Boc-D-Thr-OH is a protected amino acid derivative of D-threonine bearing an Nα-Boc (tert-butoxycarbonyl) protecting group and a free carboxylic acid, placing it in the class of Boc-protected amino acids used as building blocks for peptide assembly. The molecule contains both an amino functionality masked by the Boc carbamate and a carboxyl group, while the threonine side chain features a β-hydroxyl group that can participate in hydrogen bonding and can be used for further derivatization during peptide or conjugate synthesis. In synthetic workflows, this protected analogue serves as a precursor for stepwise coupling in peptide synthesis and for preparing threonine-containing peptide derivatives where chemoselective control of the amine is required.
CAT No: CP25896
CAS No:55674-67-4
Synonyms/Alias:Boc-D-Nle-OH;Boc-D-norleucine;55674-63-0;(R)-2-((tert-Butoxycarbonyl)amino)hexanoicacid;AmbotzBAA1284;15176_ALDRICH;SCHEMBL3448997;15176_FLUKA;CTK8B3231;tert.-butoxycarbonyl-D-norleucine;MolPort-003-725-662;ZIOCIQJXEKFHJO-MRVPVSSYSA-N;ZINC1576258;ANW-42036;AKOS015907952;AM82587;AJ-27318;AK-81112;KB-48284;TR-019621;FT-0629990;V6600;K-9928;I14-25568
Chemical Name:N-alpha-t-Butyloxycarbonyl-D-threonine
Boc-D-Thr-OH is a D-configured threonine building block protected at the amino group with a Boc (tert-butoxycarbonyl) group, provided as the free carboxylic acid for downstream coupling chemistry. Its side chain contains a hydroxyl-bearing threonine functionality, making it a common stereodefined precursor for assembling modified peptides and peptide segments where D-amino acid incorporation is desired. The Boc protection supports standard peptide intermediate workflows, while the D stereochemistry enables control over conformational and protease-recognition properties in synthetic peptide design.
1. D-Amino Acid Peptide Segments
Boc-D-Thr-OH is used by peptide synthesis groups to introduce D-threonine residues into peptide segments for structure-function studies and backbone stereochemical control. The Boc-protected amino group allows chemists to couple the building block under peptide assembly conditions to generate D-configured sequences, which are frequently employed in peptide library construction and SAR-focused analog generation. The threonine side-chain hydroxyl also supports further derivatization when hydroxyl protection or side-chain functionalization is required for the target peptide architecture.
2. Solid-Phase Peptide Synthesis Building Block
Boc-D-Thr-OH is frequently selected as a protected amino acid intermediate for solid-phase peptide synthesis workflows that require stereodefined D-amino acid incorporation. In custom peptide manufacturing and academic peptide chemistry, it supports the preparation of D-containing peptides where residue-level stereochemistry is used to tune folding behavior, stability against enzymatic degradation, or conformational preferences. The protected amino functionality and free carboxylic acid provide the key handles needed for sequential chain assembly, while the threonine hydroxyl offers a chemically informative side chain for downstream modification strategies.
3. Peptidomimetic And SAR Analog Development
Boc-D-Thr-OH supports medicinal chemistry and chemical biology teams developing peptidomimetics and stereochemically constrained analogs by enabling the systematic placement of D-threonine within peptide-like scaffolds. Researchers use D-amino acid substitutions to probe how stereochemistry at a specific position influences structure, presentation of side-chain hydroxyl groups, and overall physicochemical behavior of the analog series. The Boc-protected format streamlines incorporation into peptide-derived intermediates used for iterative SAR campaigns, where residue identity and stereochemistry must be controlled with high fidelity.
4. Pharmaceutical Intermediate For Modified Peptides
Boc-D-Thr-OH is also used as a pharmaceutical intermediate building block for preparing D-containing peptide fragments that serve as upstream inputs to larger synthetic programs. Process and development chemists rely on stereodefined amino acid intermediates to reduce variability when assembling complex peptide structures, including sequences intended for further functionalization or conjugation downstream. The combination of D stereochemistry, Boc-protected amine, and threonine hydroxyl functionality makes this building block particularly useful when the downstream target requires a specific stereochemical outcome at the amino acid residue level.
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