Fmoc-D-Ser(BSi)-OH is an Fmoc-protected D-serine derivative bearing a BSi (tert-butyldimethylsilyl) ether protecting group on the side-chain hydroxyl, classifying it as a protected amino acid used for peptide synthesis. The molecule contains both an Fmoc carbamate-protected amino group and a free carboxylic acid, while the serine side chain is masked as a silyl ether to control chemoselectivity during coupling steps and to modulate side-chain reactivity. In synthetic peptide workflows, it functions as a stepwise-building block that enables incorporation of a protected serine residue with orthogonal side-chain protection for later deprotection and subsequent functionalization or structure-activity studies.
CAT No: CP26695
CAS No:201210-25-5
Synonyms/Alias:Fmoc-D-Ser(BSi)-OH;AKOS015909626;ZINC198363696;I14-32630;201210-25-5
Fmoc-D-Ser(BSi)-OH is an Fmoc-protected D-serine derivative bearing a side-chain silyl protecting group (BSi) on the hydroxymethyl functionality, yielding a chiral amino acid building block with orthogonal protection. The molecule contains an N-Fmoc carbamate that supports base-stable handling during peptide assembly, while the D-configuration at the α-carbon provides defined stereochemistry for incorporation into peptides and peptide-like structures. The side-chain BSi silyl ether masks the serine alcohol, modulating nucleophilicity and preventing premature side reactions during coupling and deprotection sequences. The combined protection pattern makes the compound suitable for controlled side-chain unmasking and downstream derivatization while maintaining compatibility with standard peptide synthesis chemistries.
1. Peptide Synthesis
Fmoc-D-Ser(BSi)-OH is applied in peptide building and solid-phase peptide synthesis where orthogonal protection is required for serine side-chain control. The N-Fmoc carbamate enables stepwise N-terminal deprotection under basic conditions, while the BSi-protected hydroxyl suppresses side-chain participation during amide bond formation. The D-serine stereocenter supports incorporation of non-proteinogenic motifs that can influence peptide conformation, protease resistance, and binding properties in structure-activity relationship studies. The masked serine alcohol can be selectively revealed later to generate a reactive handle for phosphorylation mimics, glycosylation, or ester formation, supporting systematic peptide analog construction.
2. Amino Acid Derivatization
Fmoc-D-Ser(BSi)-OH serves as a chiral intermediate for amino acid derivatization strategies targeting controlled functional group exposure. The protected alcohol functionality allows selective transformations at the side chain after deprotection, enabling conversion to activated esters, carbonate derivatives, or ether-linked substituents for library synthesis. The Fmoc group provides a stable handle for sequential chemistry, allowing side-chain modification without disrupting the amino terminus during intermediate preparation. Downstream use includes generating serine-based chiral fragments for peptidomimetic construction and for producing defined stereochemical standards used in synthetic method development and analytical studies.
3. Bioconjugation Chemistry
Fmoc-D-Ser(BSi)-OH is suitable for chemical biology workflows that require serine-derived conjugation points with controlled reactivity. The D-serine backbone and masked side-chain hydroxyl can be introduced into peptide scaffolds that function as linkers for biomolecule labeling, affinity probes, or immobilization handles. The orthogonal protection pattern supports staged deprotection, so side-chain unmasking can be synchronized with conjugation steps to minimize cross-reactivity from free hydroxyl groups. The resulting D-serine-containing conjugates can be further functionalized into ester or ether linkages, supporting downstream generation of well-defined bioconjugation reagents and research intermediates for biomolecule modification.
4. Peptidomimetics And SAR Studies
Fmoc-D-Ser(BSi)-OH is used in peptidomimetic and SAR studies where stereochemical control and side-chain programmability are central to scaffold design. The D-configuration and serine side-chain enable incorporation of hydroxyl-bearing motifs that can be converted into phosphorylation mimics, hydrogen-bonding variants, or sterically tuned substituents after side-chain deprotection. The Fmoc-protected amino group supports assembly of analog series with consistent N-terminal protection logic, facilitating parallel synthesis of structure-defined libraries. The ability to unmask and derivatize the serine alcohol supports systematic exploration of how hydroxyl geometry and substitution patterns influence molecular recognition in medicinal chemistry and biochemical research.
5. Pharmaceutical Intermediate Preparation
Fmoc-D-Ser(BSi)-OH is employed as a protected amino acid intermediate for manufacturing-oriented synthesis of peptide-related building blocks and process intermediates. The N-Fmoc protection provides a robust strategy for handling and coupling logic in multi-step routes, while the BSi side-chain protection helps manage chemoselectivity by suppressing premature hydroxyl reactivity. The chiral amino acid format supports preparation of D-serine-containing fragments used in downstream assembly of peptide analogs, including intermediates for further functional group installation. The compound's protection scheme aligns with industrially relevant synthesis planning where orthogonal deprotection and controlled side-chain activation are required to maintain stereochemical integrity through successive manufacturing steps.
6. Analytical Research Standards
Fmoc-D-Ser(BSi)-OH can be used to prepare analytical reference materials and method-development substrates for studies involving D-serine-containing peptides and serine side-chain chemistry. The defined stereochemistry and protected functional groups allow synthesis of peptide standards with predictable deprotection behavior and side-chain derivatization outcomes, supporting reliable LC-MS or HPLC characterization workflows. The Fmoc and BSi groups provide a controlled pathway to generate consistent derivatives for quantitation, identity confirmation, or stability assessments of protected and deprotected forms. The resulting reference compounds support analytical research that tracks peptide coupling performance, deprotection selectivity, and side-chain functional group transformations in peptide science.
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