Fmoc-L-Hse(Me)-OH is an Fmoc-protected L-amino acid derivative bearing a heterocyclic side chain characteristic of homoselenoamino acids and a methyl substituent on the side-chain selenium-containing moiety. The molecule contains an Fmoc carbamate protecting group on the amino functionality and a free carboxylic acid, with the side chain presenting a selenium-centered functionality that can influence polarity and redox/coordination behavior in peptide environments. In peptide chemistry and chemical biology, it is used as a building block for incorporating this modified amino acid residue into protected peptide intermediates and for preparing selenium-containing peptide analogues used in structure-activity studies, labeling strategies, or analytical method development.
CAT No: CP25462
CAS No:173212-86-7
Synonyms/Alias:173212-86-7;Fmoc-hse(me)-oh;Fmoc-O-methyl-L-homoserine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-methoxybutanoic acid;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methoxybutanoic acid;MFCD00270543;Fmoc-O-Methyl-L-Homoseri;(2S)-2-{[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO}-4-METHOXYBUTANOIC ACID;JBIRUWVMQYLPPX-SFHVURJKSA-N;N-Fmoc-O-methyl-L-homoserine;SCHEMBL621563;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-methoxybutanoic acid;L-Homoserine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-methyl-;AKOS022184289;BS-27490;CS-0137333;E70531;S-173212-86-7;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-methyl-L-homoserine;(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methoxy-butyric acid;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-methoxybutanoic acid;N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-methyl-L-homoserine (Fmoc-L-Hse(Me)-OH);
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-methyl-L-homoserine, Fmoc-L-methoxinine
Fmoc-L-Hse(Me)-OH is an Fmoc-protected L-amino acid derivative in which the side chain is based on homoserine with an additional methyl substituent, giving a chiral, stereochemically defined amino acid building block. The molecule contains an Fmoc carbamate on the alpha-amino group, a free carboxylic acid for coupling chemistry, and a side-chain hydroxyl functionality that can participate in hydrogen bonding and selective derivatization. The presence of the secondary methylated side chain can influence steric profile and conformational preferences during peptide bond formation and subsequent transformations. As a chiral protected amino acid intermediate, it is designed to undergo standard peptide coupling after orthogonal deprotection of the Fmoc group and can be converted into downstream functionalized derivatives through side-chain hydroxyl chemistry.
1. Peptide Synthesis
Fmoc-L-Hse(Me)-OH is used in peptide building workflows where Fmoc deprotection enables controlled N-terminal exposure for stepwise amide bond formation. The combination of an Fmoc-protected alpha-amino group and a free carboxylic acid supports compatibility with common peptide coupling strategies, while the side-chain hydroxyl provides a handle for orthogonal protection or post-coupling modification. The methylated homoserine side chain can be incorporated into peptide sequences to tune sterics, solvation, and local backbone/side-chain orientation. Downstream, the resulting peptides can serve as substrates or analogs in biochemical assays and as scaffold components in peptidomimetic design.
2. Side-Chain Functionalization
Fmoc-L-Hse(Me)-OH is suitable for amino acid derivatization programs targeting side-chain hydroxyl chemistry, including conversion to protected alcohol derivatives or functional handles for further synthetic elaboration. The methyl-substituted homoserine side chain bears a stereodefined hydroxyl that can be selectively protected, oxidized, or transformed into leaving-group equivalents depending on the orthogonal protection scheme chosen for the peptide or intermediate stage. Fmoc protection on the alpha-amine allows side-chain modifications to be planned either before or after incorporation into a peptide, supporting route design for complex targets. Functionalized derivatives derived from this building block can be used to generate libraries of amino acid analogs for structure-activity relationship studies and molecular recognition investigations.
3. Chemical Biology Probes
Fmoc-L-Hse(Me)-OH is applied in chemical biology research where amino acid incorporation into peptides enables controlled presentation of reactive oxygen-containing side chains for labeling and probe construction. The defined L-configuration and methylated side chain can affect reactivity and conformational behavior of the resulting biomolecular conjugates, which is relevant when designing probes that require specific spatial arrangement. Fmoc-based peptide assembly supports integration into longer sequences that can be used as recognition elements, affinity handles, or enzyme-interaction motifs. Downstream conjugation strategies can leverage the side-chain hydroxyl as a functional anchor for further derivatization into tagged or immobilizable chemical biology reagents.
4. Peptidomimetics And SAR
Fmoc-L-Hse(Me)-OH serves as a chiral intermediate for peptidomimetic construction and structure-activity relationship studies that require controlled modification of side-chain topology. The methylated homoserine motif provides a distinct steric and hydrogen-bonding pattern compared with unsubstituted analogs, enabling systematic comparison of analog series during SAR investigations. Fmoc protection supports consistent peptide coupling during synthesis of analog panels, while the free carboxyl group enables incorporation as a defined residue in sequence-defined constructs. Resulting peptide analogs and constrained variants can be used to map how side-chain substitution and hydroxyl presence influence binding or processing in biochemical systems.
5. Pharmaceutical Intermediate Preparation
Fmoc-L-Hse(Me)-OH is utilized in process chemistry and fine chemical synthesis as a protected amino acid intermediate for manufacturing peptide-based intermediates and related functional building blocks. The Fmoc carbamate and free carboxylic acid combination supports scalable synthetic planning for downstream peptide coupling, including integration into protected peptide fragments and intermediate stages of larger synthetic sequences. The stereodefined L-amino acid framework and hydroxyl-bearing side chain can be carried through orthogonal protection and deprotection steps to meet sequence-specific requirements in industrial peptide manufacturing. Downstream, the compound can be converted into protected residue forms and subsequently incorporated into peptide intermediates used for specialty chemical production and applied product development.
6. Analytical Standards
Fmoc-L-Hse(Me)-OH is suitable for analytical research and method development where a defined, stereochemically pure amino acid derivative is needed as a reference for chromatographic identification and mass spectrometric characterization. The Fmoc group provides a strong, distinctive tag that can improve detectability and facilitate consistent behavior in LC-MS workflows, while the methylated homoserine side chain and free carboxyl group contribute characteristic fragmentation patterns. The compound can be used to validate derivatization or deprotection steps during peptide analysis, including monitoring of Fmoc removal and assessment of residue incorporation. Downstream, this enables reliable interpretation of synthetic mixtures and supports quality-focused characterization of amino acid derivative and peptide building block preparations.
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