Boc-D-MeTyr(Bzl)-OH is a protected, non-natural amino acid derivative featuring a D-configured tyrosine backbone bearing a methyl substituent on the side chain and a benzyl-protected phenolic oxygen, with the amino group protected as a Boc (tert-butoxycarbonyl) carbamate. The molecule contains a Boc-protected α-amino functionality and a free carboxylic acid, while the tyrosine-derived aromatic ring bears a benzyl ether that modulates phenol reactivity during peptide assembly. As a stepwise peptide synthesis intermediate, it provides orthogonal protection for the phenolic side chain and the α-amino group, supporting controlled formation of peptide bonds and subsequent deprotection-based access to the side-chain hydroxyl functionality for structure-activity studies or chemical biology probe construction.
CAT No: CP25339
CAS No:138774-98-8
Synonyms/Alias:138774-98-8;Boc-D-MeTyr(Bzl)-OH;AmbotzBAA5560;BOC-D-METYR-OHCHA;Boc-D-N-Me-Tyr(Bzl)-OH;Boc-N-Me-D-Tyr(Bzl)-OH;TMA034;D-Tyrosine,N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-O-(phenylmethyl)-;CTK4C1391;Boc-N-methyl-O-benzyl-D-tyrosine;MolPort-003-894-380;ZINC2392273;AKOS015836750;AC-19305;AK170184;RT-011738;K-4488;D-Tyrosine,N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-O-(phenylmethyl)-;(2R)-3-[4-(benzyloxy)phenyl]-2-[(tert-butoxycarbonyl)(methyl)amino]propanoicacid
Chemical Name:N-alpha-(t-Butyloxycarbonyl)-N-alpha-methyl-O-benzyl-D-tyrosine
Boc-D-MeTyr(Bzl)-OH is a protected D-amino acid building block featuring a Boc-protected amino group and a benzyl-protected side-chain phenolic oxygen, paired with a benzyl substituent on the tyrosine ring (MeTyr(Bzl) motif). This protected, stereodefined derivative is designed for peptide and peptidomimetic synthesis workflows where controlled incorporation of a D-configuration residue and orthogonal side-chain protection are required. The combination of Boc and benzyl-type protections supports robust handling during coupling and subsequent downstream deprotection strategies to access target peptide or intermediate structures.
1. D-Amino Acid Peptide Building
Boc-D-MeTyr(Bzl)-OH is used as a stereodefined residue for constructing D-containing peptides and peptidomimetics in custom peptide synthesis. Researchers selecting this building block typically aim to introduce conformational and proteolytic stability effects associated with D-amino acid incorporation, while maintaining a protected phenolic side chain to prevent undesired side reactions during chain assembly. The Boc protection on the amino terminus supports standard peptide coupling workflows, and the benzyl-protected tyrosine side-chain functionality helps preserve chemoselectivity until the designed deprotection stage in the synthesis sequence.
2. Side-Chain Protected Tyrosine Analogues
Boc-D-MeTyr(Bzl)-OH supports the preparation of tyrosine-analog peptide segments where phenolic oxygen protection is necessary for clean assembly and later functionalization. Peptide medicinal chemistry groups commonly use this type of protected derivative to control when the phenolic functionality is revealed, enabling downstream steps such as selective derivatization or incorporation into larger bioactive or screening libraries without premature oxidation or coupling. The benzyl-protected side chain also helps maintain compatibility with conditions used for peptide bond formation, minimizing side-chain interference and improving reproducibility across library synthesis campaigns.
3. Peptidomimetic Intermediate Development
Boc-D-MeTyr(Bzl)-OH is also applied as a protected amino acid intermediate for manufacturing and development of peptidomimetic scaffolds that require a D-configuration aromatic residue with masked functionality. Pharmaceutical intermediate development teams use such building blocks to assemble advanced intermediates that later undergo deprotection and further elaboration into final coupling partners, constrained analogs, or specialty fragments for SAR studies. The protected amino group and benzyl-type side-chain protection provide practical stability during multi-step synthetic sequences, supporting reliable scale-up of intermediate preparation for medicinal chemistry programs.
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