Glucose iso~erase EC 5.3.1.5 as a reagent in carbohydrate synthesis success and failures with the iso~e~sation of non natural derivatives of m=glucose into the corresponding 2 ketoses英文文献.pdfVIP

today CatalysisToday 22 ( 1994)549-561 Glucose iso~erase (EC 5.3.1.5) as a reagent in carbohydrate synthesis: success and failures with the iso~e~sation of non-natural derivatives of m=glucose into the corresponding 2-ketoses A. de Raadt, M. Ebner, C.W. Ekhart, M. Fechter, A. Lechner, M. Strobl, A.E. Stiitz * fnstitutfiir Organische Chemie der Technischen UniversitiitGraz, Srremayrgasxe 16.A-8010 Graz.Austria Abstract The properties of glucose isomerase {EC 5.3.1.5) and its synthetic applications are briefly reviewed and recent results with non-natural substrates are discussed. Commercially available immobilized glucose isomerase from Streptomyces murinus, previously discovered to accept D-glucose as well as D-fructose derivatives with modifications at C-3, C-5, and C-6, was also found to be an efficient catalyst for the conversion of 5,6-dim~ifi~ derivatives of D-glucose as well as 5-modified D- xylofuranose into the corresponding open-chain Z-ketoses. The equihbrium mixture in all but one case investigated favoured the respective ketose in ratios of 3: 1to 4: 1.These results are in agreement with molecular modelling experiments suggesting that the free energies of the furanoid aldoses serving as starting materials are generally slightly higher than the values for the coKesponding open-chain ketose. Dimerisation of the open-chain sugar derivatives was not observed. 1. Introduction ~rg~om~~llic as well as biocatalysts are currently thought to bear high potential for the future development of organ