Boc-D-Ser(Bzl)-OH

Chemical properties

White crystalline powder

The Uses of Boc-D-Ser(Bzl)-OH

N-BOC-O-Benzyl-D-serine, is an amino acid derivative used in chemical synthesis and peptide chemistry.is used in preparation of substituted naphthyl thiadiazolidinones as protein tyrosine phosphatase degraders for treating cancer and metabolic diseases.

Biological Activity

Boc-O-benzyl-D-serine is an inhibitor of the uptake of galactose and its derivatives. It has potent inhibitory activity against the uptake of galactose, glucose, and lactose. This drug is also effective in inhibiting the uptake of tetrazole, a substance that inhibits glycolysis. Boc-O-benzyl-D-serine is able to inhibit atherosclerotic lesions caused by piperidine, which has been shown to be synthesized from benzyl alcohol and piperidine. The oral administration of this compound can enhance fibroblast cells that are resistant to insulin.

Synthesis

N-Boc D-Se (500 mg, 2.43 mmol) dissolved in anhydrous DMF (4 mL) was slowly added to a dispersion of 60% NaH (204 mg, 5.1 mmol) in anhydrous DMF at 0 ° C. Stir the mixture at room temperature for 1 hour and cool to 0 ° C. Subsequently, benzyl bromide (0.29 mL, 2.43 mmol) was added and the mixture was heated to room temperature. After 4 hours of reaction, add saturated NH4Cl (1 mL) to quench the reaction. Finally, the product Boc-D-Ser(Bzl)-OH was obtained through purification.