H-L-MeSer-OH is a free, naturally derived amino acid derivative featuring an L-configured α-amino acid backbone bearing a methyl-substituted serine side chain (MeSer) and a carboxylic acid group. The molecule contains both an amino functional group and a carboxyl functional group, with the side-chain hydroxyl preserved for hydrogen-bonding and potential derivatization, while the "H-" and "-OH" termini indicate the unprotected N- and C-ends. H-L-MeSer-OH is used as a substrate-like building block in peptide and amino acid derivative synthesis and in chemical biology workflows that require a methylated serine residue for structure-activity studies, labeling, or preparation of more complex MeSer-containing peptides.
CAT No: CP25655
CAS No:2480-26-4
Synonyms/Alias:N-Methyl-L-serine;2480-26-4;(S)-3-Hydroxy-2-(methylamino)propanoicacid;L-Serine,N-methyl-;Serine,N-methyl-,L-;UNII-B6423FC3I2;methylserine;Aquaserine;N-Methylserine;H-Meser-OH;Serine,N-methyl-;N-MethylCL-Serine;L-Serine,N-methyl;AmbotzHAA1218;N-Me-Ser-OH;N-Methyl-(S)-serine;H-N-Me-Ser-OH.HCl;H-L-MESER-OHHCL;SCHEMBL163350;CTK0J8451;MolPort-008-267-986;PSFABYLDRXJYID-VKHMYHEASA-N;B6423FC3I2;ACT06579;ZINC2384916
Chemical Name:N-alpha-Methyl-L-serine
L-Homoserine methyl ester hydrochloride (H-L-MeSer-OH) is an amino acid derivative featuring an L-configured chiral center and a side chain bearing a hydroxyl functionality, enabling hydrogen-bonding interactions and controlled polarity in peptide and small-molecule contexts. The molecule contains a free carboxylic acid (OH) and a primary amino group consistent with amino acid building-block behavior, while the methyl-substituted serine motif (MeSer) supports downstream derivatization at the side chain and stereodefined incorporation into peptide sequences. The stereochemical fidelity of the L-amino acid framework supports predictable coupling stereochemistry and minimizes epimerization risk under standard peptide coupling conditions when appropriate bases and activation chemistries are selected. The hydroxyl-bearing side chain can be protected and later selectively functionalized, making the compound a practical chiral intermediate for amino acid derivatization, peptide building block preparation, and functional group transformation.
1. Peptide Synthesis
L-Homoserine methyl ester hydrochloride (H-L-MeSer-OH) is used in peptide synthesis workflows where a protected or activated amino acid residue is required to introduce a methylated serine-like side chain into linear peptides. The amino and carboxyl groups participate in standard N-to-C peptide coupling logic, while the side-chain hydroxyl enables orthogonal protection strategies to control which functional group reacts during stepwise assembly. Side-chain protection and subsequent deprotection can be coordinated to preserve the L stereocenter and to allow selective modification of hydroxyl-containing peptide analogs. Incorporation of H-L-MeSer-OH into peptide building blocks supports the preparation of peptide libraries and sequence-defined analogs for structure-activity relationship studies and biochemical probe development.
2. Side-Chain Functionalization
L-Homoserine methyl ester hydrochloride (H-L-MeSer-OH) fits side-chain functionalization programs in synthetic organic chemistry because the methyl-substituted hydroxyl group can be converted into leaving groups, ether/ester derivatives, or targeted electrophiles for further coupling. The presence of a free carboxylic acid and amino functionality supports conversion into protected intermediates when selective chemistry at the side chain is required, such as installing orthogonal protecting groups prior to hydroxyl transformation. The chiral amino acid framework helps maintain stereochemical integrity through derivatization steps, supporting downstream formation of stereodefined conjugates and peptidomimetic fragments. Functionalized derivatives derived from H-L-MeSer-OH can then be used to generate analog series for molecular recognition studies and to support iterative medicinal chemistry campaigns focused on side-chain chemistry.
3. Chemical Biology Probes
L-Homoserine methyl ester hydrochloride (H-L-MeSer-OH) serves chemical biology and biomolecule modification efforts where hydroxyl-bearing, chiral amino acid motifs are incorporated into labeling handles or recognition elements. The amino acid backbone can be assembled into peptide or peptidomimetic scaffolds that present the side-chain hydroxyl at defined spatial positions, supporting hydrogen-bonding and controlled reactivity toward conjugation chemistries. Protecting-group strategies that temporarily mask the amino or carboxyl functionality can enable orthogonal installation of functional groups used for affinity tags, imaging probes, or pull-down reagents. Downstream use of H-L-MeSer-OH-derived constructs supports mechanistic studies of protein interactions and substrate recognition in systems where stereochemistry and side-chain polarity influence binding.
4. Process Chemistry Intermediate
L-Homoserine methyl ester hydrochloride (H-L-MeSer-OH) can be applied as a chiral amino acid intermediate in process chemistry and specialty chemical production, where consistent stereochemical supply is required for downstream peptide building block manufacturing. The compound's amino acid functionality supports conversion into activated forms or protected derivatives that align with scalable peptide coupling and intermediate isolation logic, while the hydroxyl side chain enables controlled derivatization routes for further transformation. The L stereocenter and functional group set allow route design that balances protection/deprotection steps with selective side-chain modification, which is a common requirement in industrial amino acid derivative synthesis. H-L-MeSer-OH is therefore suitable for integration into manufacturing sequences that generate protected amino acid derivatives, functionalized intermediates, and stereodefined components for fine chemical synthesis.
5. Analytical Standards
L-Homoserine methyl ester hydrochloride (H-L-MeSer-OH) is applicable to analytical research as a stereochemically defined amino acid reference material for method development and quality control in amino acid and peptide analysis. The combination of amino acid backbone and methylated serine-like side chain provides characteristic chromatographic and spectrometric signatures that can assist in identifying and quantifying related amino acid derivatives, peptide fragments, or derivatized standards. The free carboxylic acid and hydroxyl functionality support derivatization workflows used to enhance detectability, enabling consistent calibration and validation of analytical methods. Use of H-L-MeSer-OH in analytical standard preparation supports reliable monitoring of stereochemical integrity and functional group conversion during peptide building block synthesis and downstream intermediate production.
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