Benzyl glycinate hydrochloride

White Solid

Potent crosslinking inhibitors.

The benzyl ester group of the amino acid monomers promote kinetically controlled synthesis (KCS) of polypeptides by increasing the substrate affinity and specificity of the enzyme. It is useful in the chemoenzymatic polymerization of glycine monomers.

N-Boc glycine (2.85 mmol), benzyl alcohol (2.85 mmol), 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.71 mmol) and DMAP (0.6 mmol) were reacted in dichloromethane at 25 C with stirring overnight. At the end of the reaction the reaction mixture was extracted with ethyl acetate and the resulting organic layer was washed with brine. The organic layer was separated and dried over anhydrous Na2SO4, the desiccant was removed by filtration and the resulting filtrate was concentrated under vacuum to evaporate the organic solvent. The resulting residue was purified by silica gel column chromatography (PE: EA = 2:1) to afford the compound with the amino group protected by Boc. Finally, a solution of dilute hydrochloric acid in ethyl acetate was added to the crude product and the resulting reaction mixture was reacted at 0 degree C for 2-3 hours to afford the target product molecule glycine benzyl ester hydrochloride.