Fmoc-Ser(tBu)-ODhbt is an Fmoc-protected serine derivative bearing a tert-butyl-protected side-chain hydroxyl and an ODhbt ester functionality on the serine oxygen, placing it in the class of protected amino acid building blocks for peptide synthesis. The molecule contains an Fmoc carbamate at the amino group and a carboxyl group as an ODhbt-protected form, with the serine side chain presenting a tert-butyl-protected alcohol that modulates chemoselectivity during coupling and subsequent deprotection steps. In solid-phase or solution-phase peptide assembly, this protected analogue is used to control reactivity of the hydroxyl and carboxyl functionalities while enabling stepwise incorporation of a serine residue into peptide intermediates and supporting the preparation of more complex, selectively functionalized peptide derivatives.
CAT No: CP26185
CAS No:109434-27-7
Synonyms/Alias:Fmoc-Ser(tBu)-ODhbt;109434-27-7;Fmoc-O-tert-butyl-L-serine3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylester;Fmoc-O-tert-butyl-D-serine3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazineester;201210-27-7;F0148_SIGMA;47455_FLUKA;CTK8E9972;6989AH;ZINC71788091;RT-013024;Fmoc-O-tert-Butyl-L-serine3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylester
Fmoc-Ser(tBu)-ODhbt is an Fmoc-protected serine derivative in which the side-chain hydroxyl is masked as a ODhbt ester, while the amino group is protected as the stable Fmoc carbamate. The molecule contains a chiral serine center, a benzyl-like aromatic Fmoc chromophore for solid-phase peptide synthesis monitoring, and an O-ester functional handle that modulates side-chain reactivity during coupling and subsequent transformations. The ODhbt group is designed to withstand typical peptide coupling conditions yet can be removed or converted under orthogonal deprotection strategies, enabling controlled exposure of the serine hydroxyl for downstream chemistry. The presence of both a protected amine and a protected side-chain oxygen makes the compound a practical chiral building block for peptide construction, serine-based functionalization, and protected-amino-acid intermediate preparation.
1. Protected Amino Acid Chemistry
Fmoc-Ser(tBu)-ODhbt supports protected amino acid synthesis workflows by combining an Fmoc carbamate on the α-amino group with an orthogonally protected serine side-chain oxygen. The serine ODhbt ester and the Fmoc group together provide a protected state that can be carried through activation/coupling steps without premature side-chain participation. Orthogonal deprotection can be applied to selectively unmask the serine hydroxyl after peptide assembly, enabling targeted side-chain derivatization or incorporation into functional peptide analogs. Downstream, the compound functions as a chiral intermediate for preparing serine-containing building blocks used in fine chemical synthesis and peptide chemistry.
2. Peptide Synthesis
Fmoc-Ser(tBu)-ODhbt is suited for peptide building block preparation in Fmoc-based solid-phase peptide synthesis and controlled solution-phase coupling. The Fmoc-protected amino group enables standard base-mediated Fmoc removal to generate a reactive N-terminus for peptide bond formation, while the ODhbt ester protects the side-chain hydroxyl from acylation, oxidation, or undesired hydrogen-bonding during coupling. The serine stereocenter is preserved through the synthesis sequence, supporting stereochemically defined peptide frameworks and consistent side-chain positioning in SAR studies. After peptide assembly, selective unmasking of the serine hydroxyl can enable phosphorylation mimics, ester/amide formation, or conjugation handles for further molecular modification.
3. Side-Chain Functionalization
Fmoc-Ser(tBu)-ODhbt enables side-chain functionalization strategies where controlled access to the serine hydroxyl is required after assembly or during intermediate synthesis. The protected hydroxyl as an ODhbt ester provides a chemically defined oxygen functionality that can be converted into reactive alcohol equivalents under orthogonal conditions, supporting subsequent formation of esters, ethers, or linkage points for biomolecule conjugation. The combination of Fmoc and ODhbt protection supports sequential protection/deprotection logic, reducing cross-reactivity between the α-amino protecting group and the side-chain oxygen. Resulting derivatives can serve as intermediates for peptidomimetic construction, chemical biology probes, and structure-activity relationship studies that depend on precise serine side-chain chemistry.
4. Chemical Biology Probes
Fmoc-Ser(tBu)-ODhbt can be applied to chemical biology workflows that require serine-containing peptide probes with controlled reactive-group exposure. The Fmoc-protected backbone supports incorporation into peptide scaffolds, while the protected serine oxygen can be unmasked to install functional moieties for labeling, affinity capture, or controlled reactivity in assay development. The chiral serine center and protected oxygen placement help maintain defined stereochemistry and hydrogen-bonding patterns that influence molecular recognition by enzymes, receptors, or binding domains. Downstream probe generation can include conjugation-ready intermediates and peptide-based reagents for mechanistic studies of amino acid recognition and post-translational modification mimicry.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-Ser(tBu)-ODhbt may serve as a manufacturing intermediate in the preparation of serine-rich peptide intermediates used in pharmaceutical process chemistry and specialty fine chemical production. The Fmoc protection strategy aligns with scalable peptide synthesis routes, while the ODhbt side-chain protection supports process robustness by minimizing side reactions from the serine hydroxyl during repeated coupling and washing cycles. Orthogonal deprotection enables controlled downstream processing steps to generate defined serine-functional products without altering the peptide backbone stereochemistry. The resulting serine-containing intermediates can be used to produce peptide analogs, process-compatible building blocks, and downstream derivatives that require predictable functional group handling.
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