Bzl-L-Ser(Bzl)-OMe*(COOH)2

Bzl-L-Ser(Bzl)-OMe*(COOH)2 is a benzyl-protected L-serine derivative in which the hydroxyl-bearing side chain is protected as a benzyl ether, and the alpha-amino group is benzylated (Bzl), while the alpha-carboxyl functionality is present as a methyl ester (OMe) paired with two carboxylic acid equivalents indicated by *(COOH)2, creating a multi-functional, highly polar chiral amino acid intermediate. The molecule retains the L-configuration at the stereogenic alpha carbon, enabling stereochemically defined peptide bond formation and downstream chiral derivatization. Benzyl protecting groups on nitrogen and oxygen support orthogonal protection strategies under hydrogenolysis, while the carboxyl/ester functionality supports controlled conversion between activated acid forms and peptide coupling-ready species. The combined presence of protected amine, protected hydroxyl, and carboxyl groups makes the compound suitable for iterative amino acid derivatization, protected amino acid synthesis, and building-block preparation for peptide and peptidomimetic chemistry.

1. Protected Amino Acid Synthesis

Bzl-L-Ser(Bzl)-OMe*(COOH)2 supports protected amino acid synthesis workflows where benzyl-protected N and O functionalities help manage side reactions during coupling and activation steps. The L-serine backbone provides a stereodefined alpha-amino and alpha-carboxyl framework, while the benzyl ether on the side-chain hydroxyl controls chemoselectivity for orthogonal transformations. Carboxyl/ester features can be converted into peptide coupling intermediates and then carried through multistep sequences with controlled deprotection, including hydrogenolysis-based removal of benzyl groups to reveal reactive amine and serine hydroxyl for subsequent functionalization. The resulting protected amino acid intermediate can be used to prepare defined peptide building blocks and to generate downstream derivatives that require strict control of serine side-chain chemistry.

2. Peptide Coupling Chemistry

Bzl-L-Ser(Bzl)-OMe*(COOH)2 is suitable for peptide coupling chemistry in synthetic peptide and peptidomimetic assembly where serine residues must be incorporated with protected side-chain functionality. The benzyl-protected serine hydroxyl prevents undesired O-acylation or crosslinking during amide bond formation, while the benzyl-protected amino group aligns with standard peptide synthesis strategies that rely on selective activation of the carboxyl component. The L-configuration at the alpha carbon enables formation of stereochemically consistent peptide bonds, supporting structure-defined peptide analog construction for research-grade libraries. Downstream deprotection can regenerate the serine hydroxyl and amino functionality for further derivatization, enabling iterative chain extension and functional group installation at the serine position.

3. Side-Chain Functionalization

Bzl-L-Ser(Bzl)-OMe*(COOH)2 enables side-chain functionalization programs that exploit the serine hydroxyl as a handle for controlled chemical modification after protecting-group removal. Benzyl protection on the side-chain oxygen allows the intermediate to be handled under conditions that would otherwise risk hydroxyl participation, while hydrogenolysis can expose the free serine alcohol for subsequent esterification, etherification, or phosphorylation-mimetic chemistry. Carboxyl functionalities provide additional sites for conversion into activated acids or for forming salts and conjugation-ready derivatives, supporting downstream molecular modification beyond peptide contexts. The chiral, protected serine scaffold therefore serves as a practical amino acid chemistry intermediate for generating functionalized serine-containing analogs used in biochemical research and synthetic methodology development.

4. Chemical Biology Labeling

Bzl-L-Ser(Bzl)-OMe*(COOH)2 can be applied in chemical biology labeling strategies where serine-containing motifs are needed as defined, stereochemically controlled building blocks for probe synthesis. The protected amino and benzyl-protected hydroxyl groups support stepwise synthesis of conjugatable derivatives without premature reaction of the alcohol functionality, while the carboxyl/ester pattern supports conversion to coupling partners such as activated acids or linkers. Deprotection strategies can reveal functional groups for subsequent attachment to biomolecule-reactive handles or for incorporation into peptide-based probes that require controlled serine chemistry. The resulting labeled or conjugation-ready intermediates align with amino acid derivatization and biomolecule modification workflows that depend on precise functional group placement and stereochemical fidelity.

5. Process Chemistry Intermediate

Bzl-L-Ser(Bzl)-OMe*(COOH)2 is relevant to process chemistry intermediate preparation where benzyl protecting groups provide robust protection during scale-up-compatible coupling and purification operations. The presence of protected N and O functionalities supports chemoselective transformations by minimizing side reactions associated with free amine and serine hydroxyl, while the L-amino acid framework allows predictable conversion between ester/acid forms used to design manufacturing routes. Carboxyl/ester functionality can be managed through activation and controlled deprotection steps, enabling consistent generation of peptide-building-block precursors and downstream functionalized amino acid derivatives. The compound's defined stereochemistry and protection pattern make it suitable for industrial fine chemical synthesis and for producing serine-based intermediates used in peptide manufacturing supply chains.

1. Tachykinin-related peptides modulate immune-gene expression in the mealworm beetle Tenebrio molitor L

2. A possible role of tachykinin-related peptide on an immune system activity of mealworm beetle, Tenebrio molitor L

3. Myotropic activity of allatostatins in tenebrionid beetles

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

5. P-selectin and Complement’s Role in a Neonatal Model of Germinal Matrix Hemorrhage-Induced Secondary Injury