Fmoc-Thr(tBu)-ODhbt is an Fmoc-protected threonine derivative bearing a tert-butyl-protected side-chain hydroxyl and an ODhbt ester functionality on the carboxylate, placing it in the class of protected amino acid building blocks for peptide chemistry. The molecule contains an Fmoc carbamate protecting group on the α-amino functionality, a threonine-derived β-hydroxy side chain masked as a tert-butyl ether, and a carboxyl group converted to an ODhbt ester to control chemoselectivity during coupling and minimize undesired side reactions. In synthetic workflows such as solid-phase or solution-phase peptide assembly, this protected analogue is employed as a stepwise amino acid unit that can be incorporated into peptide sequences while the protecting groups regulate reactivity of the amino and hydroxyl functionalities.
CAT No: CP26239
CAS No:119767-84-9
Synonyms/Alias:(2S,3R)-4-Oxobenzo[d][1,2,3]triazin-3(4H)-yl2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)butanoate;119767-84-9;MolPort-035-757-710;AKOS024462391;AK162637
Fmoc-Thr(tBu)-ODhbt is an Fmoc-protected threonine derivative bearing a tert-butyl-protected side-chain hydroxyl and an ODhbt ester functionality, forming a chiral amino acid building block with defined stereochemistry at the α-carbon. The molecule contains an N-fluorenylmethoxycarbonyl (Fmoc) carbamate for base-labile N-protection, a side-chain O-substituent that modulates hydroxyl reactivity, and a carboxylate-equivalent ODhbt group that can participate in downstream activation or coupling-related transformations. The presence of orthogonally addressable protecting elements supports controlled deprotection sequences in peptide synthesis workflows and enables selective functional group manipulation without disturbing the α-amino protection. The combination of protected alcohol character and chiral center makes Fmoc-Thr(tBu)-ODhbt suitable as a stereochemically defined intermediate for peptide construction and for generating further derivatized threonine-containing analogs.
1. Peptide Synthesis
Fmoc-Thr(tBu)-ODhbt is used in peptide building workflows where Fmoc-based N-protection supports standard peptide coupling cycles and orthogonal deprotection strategies. The threonine backbone provides a chiral α-amino acid motif, while the tBu-protected side-chain hydroxyl helps control side-chain reactivity during amide bond formation and minimizes undesired O-acylation or side reactions. The ODhbt functionality can serve as a handle for coupling-related activation or for preparing derivatives that maintain compatibility with protected amino acid chemistry. Incorporation of this chiral threonine unit enables synthesis of peptides and peptide fragments containing protected threonine residues for later side-chain unveiling or selective modification. Downstream peptide analog generation can proceed through controlled deprotection to reveal the side-chain alcohol for further functionalization.
2. Side-Chain Functionalization
Fmoc-Thr(tBu)-ODhbt is applied in side-chain modification strategies targeting threonine-derived functional handles for chemical biology and peptidomimetic construction. The protected hydroxyl character of the tBu group supports selective manipulation by allowing the side-chain oxygen to remain dormant during early synthetic steps, while later deprotection can expose an alcohol for derivatization. The ODhbt-associated functionality provides a chemically addressable oxygen-based group that can be leveraged to access oxygen-linked linkers, conjugation-ready intermediates, or protected derivatives for controlled reactivity. Threonine stereochemistry is retained through the chiral amino acid framework, enabling stereodefined products for structure-activity relationship studies and receptor-binding motif exploration. The resulting threonine-containing derivatives can be converted into further functional molecules that preserve peptide-like geometry and hydrogen-bonding patterns.
3. Chemical Manufacturing Intermediates
Fmoc-Thr(tBu)-ODhbt is suitable for process chemistry intermediate preparation where orthogonally protected amino acid derivatives support scalable, stepwise manufacturing routes. The Fmoc carbamate provides a robust N-protection element that can be removed under base conditions in a controlled manner, enabling predictable sequencing in protected amino acid synthesis and peptide building block manufacture. The combination of sterically protected side-chain hydroxyl (tBu) and oxygen-based ODhbt functionality supports controlled handling of reactive sites during isolation, purification, and downstream conversion to activated coupling forms. The chiral threonine scaffold enables consistent stereochemical outcomes across batches, which is relevant for industrial production of peptide intermediates and fine chemical synthesis. Downstream utility includes conversion into protected threonine units for manufacturing peptide fragments and for producing derivatized amino acid intermediates used in specialty chemical production.
4. Bioconjugation Chemistry
Fmoc-Thr(tBu)-ODhbt is used in bioconjugation-oriented synthesis where threonine residues are incorporated into linker-bearing peptide constructs and conjugation-ready intermediates. The threonine backbone supplies a stereodefined amino acid segment that can be assembled into peptide scaffolds, while the protected side-chain hydroxyl helps maintain stability during assembly prior to conjugation-specific transformations. The ODhbt-associated oxygen functionality can enable preparation of oxygen-reactive or activated derivatives that can be carried forward into conjugation steps after appropriate deprotection or activation. Fmoc protection supports selective N-terminal handling when generating defined peptide conjugates, including fragments used for labeling strategies and biomolecule modification. The resulting threonine-containing conjugation intermediates support downstream formation of stable linkages while maintaining the structural integrity of peptide-like recognition elements.
5. Analytical Research Standards
Fmoc-Thr(tBu)-ODhbt is applicable to analytical research and method development requiring defined, stereochemically characterized threonine-containing standards. The presence of Fmoc and protected functional groups provides distinct chromatographic and spectrometric signatures that can aid in monitoring protected amino acid handling, deprotection progress, and impurity profiling in peptide synthesis workflows. The chiral α-center and protected side-chain oxygen contribute to reproducible retention behavior and allow targeted tracking of threonine-derived species during synthetic sequence optimization. The ODhbt-related oxygen functionality can further support identification of intermediate transformation states when developing LC-MS or related analytical methods for protected amino acid derivatives. Defined standards based on this amino acid building block can be employed to support quality-by-design style characterization for peptide and amino acid intermediate manufacturing.
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