Boc-D-Thz-OH is a protected amino acid derivative featuring a D-configured thiazole-containing side chain (Thz) linked to an amino acid backbone and bearing a tert-butoxycarbonyl (Boc) carbamate on the α-amino group. The molecule contains a free carboxylic acid functionality for coupling chemistry and a Boc-protected nitrogen that suppresses undesired amine reactivity during stepwise synthesis, while the aromatic thiazole ring provides a heteroaromatic handle for electronic and binding studies. It is used as a building block in peptide synthesis and related amide-forming reactions, including workflows where protected amino acids are assembled under controlled chemoselectivity to incorporate thiazole-bearing residues into peptide or peptidomimetic structures.
CAT No: CP25955
CAS No:63091-82-7
Synonyms/Alias:Boc-Thr-OSu;63076-44-8;SCHEMBL721602;MolPort-006-149-899;ZINC1640313;6450AH;KM0699;AKOS025289398;CB-1703;AK170125;N-[(1S,2R)-1-[[(2,5-Dioxo-1-pyrrolidinyl)oxy]carbonyl]-2-hydroxypropyl]carbamicacid1,1-dimethylethylester
Chemical Name:(S)-N-(t-Butyloxycarbonyl)-thiazolidine-4-carboxylic acid
Boc-D-Thz-OH is a Boc-protected D-configured thiazole-containing amino acid building block used as a stereodefined residue for peptide and peptidomimetic synthesis. The thiazole side-chain provides a heteroaromatic motif that can influence conformation, electronics, and downstream reactivity in assembled sequences. As a protected amino acid, it is primarily supplied for controlled incorporation during protected-amino-acid workflows rather than direct biological use.
1. Fmoc-Compatible Peptide Synthesis
Boc-D-Thz-OH is commonly used by peptide chemistry groups to install a D-thiazole-bearing residue in custom peptide sequences where a protected amino acid building block is required for reliable coupling and purification. Peptide manufacturers and academic peptide cores often select this Boc-protected format to streamline segment assembly and to maintain the stereochemical integrity of the D-center during synthesis. The thiazole side chain is particularly valued when researchers want a heteroaromatic handle embedded within the peptide backbone for SAR studies, structural probing, or as a motif in peptidomimetic designs.
2. Peptidomimetic And SAR Building
Boc-D-Thz-OH supports medicinal chemistry programs that develop peptidomimetics and constrained analogs incorporating heteroaromatic pharmacophores. The D-thiazole residue enables the construction of stereochemically defined analog series used in structure-activity relationship workflows, where small changes in residue identity and stereochemistry are used to evaluate effects on physicochemical properties and target-binding hypotheses. In this context, the Boc-protected amino acid form is selected to provide consistent downstream coupling behavior during the rapid synthesis of analog panels for library-style evaluation.
3. Pharmaceutical Intermediate Development
Boc-D-Thz-OH is also used in pharmaceutical intermediate development when a protected, stereodefined thiazole-containing amino acid unit is required as a building block for further derivatization. Process and custom synthesis teams rely on such protected intermediates to control functional group compatibility across multi-step sequences, enabling the preparation of advanced intermediates that later feed into larger molecule assembly. The presence of the Boc-protected amino functionality and the heteroaromatic thiazole side chain makes it a practical choice for constructing defined fragments used in medicinal chemistry and specialty chemical manufacturing.
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