Activity and enantioselectivity in the hydrolysis of substituted phenyl esters catalysed by imidazole-containing poly(iminomethylenes)

✍ Scribed by J. M. van der Eijk; R. J. M. Nolte; V. E. M. Richters; W. Drenth

• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 516 KB
• Volume: 100
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19811000603

✦ Synopsis

Abstract

The hydrolysis of achiral and chiral esters by optically active poly(iminomethylenes), [R‐NC<]~n~, which contain imidazole groups in their side chains R, has been studied. The polymers include poly(L‐ and D‐carbylalanyl‐L‐histidine), 2d and 2e, poly(D‐carbylalanyl‐L‐histidinol), 2f, and poly(L‐carbyl‐α‐methylhistamine), 1c. The esterolytic catalytic activity of the polymers towards neutral and charged esters increases in the series 2d, 2e >> 1c < 2f. Poly(D‐carbylalanyl‐L–histidinol) shows enantioselectivity in the hydrolysis of p‐nitrophenyl esters of D‐ and L‐amino acids, k~L~/k~D~ = 1.1.