Enzymatic synthesis of carnosine derivatives catalysed by Burkholderia cepacia lipase

A new enzymatic synthesis of α,β-dipeptides has been developed with particular focus on the preparation of carnosine (β-alanyl-α-histidine) and analogues. The lipase PS-D from Burkholderia cepacia has been used as a catalyst for the formation of the peptide bond starting from a β-lactam and a protected α-amino acid.

Figure optionsDownload as PowerPoint slide

N-Boc-β-alanyl-l-phenylalanine t-butyl esterC21H32N2O5[α]D24=-25.9 (c 9.70, CHCl3)Source of chirality: L-phenylalanineAbsolute configuration: (2S)

N-Boc-β-alanyl-L-histidine t-butyl esterC18H32N4O5[α]D24=-6.1 (c 10.5, CHCl3)Source of chirality: L-histidineAbsolute configuration: (2S)

N-Boc-β-alanyl-l-Trt-histidine t-butyl esterC37H46N4O5[α]D24=+9.6 (c 14.6, CHCl3)Source of chirality: L-histidineAbsolute configuration: (2S)