Boc-O-benzyl-L-Threonine is a protected threonine derivative in which the amino acid backbone is modified with a Boc-protecting group on the α-amino functionality and an O-benzyl ether protecting group on the threonine side-chain hydroxyl. The molecule contains a free carboxylic acid group and bears an L-threonine stereochemical configuration as indicated by the name, while the benzylated side-chain hydroxyl and Boc carbamate reduce chemoselectivity issues during peptide coupling steps. In peptide synthesis workflows, it functions as a protected amino acid building block that supports controlled formation of amide bonds while maintaining side-chain protection for subsequent deprotection and further elaboration of threonine-containing peptide intermediates.
CAT No: CP01911
CAS No:15260-10-3
Synonyms/Alias:Boc-Thr(Bzl)-OH;Boc-O-benzyl-L-threonine;15260-10-3;N-(tert-Butoxycarbonyl)-O-benzyl-L-threonine;Boc-Thr(Bzl);CTXPLTPDOISPTE-YPMHNXCESA-N;N-alpha-tert-BOC-o-benzyl-L-threonine;ST055877;N-((1,1-Dimethylethoxy)carbonyl)-O-(phenylmethyl)-L-threonine;L-Threonine,N-((1,1-dimethylethoxy)carbonyl)-O-(phenylmethyl)-;L-Threonine,N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-;(2S,3R)-2-[(tert-butoxy)carbonylamino]-3-(phenylmethoxy)butanoicacid;N-tert-Butoxacarbonyl-O-benzyl-L-threonine;PubChem12946;AC1Q29DB;N-Boc-O-benzyl-L-threonine;15405_ALDRICH;SCHEMBL400187;466697_ALDRICH;AC1LU898;15405_FLUKA;CTK8B0843;MolPort-003-983-071;ACT05072;ZINC1576312
Boc-O-benzyl-L-Threonine is a protected L-threonine derivative designed for peptide synthesis workflows, featuring a Boc-protected amino group and an O-benzyl-protected side-chain hydroxyl that provides orthogonal stability during assembly. The threonine stereocenter is retained in the L-configuration, enabling incorporation into peptide sequences with controlled functional group chemistry for downstream deprotection and coupling strategies. This reagent is commonly selected when a threonine side-chain needs to remain masked as an O-benzyl ether during protected-amino-acid handling and segment condensation.
1. Solid-Phase Peptide Synthesis
Boc-O-benzyl-L-Threonine is used as a threonine building block in solid-phase peptide synthesis where the Boc group supports stepwise amino protection management and the O-benzyl ether helps prevent side-chain hydroxyl participation under typical coupling and deprotection conditions. Custom peptide synthesis groups and peptide chemistry teams rely on this protected form to maintain side-chain integrity while assembling peptides that contain threonine residues for subsequent functionalization or native-side-chain generation. The O-benzyl protection is particularly valuable when threonine side-chain reactivity must be suppressed to avoid undesired branching, acylation, or side reactions during chain elongation.
2. Solution-Phase Segment Coupling
Boc-O-benzyl-L-Threonine supports solution-phase peptide synthesis and segment condensation strategies where protected amino acid residues must remain stable through activation, coupling, and intermediate purification steps. Peptide process development and medicinal chemistry laboratories use this building block to prepare threonine-containing peptide fragments with controlled side-chain protection, enabling reliable fragment assembly before final global deprotection. The Boc/O-benzyl protection pattern allows chemists to plan downstream deprotection sequences so that the threonine side-chain hydroxyl can be revealed at a chosen stage, improving control over chemoselectivity in complex peptide architectures.
3. Threonine Side-Chain Functional Control
Boc-O-benzyl-L-Threonine is frequently selected when the threonine hydroxyl must be masked to control later derivatization of the peptide side chain, such as introducing orthogonal handles or generating a defined alcohol functionality after assembly. Chemical biology and peptide engineering teams use this reagent to build peptides where threonine side-chain reactivity needs to be deferred until after sequence construction, purification, or conjugation planning. By keeping the side-chain oxygen protected as a benzyl ether during peptide assembly, the reagent helps reduce variability in side reactions and supports consistent downstream processing for threonine-dependent chemistry.
4. Pharmaceutical Intermediate Peptide Fragments
Boc-O-benzyl-L-Threonine is also used in the manufacture and development of protected peptide intermediates for pharmaceutical research, where threonine-containing fragments are prepared as defined synthetic units for later coupling into larger candidates. Intermediate synthesis groups value the protected amino acid form because it provides a stable, isolable building block that carries both backbone and side-chain protection into the fragment stage, simplifying inventory management and step scheduling. This approach is common in medicinal chemistry supply chains that require reproducible peptide fragment quality for iterative structure-activity relationship work and controlled assembly of multi-residue constructs.
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