Ac-Tyr-NHMe contains the tyrosine-derived amino acid backbone in a peptide-related intermediate format, featuring an N-acetylated (Ac-) amino terminus and a C-terminal N-methylamide (NHMe) that replaces the free carboxyl group. The aromatic phenol side chain of the tyrosine residue remains unprotected and bears a hydroxyl functionality capable of hydrogen bonding and phenolic reactivity, while the backbone contains the amide linkages that define a constrained, non-zwitterionic derivative relative to the free amino acid. Ac-Tyr-NHMe is used in peptide chemistry and chemical biology workflows as a defined tyrosine-containing substrate or building block for preparing longer amide-linked peptides and for studying acyl/amide-forming or tyrosine-side-chain-dependent behavior under controlled synthetic conditions.
CAT No: CP27310
CAS No:6367-14-2
Synonyms/Alias:Ac-Lys(Z)-OH;6367-08-4;MCS-652;AC1LA2DW;SCHEMBL7296591;MolPort-002-893-885;BTB13566;ZINC1628895;AKOS025289400;MCULE-5525775928;AK170127;AM002804;(2S)-2-acetamido-6-(benzyloxycarbonylamino)hexanoicacid;(2S)-2-acetamido-6-(phenylmethoxycarbonylamino)hexanoicacid;(2S)-2-(Acetylamino)-6-[(phenylmethoxy)carbonylamino]hexanoicacid;(2S)-6-{[(BENZYLOXY)CARBONYL]AMINO}-2-ACETAMIDOHEXANOICACID
Ac-Tyr-NHMe is an N-acetylated tyrosine amide (Tyr amide) that provides a protected, peptide-like aromatic amino acid motif with a free phenolic side chain. This structure is commonly used as a short, well-defined building block for studying tyrosine-containing peptide recognition and for preparing model substrates or standards where the C-terminus is converted to a methylamide. By combining an acetylated N-terminus with an amide-form C-terminus, Ac-Tyr-NHMe helps minimize ambiguity from terminal reactivity and supports reproducible downstream coupling, derivatization, and analytical characterization.
1. Peptide Substrate Modeling
Ac-Tyr-NHMe is frequently employed to generate tyrosine-containing peptide mimics for enzymology and substrate specificity studies, where researchers need a defined "mini-peptide" bearing a phenolic tyrosine side chain. The N-acetyl and C-methylamide termini produce a neutral, non-ionizable peptide end pattern that reduces variability associated with free N- or C-termini. This makes the compound useful in assay development workflows for protease, peptidase, or enzyme systems that recognize short peptide motifs, as well as in comparative studies where the tyrosine side chain is the primary variable.
2. Analytical Reference Derivatization
Ac-Tyr-NHMe is also used as a chemically stable reference material for analytical method development and calibration related to tyrosine-containing peptides and peptide-like amides. Because it is a single, well-characterized compound with terminally capped functionality, it can serve as a practical standard for LC-MS workflows, derivatization optimization, and method qualification steps where consistent ionization behavior and chromatographic retention are required. Laboratories that develop workflows for peptide hydrolysates, capped peptide fragments, or tyrosine-containing building blocks often incorporate Ac-Tyr-NHMe to verify derivatization efficiency and instrument response under controlled conditions.
3. Peptidomimetic Intermediate Building Block
Ac-Tyr-NHMe functions as a peptide-derived intermediate for preparing larger peptidomimetic structures and tyrosine-bearing fragments in medicinal chemistry and chemical biology programs. The methylamide C-terminus and acetylated N-terminus provide a convenient platform for further functionalization at the phenolic oxygen when side-chain chemistry is the focus, while keeping the backbone ends protected from undesired coupling or side reactions. This makes the compound valuable for assembling short aromatic amino acid motifs used in SAR (structure-activity relationship) studies, receptor-binding model compounds, and synthetic routes that require a tyrosine unit with capped termini rather than a free amino acid.
4. Chemical Biology Probe Fragment
Ac-Tyr-NHMe is used as a tyrosine-containing fragment in chemical biology workflows where a capped tyrosine motif is needed for constructing probe scaffolds or tagging reagents. The phenolic side chain provides a handle for site-directed derivatization strategies that incorporate aromatic tyrosine chemistry into larger probe molecules, while the acetyl/methylamide termini help maintain a consistent peptide-like microenvironment. Researchers developing labeled peptide mimics, affinity probes, or assay-compatible molecular tools often choose Ac-Tyr-NHMe to ensure the tyrosine functionality is presented in a controlled, terminally capped form.
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