Ac-Glu-OMe contains a glutamic acid-derived α-amino acid framework in which the α-carboxyl group is converted to a methyl ester (-CO2Me) and the α-amino group is acetylated (Ac-), forming an amino acid ester with an N-acetyl protecting group. The side chain retains the γ-carboxyl functionality characteristic of glutamate, providing a polar acidic group that can be used for controlled chemoselective transformations or further derivatization while the acetylated amino terminus and methyl ester modulate reactivity. Ac-Glu-OMe is used as a chemically defined glutamate building block and intermediate for preparing peptide-related derivatives, for studying side-chain-dependent properties in synthetic sequences, and for constructing more complex amino acid conjugates where esterification and N-acetylation help manage functional-group compatibility.
CAT No: CP26495
CAS No:17015-15-5
Synonyms/Alias:(S)-4-Acetamido-5-methoxy-5-oxopentanoicacid;17015-15-5;Ac-glu-ome;AC1ODVAY;SCHEMBL4577282;CTK8C4905;MolPort-027-834-920;ZINC2572074;8722AA;ANW-73469;Acetyl-L-glutamicacidalpha-methylester;AJ-41959;AK-61131;TC-162214;K-5253;(4S)-4-acetamido-5-methoxy-5-oxopentanoicacid
Ac-Glu-OMe is an N-acetylated glutamate methyl ester that functions as a protected, activated glutamate building block for peptide-related synthesis and downstream derivatization. By masking the amino group as an acetamide and esterifying the side-chain carboxyl as a methyl ester, this compound provides a controlled reactivity profile that is commonly leveraged in fragment coupling, synthesis of glutamate-containing motifs, and preparation of standards or intermediates where selective functional group handling is required.
1. Glutamate-Containing Peptide Building
Ac-Glu-OMe is used as a glutamate-derived fragment in peptide synthesis workflows where the N-terminus is pre-acetylated and the side-chain carboxyl is ester-protected as a methyl ester. Researchers in custom peptide manufacturing and peptide chemistry laboratories employ this type of protected glutamate derivative to assemble short peptides and peptidomimetic segments with controlled chemoselectivity during coupling and subsequent functional group transformations. The methyl ester and acetamide pattern help manage side reactions associated with free carboxyl and free amino functionality, supporting reliable downstream processing when glutamate residues must be introduced as defined intermediates.
2. Pharmaceutical Intermediate Development
Ac-Glu-OMe is also positioned as a practical intermediate for medicinal chemistry and process development programs that require glutamate-derived scaffolds. Synthetic teams use this compound to generate defined glutamate functional motifs en route to more complex structures such as protected amino acid derivatives, side-chain-modified analogs, and other intermediates that retain the glutamate backbone while allowing later conversion of ester functionality. Its protected amino and ester groups make it a convenient starting point for stepwise elaboration in small-molecule and peptidomimetic synthesis, including workflows where protecting-group strategy must be compatible with subsequent coupling or functional group interconversions.
3. Ester-Stage Derivatization
Ac-Glu-OMe is frequently used in derivatization sequences that treat the methyl ester as a handle for controlled conversion to other carboxylate forms or for transient protection during multi-step synthesis. Chemical biology and materials chemistry groups may incorporate glutamate-derived ester intermediates to produce defined carboxylate-bearing products with predictable stoichiometry and purification behavior. Because the molecule is already N-acetylated, it also offers a reduced risk of unwanted amide/amine side chemistry compared with unprotected glutamate derivatives, supporting cleaner downstream transformations when the goal is to access glutamate-containing products with specific functional group states.
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