H-D-Ser-OMe*HCl

H-D-Ser-OMe*HCl is a protected amino acid derivative featuring the D-configuration at the serine stereocenter and a methyl ester hydrochloride salt form, with the side-chain hydroxymethyl group remaining unprotected for direct functional-group chemistry. The molecule combines an amino functionality in a hydrochloride-associated form with an ester carbonyl that can participate in peptide coupling after conversion to an activated acid or after ester manipulation. The presence of the free side-chain alcohol enables selective side-chain derivatization while maintaining a defined chiral scaffold for stereochemical studies. The D-Ser methyl ester salt behavior supports controlled downstream transformations that are compatible with protected amino acid synthesis workflows and chiral intermediate preparation.

1. Peptide Synthesis

H-D-Ser-OMe*HCl supports peptide construction workflows where D-serine is required at a specific position, leveraging the amino acid backbone geometry and the ester functionality as a handle for C-terminal activation or conversion. The side-chain hydroxyl group can be managed through protection strategies during coupling, enabling orthogonal chemistries when assembling peptides by amide bond formation. The D-stereocenter provides stereochemical fidelity for peptide analogs used in structure-function investigations and sequence-specific synthetic libraries. The resulting intermediates and activated derivatives can be carried into iterative coupling cycles to generate D-serine-containing peptides and peptide fragments.

2. Side-Chain Functionalization

H-D-Ser-OMe*HCl is well suited to side-chain functionalization chemistry because the serine hydroxymethyl group can undergo derivatization to install ethers, esters, or other oxygen-linked substituents while preserving the chiral amino acid core. The methyl ester hydrochloride form facilitates controlled handling of the carboxyl functionality in synthetic sequences that require ester-to-acid or ester-to-activated species conversion. Side-chain-modified D-serine derivatives can be used to probe hydrogen-bonding patterns, polarity changes, and conformational effects in peptidomimetics. Downstream transformations from this scaffold can feed into chemical biology reagents, enzyme substrate analogs, and stereochemically defined building blocks for SAR studies.

3. Chiral Building Block Development

H-D-Ser-OMe*HCl functions as a chiral amino acid intermediate for asymmetric or stereochemically controlled synthesis, where the D-configuration at serine is a defining structural element. The combination of a stereogenic center, a hydroxymethyl side chain, and a methyl ester provides a compact platform for generating protected amino acid derivatives with tailored protection-group strategies for N- and O-functionalities. The hydrochloride salt form can support reproducible salt-based handling and can be incorporated into manufacturing-oriented intermediate preparation routes that require consistent chiral identity. The compound can be converted into other chiral serine building blocks used for fine chemical synthesis, peptide fragment assembly, and downstream stereochemical diversification.

4. Chemical Biology Probes

H-D-Ser-OMe*HCl can be applied in chemical biology research contexts where D-serine-containing motifs are used to tune stability, protease resistance, or binding-site interactions in peptide-like probes. The free side-chain hydroxyl enables conjugation-ready modification to introduce linkers or functional handles, while the amino acid backbone supports incorporation into probe scaffolds through amide linkage formation. The methyl ester and salt form facilitate stepwise conversion into coupling-compatible forms for labeling constructs and molecular recognition studies. The resulting D-serine-based probe intermediates can be used to generate peptide mimics for biochemical assays and mechanistic investigations of biomolecular interactions.

5. Pharmaceutical Intermediate Preparation

H-D-Ser-OMe*HCl is suitable for pharmaceutical intermediate preparation where stereodefined serine derivatives are required as upstream building blocks for peptidomimetic and amino acid-derived motifs. The protected amino acid ester framework supports process-compatible transformations that can lead to activated carboxylic acid derivatives, coupling-ready species, or orthogonally protected N- and O-functional intermediates. The D-configuration and side-chain hydroxymethyl group enable targeted incorporation into larger synthetic sequences that build complex drug-like structures. The compound thereby serves as a chiral precursor for manufacturing routes that require amino acid-based intermediates with controlled functional group reactivity and stereochemical integrity.

1. An interdomain binding site on HIV-1 Nef interacts with PACS-1 and PACS-2 on endosomes to down-regulate MHC-I

2. Effect of Short-Term Desiccation, Recovery Time, and CAPA-PVK Neuropeptide on the Immune System of the Burying Beetle Nicrophorus vespilloides

3. Application of human liver organoids as a patient-derived primary model for HBV infection and related hepatocellular carcinoma

4. Emerging applications of nanotechnology for diagnosis and therapy of disease: a review

5. Cationic cell-penetrating peptides are potent furin inhibitors