Boc-O-benzyl-L-threonineN-hydroxysuccinimideester is a protected, derivatized threonine amino acid derivative in which the amino group is masked as a Boc carbamate and the side-chain hydroxyl is protected as a benzyl ether, while the carboxyl functionality is converted into an N-hydroxysuccinimide (NHS) ester. The molecule contains both a Boc-protected α-amino group and a benzyl-protected β-hydroxyl-bearing side chain, and it bears an NHS-activated carboxyl group that retains the L-threonine stereochemical designation implied by the name. In synthesis and bioconjugation workflows, the NHS ester provides a handle for coupling to nucleophiles such as primary amines under aqueous conditions, while the protecting groups support chemoselective handling of the amino and side-chain alcohol during preparation of threonine-containing peptide or conjugate building blocks.
CAT No: CP01912
CAS No:32886-43-4
Synonyms/Alias:Boc-Thr(Bzl)-OSu;32886-43-4;ST51037521;Boc-O-benzyl-L-threoninehydroxysuccinimideester;BOC-THR-OSU;Boc-Threonine(BZL)-OSU;15082_ALDRICH;SCHEMBL9636231;15082_FLUKA;MolPort-003-926-636;C20H26N2O7;6447AH;ZINC71788010;AKOS024386373;K-7607;N-(tert-Butoxycarbonyl)-O-benzyl-L-threoninesuccinimidylester;2,5-dioxoazolidinyl(2S,3R)-2-[(tert-butoxy)carbonylamino]-3-(phenylmethoxy)butanoate
Boc-O-benzyl-L-threonineN-hydroxysuccinimideester is a Boc-protected L-threonine derivative bearing an O-benzyl side-chain protecting group and an N-hydroxysuccinimide ester functionality on the amino terminus. This combination makes the reagent a stable, activated amino-acid building block for forming amide bonds under standard peptide and bioconjugation coupling conditions, while the Boc and O-benzyl groups provide orthogonal protection during downstream assembly. Researchers use this type of activated threonine intermediate to introduce a protected threonine residue with controlled stereochemistry into peptide segments and to generate threonine-containing conjugates with defined substitution patterns.
1. Peptide Segment Coupling
Boc-O-benzyl-L-threonineN-hydroxysuccinimideester is used in peptide synthesis workflows where an activated amino-acid derivative is preferred for efficient amide bond formation during segment coupling or late-stage assembly. Peptide chemists commonly incorporate this reagent to build threonine-containing sequences while maintaining the L-configuration and preserving side-chain protection through the O-benzyl group. The N-hydroxysuccinimide ester activation supports straightforward coupling to amine-bearing partners, helping streamline the preparation of protected peptide intermediates used in custom peptide manufacturing and research-grade peptide libraries.
2. Threonine-Containing Bioconjugates
Boc-O-benzyl-L-threonineN-hydroxysuccinimideester is also applied as an activated threonine building block for preparing threonine-functional bioconjugates where an NHS ester is leveraged for amine-reactive coupling. Chemical biology and protein chemistry teams use it to introduce a protected threonine unit into conjugation schemes that require controlled handling of the amino-acid functionality and retention of side-chain protection during synthesis. This reagent is particularly relevant when downstream processing will occur after conjugate formation, benefiting from the Boc and O-benzyl groups as stability elements during the coupling-to-conjugate workflow.
3. Protected Amino Acid Intermediate Synthesis
Boc-O-benzyl-L-threonineN-hydroxysuccinimideester serves as a practical intermediate for constructing protected threonine derivatives and peptide-ready fragments used in pharmaceutical intermediate development. Process and development chemists select this activated form when they need reliable conversion of an amino-acid unit into an amide-linked intermediate without requiring pre-activation by separate coupling reagents at the point of use. The presence of Boc on the nitrogen and O-benzyl on the side-chain supports downstream orthogonal deprotection strategies, enabling controlled elaboration into larger protected building blocks for research-scale synthesis and specialty chemical manufacturing.
4. Amino-Acid Derivative Library Preparation
Boc-O-benzyl-L-threonineN-hydroxysuccinimideester is used in parallel synthesis and library-building efforts where a consistent, activated threonine reagent is valuable for generating a set of threonine-containing amide products with defined protection patterns. Medicinal chemistry and chemical biology groups often rely on such activated amino-acid intermediates to rapidly access protected analogs that can later be deprotected or further functionalized for structure-property studies. The NHS ester activation supports uniform coupling to a range of amine-containing building blocks, while the Boc and O-benzyl groups help maintain the integrity of the threonine side-chain during the library generation phase.
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