D-Serine benzyl ester hydrochloride

D-Serine benzyl ester hydrochloride is a D-configuration serine derivative in which the amino acid carboxyl group is masked as a benzyl ester and the amino functionality is present as a hydrochloride salt, yielding a stable chiral amino acid ester building block. The molecule contains a stereogenic center at the serine backbone, a primary hydroxymethyl side chain, and an ester-linked carboxylate that participates in acyl transfer chemistry after activation. The benzyl ester can be selectively removed under hydrogenolysis-compatible conditions, while the HCl salt form supports handling and controlled reactivity during peptide coupling and downstream functional group transformations. This protected amino acid ester is commonly used as a chiral intermediate for preparing D-serine-containing fragments, including N- and C-terminally modified derivatives relevant to peptide chemistry and structure-guided synthesis.

1. Protected Peptide Building Block

D-Serine benzyl ester hydrochloride is used in peptide synthesis workflows where a protected amino acid ester is required for controlled coupling and later C-terminal unmasking. The benzyl ester protects the carboxyl group during amide bond formation, while the D-configuration preserves stereochemical integrity of the serine residue. The side-chain hydroxyl enables orthogonal protection strategies (such as conversion to an O-protected serine derivative) to prevent undesired esterification or side reactions during chain assembly. Downstream deprotection can regenerate the free carboxylate and hydroxyl functionality for incorporation into D-serine-containing peptides, peptidomimetics, and sequence-defined analog libraries, supporting both research-scale synthesis and route design for industrial peptide intermediates.

2. Side-Chain Hydroxymethyl Functionalization

D-Serine benzyl ester hydrochloride serves as a starting chiral amino acid intermediate for side-chain functionalization targeting the serine hydroxymethyl group. The primary alcohol can be transformed into reactive handles for derivatization, including conversion to protected hydroxyl forms for orthogonal synthesis or activation to enable further substitution chemistry. The preserved D-stereocenter allows stereochemically consistent generation of serine-derived motifs used in chemical biology probes and amino acid modification studies. Resulting derivatives can be carried into peptide analog construction, conjugation-ready intermediates, or polymerizable monomers where the alcohol functionality is required for controlled attachment and subsequent downstream elaboration.

3. Bioconjugation And Chemical Biology

D-Serine benzyl ester hydrochloride is applicable to chemical biology and bioconjugation efforts that require a D-serine residue embedded in a chemically addressable scaffold. The amino acid backbone provides a defined stereochemical element, while the benzyl ester and hydroxyl group enable stepwise protection/deprotection sequences to match conjugation timing and chemoselectivity. The hydrochloride salt form can facilitate handling in coupling and intermediate preparation steps that lead to D-serine-bearing linkers, affinity tags, or substrate analogs used in biomolecular interaction studies. Generated conjugation-ready fragments can be incorporated into larger constructs such as labeled peptides, immobilized ligands, or probe libraries used for studying biomolecular recognition and enzyme tolerance toward stereodefined serine motifs.

4. Chiral Intermediate For SAR Studies

D-Serine benzyl ester hydrochloride is suitable for structure-activity relationship studies requiring stereochemically defined serine-containing fragments and systematic functional modification. The D-stereochemistry at the serine backbone supports SAR designs that differentiate stereoisomer effects in peptide-like scaffolds and constrained peptidomimetics. The benzyl ester functions as a protected carboxyl handle that can be converted into activated acyl forms for fragment coupling, while the side-chain hydroxyl can be varied through protection level or derivatization to tune polarity and hydrogen-bonding patterns. Downstream products from this intermediate can be assembled into analog series for medicinal chemistry research and for manufacturing-oriented intermediate preparation where consistent stereochemical identity is required across batches.

5. Pharmaceutical Intermediate Preparation

D-Serine benzyl ester hydrochloride is used as a chiral intermediate in pharmaceutical manufacturing chains that require protected amino acid esters for controlled synthesis of D-serine-containing building blocks. The benzyl ester offers a removable C-terminal protection strategy compatible with manufacturing-friendly deprotection logic, enabling conversion to free carboxylic acids or activated derivatives for subsequent coupling steps. The serine hydroxymethyl group can be managed through orthogonal protection schemes to control chemoselectivity during multistep assembly of peptide fragments or peptide-derived intermediates. Downstream elaboration can yield standardized intermediates for fine chemical production, including peptide coupling partners, stereodefined amino acid derivatives, and process-ready materials for generating larger active or investigational scaffolds in an industrial setting.

1. Extended exenatide administration enhances lipid metabolism and exacerbates pancreatic injury in mice on a high fat, high carbohydrate diet

2. C-Peptide replacement therapy and sensory nerve function in type 1 diabetic neuropathy

3. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes

4. High fat diet and GLP-1 drugs induce pancreatic injury in mice

5. Effect of Probiotic Lactobacillus plantarum on Streptococcus mutans and Candida albicans Clinical Isolates from Children with Early Childhood Caries