Ac-Tyr(tBu)-OH is an N-acetylated tyrosine derivative bearing a tert-butyl-protected phenolic side chain, placing it in the class of protected amino acid derivatives used for peptide chemistry. The molecule contains an acetylated amino group and a free carboxyl group, while the tyrosine aromatic ring carries a tert-butyl ether protecting group on the phenol, with stereochemistry consistent with the tyrosine scaffold as supplied by the product identity. Its protected phenolic functionality and controlled amine reactivity make it suitable as a building block or substrate for stepwise synthesis and for preparing tyrosine-containing peptide and conjugate intermediates where phenol chemoselectivity is required.
CAT No: CP26704
CAS No:201292-99-1
Synonyms/Alias:AC-TYR(TBU)-OH;201292-99-1;MolPort-020-003-794;ZINC2560350;AKOS025289465;AK170221;FT-0697958;V4165;L-Tyrosine,N-acetyl-O-(1,1-dimethylethyl)-;K-5886
Ac-Tyr(tBu)-OH is an N-acetylated tyrosine derivative bearing a tert-butyl-protected phenolic side chain, providing a protected, uncharged amino acid building block for controlled peptide and peptidomimetic assembly. The acetylated N-terminus and the tBu-protected phenol reduce undesired side reactions during coupling and downstream manipulations, while preserving the tyrosine backbone for incorporation into defined sequences. This reagent is commonly selected when a tyrosine residue must be introduced with the phenolic group masked to maintain chemoselectivity.
1. Peptide Segment Building
Ac-Tyr(tBu)-OH is used as a tyrosine-containing segment component in peptide synthesis workflows where the N-acetylated terminus is required for sequence fidelity and the phenolic side chain must remain protected. Peptide chemistry groups and custom peptide manufacturers employ this building block to assemble peptides and peptidomimetics with controlled N- and side-chain protection patterns, supporting reliable coupling steps and reducing variability from phenol oxidation or side-chain participation. The tert-butyl phenol protection is particularly useful when subsequent steps require conditions that would otherwise compromise an unprotected tyrosine side chain.
2. Protected Tyrosine Intermediate
Ac-Tyr(tBu)-OH serves as a practical protected tyrosine intermediate for preparing downstream amino acid derivatives and sequence-defined fragments used in medicinal chemistry and structure-activity relationship studies. Synthetic chemists value the combination of N-acetylation and phenol protection because it enables transfer of the tyrosine unit into larger constructs without premature side-chain reactivity. This is especially relevant for assembling analog libraries where consistent protection of the phenolic hydroxyl is needed to avoid batch-to-batch differences and to maintain compatibility with standard peptide coupling and fragment condensation strategies.
3. Peptidomimetic SAR Development
Ac-Tyr(tBu)-OH is commonly incorporated into peptidomimetic development programs where tyrosine residues are required but the phenolic functionality must be handled under protected conditions until the desired stage of synthesis. Medicinal chemistry teams use this reagent to build defined analogs for SAR campaigns, ensuring that the tyrosine side chain does not interfere with earlier synthetic transformations. By delivering a tyrosine unit with masked phenol reactivity and an N-acetylated terminus, it supports the preparation of analogs that can later be processed into target-ready peptide-like scaffolds with controlled functional group exposure.
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