Efficient transesterification of sucrose catalysed by the metalloprotease thermolysin in dimethylsulfoxide.
Thermolysin catalyses the formation of sucrose esters from sucrose and vinyl laurate in dimethylsulfoxide, with a specific activity of 53 nmol/min/mg and 2-O-lauroyl-sucrose as the main product. Such transesterification reactions are normally observed only when the mechanism involves an acyl enzyme intermediate, as with lipases or serine proteases, and not with metalloproteases like thermolysin. A possible reason is the affinity of the active site of thermolysin for sugar moieties, as for the potent inhibitor phosphoramidon. The reaction is not catalysed by other proteins under the same conditions, and is inhibited by removal of the active site zinc.
Pedersen
Ninfa Rangel
NR
Institute of Life Sciences, Aalborg University, Sohngårdholmsvej 49, Aalborg, Denmark.
Halling
Peter J
PJ
Pedersen
Lars Haastrup
LH
Wimmer
Reinhard
R
Matthiesen
Rune
R
Veltman
Oene Robert
OR
D002268:Carboxypeptidases / Q000737:chemistry; D043422:Carboxypeptidases A; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D004126:Dimethylformamide / Q000737:chemistry; D004800:Enzymes, Immobilized / Q000737:chemistry; D004951:Esterification; D004952:Esters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009113:Muramidase / Q000737:chemistry; D012710:Serum Albumin, Bovine / Q000737:chemistry; D012995:Solubility; D013395:Sucrose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D013820:Thermolysin / Q000737:chemistry*
D004800:Enzymes, Immobilized; D004952:Esters; C018152:sucrose monolaurate; D012710:Serum Albumin, Bovine; D013395:Sucrose; D004126:Dimethylformamide; D009113:Muramidase; D002268:Carboxypeptidases; D043422:Carboxypeptidases A; D013820:Thermolysin; D004121:Dimethyl Sulfoxide