Ac-Ala-OMe

Ac-Ala-OMe contains an alanine residue bearing an N-acetyl (Ac-) group and a C-terminal methyl ester (OMe), classifying it as an amino acid ester derivative rather than a free amino acid. The molecule presents an α-amino functionality acylated by acetylation and a carboxyl group converted to a methyl ester, with a side chain consisting of a methyl group characteristic of alanine; stereochemistry is not specified in the name. Ac-Ala-OMe is used in peptide chemistry and related synthetic studies as a protected/activated alanine building block for constructing amide linkages in stepwise synthesis or for preparing alanine-containing intermediates and analytical standards.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP27059

CAS No:3619/2/1

Synonyms/Alias:(S)-Methyl2-acetamidopropanoate;3619-02-1;AC-ALA-OME;N-Acetyl-L-alaninemethylester;methyl(2S)-2-acetamidopropanoate;Alanine,N-acetyl-,methylester;Ac-L-Ala-OMe;AmbotzAAA1912;AC1OCUYD;N-Acetyl-L-alaninemethyl;N-acetylalaninemethylester;Acetyl-L-alaninemethylester;SCHEMBL805648;CHEMBL3278816;CTK3E7879;FQGVVDYNRHNTCK-BYPYZUCNSA-N;MolPort-003-922-442;ZINC402099;4572AB;ANW-58540;ZINC00402099;AKOS006238313;AJ-21826;AK-80482;AM008881

Chemical Name:N-alpha-Acetyl-L-alanine methyl ester

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M.F/Formula
C6H11NO3
M.W/Mr.
145.16

Ac-Ala-OMe is an N-acetylated alanine methyl ester that presents a protected amino acid backbone for downstream peptide and peptidomimetic assembly. By masking the amino group as an acetamide and converting the carboxyl group to a methyl ester, it behaves as a stable, non-zwitterionic building block for controlled fragment coupling and for preparing alanine-containing intermediates used in structure-activity and method development workflows.

1. Peptide Fragment Building

Ac-Ala-OMe is used as a protected alanine building block to generate short peptide fragments and alanine-containing intermediates in custom peptide synthesis workflows. Researchers and peptide manufacturing groups value the N-acetyl and methyl ester protection pattern because it supports stepwise construction while reducing unwanted side reactions from a free amino or carboxyl group during fragment handling and purification.

2. Solution-Phase Coupling Intermediate

Ac-Ala-OMe is commonly employed in solution-phase peptide chemistry as a defined, isolable precursor for segment condensation strategies where an alanine unit with a masked termini is required. Medicinal chemistry and peptidomimetic development teams use it to prepare standardized intermediates that can be further transformed into longer sequences or analogs, enabling consistent material preparation for SAR studies and analytical characterization.

3. Peptidomimetic and SAR Studies

Ac-Ala-OMe supports the preparation of alanine-derived peptidomimetic scaffolds and SAR-relevant analog series where controlled backbone functionality is needed. Chemical biology groups and medicinal chemistry teams often rely on such protected amino acid derivatives to build libraries of closely related structures, keeping the reactive termini protected until the final stages of synthesis and allowing parallel synthesis and comparative analytical evaluation.

4. Analytical Reference Material

Ac-Ala-OMe is used as a reference or calibration component in analytical method development for workflows that monitor peptide-like fragments, amide/ester-containing intermediates, or alanine-based building blocks. Analytical chemistry teams use it to validate LC/UV or LC-MS retention behavior and to confirm derivatized fragment identity during process development, impurity profiling, and intermediate qualification for peptide synthesis programs.

Size
5 g;25 g;
InChI
1S/C6H11NO3/c1-4(6(9)10-3)7-5(2)8/h4H,1-3H3,(H,7,8)/t4-/m0/s1
InChI Key
FQGVVDYNRHNTCK-BYPYZUCNSA-N
Canonical SMILES
CC(C(=O)OC)NC(=O)C

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