Boc-D-Tyr(Me)-OH is a protected, non-natural stereochemical variant of tyrosine in which the amino acid framework is Nα-Boc-protected and the phenolic side chain bears a methyl substituent. The molecule contains a free carboxylic acid and a Boc-protected α-amino group, with the aromatic phenol converted to a Me-substituted phenolic ether/phenol derivative characteristic of Tyr(Me) substitution while retaining the D stereochemical designation indicated by the name. This protected amino acid derivative is used as a stepwise building block for peptide synthesis and related amino acid coupling chemistry, where the Boc group helps control chemoselectivity during assembly and the modified tyrosine side chain provides a handle for studying or incorporating altered aromatic functionality in peptide and conjugate structures.
CAT No: CP27362
CAS No:68856-96-2
Synonyms/Alias:BOC-D-TYR(ME)-OH;68856-96-2;D-Tyrosine,N-[(1,1-dimethylethoxy)carbonyl]-O-methyl-;(2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-methoxyphenyl)propanoicacid;Boc-L-phe(4-OCH3)-OH;Boc-4-methoxy-D-Phe-OH;Boc-4-Methoxy-D-Phenylalanine;SCHEMBL1308867;CTK5C8550;SLWWWZWJISHVOU-GFCCVEGCSA-N;ZINC2539215;AKOS015836435;AKOS015907893;CB-1296;AC-16868;AJ-38817;AK170133;KB-48234;FT-0641213;N-(tert-butoxycarbonyl)-O-methyl-D-tyrosine;Y-9417;I14-26497;(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionicacid;(R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionicacid;(R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propanoicacid
Boc-D-Tyr(Me)-OH is a protected D-configured tyrosine derivative bearing a Boc-protecting group on the amino functionality and a methyl-substituted phenolic side chain (Me) on the aromatic hydroxyl. This structure provides a stable, side-chain-protected tyrosine building block that is commonly handled as an amino acid intermediate for peptide assembly, especially where controlled reactivity of the phenolic group is required during coupling and subsequent downstream steps. The Boc protection supports established peptide synthesis workflows, while the D stereochemistry enables access to D-amino acid-containing sequences for peptide design and structure-property studies.
1. D-Amino Acid Peptide Synthesis
Boc-D-Tyr(Me)-OH is used by peptide chemists to incorporate D-tyrosine motifs into protected peptide segments, enabling the preparation of D-amino acid-containing peptides used for conformational control and proteolysis-resistance studies in chemical biology. The Boc group allows straightforward handling in peptide coupling workflows, while the methyl-protected aromatic hydroxyl helps prevent unwanted side reactions during chain assembly. Researchers commonly employ this building block when they need a tyrosine side chain that remains masked during synthesis, reducing variability caused by phenolic reactivity and supporting reproducible generation of peptide libraries and custom sequences.
2. Protected Tyrosine Side-Chain Intermediates
Boc-D-Tyr(Me)-OH serves as a practical intermediate for downstream tyrosine-functional peptide construction where the aromatic hydroxyl must be kept protected until the desired stage of synthesis or modification. In medicinal chemistry and peptide drug discovery research, this type of protected tyrosine derivative is frequently selected to manage chemoselectivity during multi-step assembly, particularly when additional reactive groups are present elsewhere in the peptide or when sequential functionalization is planned. By using a side-chain-protected tyrosine building block with D stereochemistry, developers can better control when and where phenolic derivatization occurs, improving the reliability of intermediate handling and final product consistency.
3. Peptide Library And SAR Studies
Boc-D-Tyr(Me)-OH is widely applied in peptide library synthesis for structure-activity relationship (SAR) investigations that compare stereochemical variants and tyrosine side-chain presentation within otherwise matched peptide backbones. Chemical biology groups and medicinal chemistry teams use D-tyrosine-containing analogs to probe how stereochemistry and side-chain masking influence peptide behavior during screening workflows, including assay development and lead optimization. The protected form supports efficient parallel synthesis of multiple peptide analogs, while the methyl-substituted phenolic protection helps maintain uniform side-chain chemistry across library members until later stages, supporting more interpretable SAR outcomes.
4. Pharmaceutical Intermediate Development
Boc-D-Tyr(Me)-OH is also used in pharmaceutical intermediate development as a protected amino acid building block for manufacturing research and process development of peptide-based candidates or peptide-like intermediates. Development teams rely on stable, protected tyrosine derivatives to reduce side reactions and improve handling robustness during scale-up of protected peptide segments. The Boc-protected amino group and the protected aromatic hydroxyl enable controlled conversion into larger intermediates, supporting downstream assembly strategies where defined functional group timing is important for quality-by-design approaches in chemical development workflows.
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