Boc-D-Tyr(Et)-OH is a protected, non-natural amino acid derivative based on the D-configuration of tyrosine, bearing a tert-butoxycarbonyl (Boc) group on the amino functionality and an O-ethyl substituent on the phenolic side chain. The molecule contains both an N-Boc-protected amino group and a carboxylic acid, while the tyrosine aromatic ring carries a phenoxyethyl ether that modulates side-chain polarity and reduces phenolic nucleophilicity relative to the free phenol. As a stepwise peptide-synthesis building block, the Boc protection supports controlled amide bond formation at the α-amino group, and the O-ethyl phenol protection pattern is used to manage chemoselectivity during assembly of peptide derivatives and in the preparation of tyrosine-containing analogues for structure-activity or labeling studies.
CAT No: CP26040
CAS No:76757-92-1
Synonyms/Alias:Boc-D-Tyr(Et)-OH;76757-92-1;Boc-O-ethyl-D-tyrosine;AmbotzBAA1456;SCHEMBL3188805;15095_FLUKA;MolPort-003-926-643;NCLAAKQIHUIOIV-CYBMUJFWSA-N;ZINC2539213;9462AE;CB-077;KM1794;AKOS015836443;AK170143;AN-36914;N-(tert-butoxycarbonyl)-O-ethyl-D-tyrosine;FT-0641606;D-Tyrosine,N-[(1,1-dimethylethoxy)carbonyl]-O-ethyl-;(2R)-2-(tert-butoxycarbonylamino)-3-(4-ethoxyphenyl)propanoicacid;(2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-ethoxyphenyl)propanoicacid
Chemical Name:N-alpha-t-Butyloxycarbonyl-O-ethyl-D-tyrosine
Boc-D-Tyr(Et)-OH is a protected, D-configured tyrosine derivative designed for peptide and peptidomimetic synthesis. The backbone amino group is protected as a Boc carbamate, while the phenolic side chain is O-ethylated (Tyr(Et)), providing controlled reactivity during coupling and minimizing side-chain interference. This reagent is commonly used by peptide chemists and medicinal chemistry teams to assemble D-amino acid-containing sequences with defined stereochemistry and side-chain protection.
1. D-Amino Acid Peptide Synthesis
Boc-D-Tyr(Et)-OH is used as a building block for solid-phase or solution-phase peptide synthesis where incorporation of a D-tyrosine residue is required for stereochemical control and sequence design. Peptide synthesis groups in academic and industrial medicinal chemistry workflows select this protected derivative to keep the phenolic oxygen masked as an ethyl ether during chain assembly, reducing undesired side reactions and supporting consistent coupling outcomes. The Boc-protected amino group aligns with standard protected-amino-acid handling strategies for assembling D-residue-containing peptides and peptide analogs used in structure-activity relationship studies and chemical biology tool development.
2. Side-Chain Protected Tyrosine Building Block
Boc-D-Tyr(Et)-OH is frequently chosen when tyrosine side-chain chemistry must be deferred until later stages of synthesis, such as when the final target requires selective phenol functionalization or controlled derivatization. Peptide and peptidomimetic developers use the O-ethyl protection to maintain the aromatic phenol in a non-reactive state throughout intermediate steps, enabling downstream transformations after the peptide scaffold is assembled. This makes the reagent practical for preparing tyrosine-containing segments for subsequent modification strategies, including conversion to more reactive phenol derivatives during final processing or for generating analog libraries.
3. Medicinal Chemistry Peptidomimetic Intermediates
Boc-D-Tyr(Et)-OH supports medicinal chemistry programs that build D-amino-acid-containing peptidomimetics and constrained peptide analogs as synthetic intermediates en route to larger constructs. Research groups developing bioactive peptide-like molecules often rely on protected D-tyrosine derivatives to maintain stereochemical integrity and to manage functional-group compatibility across multi-step synthesis and fragment coupling. The Boc/ethyl-phenol protection pattern helps keep the reagent orthogonal to many common peptide-manufacturing conditions, supporting efficient assembly of complex intermediates used for SAR generation and chemical biology assay development.
4. Custom Peptide Manufacturing Research
Boc-D-Tyr(Et)-OH is used in custom peptide manufacturing research and internal development workflows where defined amino acid protection patterns are required for reproducible synthesis of D-tyrosine-containing sequences. Contract research and process development teams value such protected building blocks for planning stepwise assembly and for reducing variability associated with side-chain reactivity during scale-up of peptide intermediates. By providing a stable, protected tyrosine unit with masked phenolic functionality, the reagent fits into controlled peptide synthesis pipelines that culminate in later-stage phenol deprotection or selective modification to match the intended final peptide format.
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