Fmoc-Tyr(malonyl-di-OtBu)-OH is an Fmoc-protected tyrosine derivative bearing a malonyl group masked as a di-tert-butyl ester on the phenolic side chain, making it a protected amino acid suitable for peptide chemistry. The molecule contains an N-terminal Fmoc carbamate, a free carboxylic acid at the C-terminus, and a tyrosine-derived aromatic ring whose phenolic oxygen is substituted with the malonyl-di-OtBu functionality, while the side-chain carbonyl-bearing substituent is sterically and electronically protected by tert-butyl ester groups. In synthesis, it functions as a stepwise building block for solid-phase or solution-phase assembly where controlled handling of the tyrosine phenol and the malonyl ester motif is required for downstream elaboration or for preparing peptide conjugates and labeled analogues that retain the malonyl group until deprotection.
CAT No: CP26479
CAS No:168135-77-1
Synonyms/Alias:168135-77-1;Fmoc-Tyr(Malonyl-Di-Otbu)-OH;C35H39NO9;6999AH;ZINC71788133;AKOS015910198;Na-Fmoc-O-di-tert-butyl-malonyl-L-tyrosine;A-9334;N-Fmoc-O-[Bis(tert-butoxycarbonyl)methyl]tyrosine;I14-40701
Fmoc-Tyr(malonyl-di-OtBu)-OH is an Fmoc-protected tyrosine derivative bearing a malonyl group on the phenolic side chain, where both malonate carboxylates are masked as tert-butyl esters. The molecule combines a stereochemically defined amino acid core with an aromatic phenol-derived substitution pattern and a highly functional, acid-labile malonate diester motif. The Fmoc group enables base-mediated N-deprotection under peptide-synthesis conditions, while the tert-butyl ester protecting groups support orthogonal side-chain handling during stepwise assembly. The presence of the malonyl diester provides a controlled platform for subsequent decarboxylation, hydrolysis, or conversion into carboxylate-bearing intermediates relevant to peptide analogs and downstream synthetic transformations.
1. Peptide Synthesis
Fmoc-Tyr(malonyl-di-OtBu)-OH supports solid-phase peptide coupling workflows where the Fmoc carbamate protects the amino function for iterative chain elongation. The tyrosine backbone provides a chiral amino acid template, and the malonyl-di-OtBu side-chain substituent functions as a protected, multi-carboxylate handle that can be retained during coupling and selectively transformed after peptide assembly. Side-chain protection by tert-butyl esters allows orthogonal manipulation relative to the Fmoc group, enabling controlled deprotection sequences for generating carboxylate-rich peptide derivatives. The resulting peptide building block can be used to construct tyrosine-containing sequences that incorporate malonate-derived functionality for further derivatization and structure-activity relationship studies.
2. Amino Acid Derivatization
Fmoc-Tyr(malonyl-di-OtBu)-OH can be applied in amino acid derivatization strategies that require installation of a protected dicarboxylate motif on a tyrosine side chain. The malonyl diester architecture provides two esterified carboxyl groups that can be hydrolyzed or converted into activated carboxylates after removing tert-butyl protection, enabling formation of amide, ester, or mixed anhydride derivatives. The Fmoc-protected amine allows isolation and purification as a stable chiral intermediate, while maintaining compatibility with common peptide-coupling reagents for downstream functionalization. The compound therefore serves as a chemically defined precursor for generating tyrosine-based carboxylate-rich building blocks and for preparing reference materials used in synthetic method development.
3. Peptidomimetics And SAR
Fmoc-Tyr(malonyl-di-OtBu)-OH is suitable for peptidomimetic construction where tyrosine side-chain modification is used to tune charge density, hydrogen-bonding capacity, and conformational preferences. The malonyl diester substituent can be processed into carboxylate-bearing analogs that mimic acidic motifs, supporting SAR studies that probe how multi-carboxylate patterns affect molecular recognition. The orthogonality between Fmoc deprotection and tert-butyl ester removal enables stepwise generation of functionalized analogs while preserving the integrity of other protecting groups on complex scaffolds. The resulting modified tyrosine residues can be incorporated into peptide analogs and fragment libraries to support structure-function investigations across diverse synthetic chemistry programs.
4. Bioconjugation Chemistry
Fmoc-Tyr(malonyl-di-OtBu)-OH can be employed in bioconjugation chemistry workflows that require controlled introduction of carboxylate functionalities for coupling to amine- or hydrazide-bearing biomolecules. The malonate diester provides a protected route to carboxylate groups that can be unveiled under conditions compatible with peptide-derived intermediates, enabling subsequent activation for conjugation chemistry. The aromatic tyrosine scaffold supports conjugate design where phenolic substitution patterns influence local polarity and spacing to the reactive handles. The compound's protected amino acid form also facilitates preparation of well-defined conjugation-ready intermediates, supporting reproducible downstream derivatization in biochemical research and analytical reference development.
5. Pharmaceutical Intermediate Preparation
Fmoc-Tyr(malonyl-di-OtBu)-OH is applicable as a chiral, protected amino acid intermediate for manufacturing-oriented synthesis of functionalized peptide-like building blocks used in fine chemical production. The Fmoc group provides a stable N-protection strategy that can be removed on demand, while the tert-butyl ester-protected malonate enables controlled generation of diacid or activated carboxylate intermediates during process sequencing. The defined aromatic side-chain substitution supports reproducible incorporation into complex intermediates where side-chain functionality must survive coupling steps and then be converted to reactive acid forms. The compound can therefore be integrated into process chemistry routes that require orthogonal protection logic for scalable preparation of carboxylate-rich amino acid derivatives and peptide coupling feedstocks.
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