Material
Ac-Met-NH2 serves as a well-defined reference compound for method development and quantification in mass spectrometry-based assays targeting methionine-containing motifs or oxidation products. Analytical laboratories use it to validate chromatographic behavior, retention time alignment, and fragmentation patterns for methionine amide standards, particularly when building calibration sets or internal reference panels. Because the compound is terminally capped, it offers a consistent chemical identity that helps reduce ambiguity when interpreting assay readouts for methionine-derived analytes.
4. Peptidomimetic Intermediate Building Block
Ac-Met-NH2 is also employed in medicinal chemistry and peptidomimetic development as a compact methionine-derived intermediate for assembling constrained or terminally protected structures. Teams working on structure-activity relationship studies often prefer capped amino acid derivatives to control functional group presentation during stepwise synthesis and to simplify purification relative to free amino acid forms. The methionine amide motif supports downstream derivatization strategies aimed at producing sequence-defined mimics used in chemical biology tool development and analytical substrate panels.
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