Glycosyl fluorides in enzymatic reactions.

作者: Spencer J. Williams , Stephen G. Withers

DOI: 10.1016/S0008-6215(00)00041-0

关键词:

摘要: Glycosyl fluorides have considerable importance as substrates and inhibitors in enzymatic reactions. Their good combination of stability reactivity has enabled their use glycosyl donors with a variety carbohydrate processing enzymes. Moreover, the installation fluorine elsewhere on scaffold commonly modifies properties fluoride such that resultant compounds act slow or even enzyme action. This review covers for wild-type mutant glycosidases other enzymes catalyze transfer. The substituted transfer tools investigation mechanism is discussed, including labeling active site residues. Synthetic applications which are used transglycosylation reactions synthesis oligo- polysaccharides then covered, glycosidases, so-called glycosynthases, able to formation glycosides without competing hydrolysis. Finally, short overview phosphorylases phosphoglucomutase given.

参考文章(122)
Riikka Havukainen, Anneli Törrönen, Tuomo Laitinen, Juha Rouvinen, Covalent Binding of Three Epoxyalkyl Xylosides to the Active Site of endo-1,4-Xylanase II from Trichoderma reesei†,‡ Biochemistry. ,vol. 35, pp. 9617- 9624 ,(1996) , 10.1021/BI953052N
Paul G. Gassman, Thomas T. Tidwell, Electron-deficient carbocations Accounts of Chemical Research. ,vol. 16, pp. 279- 285 ,(1983) , 10.1021/AR00092A003
Yulei Zhang, Jeyashri Bommuswamy, Michael L. Sinnott, Kinetic Isotope Effect Study of Transition States for the Hydrolyses of .alpha.- and .beta.-Glucopyranosyl Fluorides Journal of the American Chemical Society. ,vol. 116, pp. 7557- 7563 ,(1994) , 10.1021/JA00096A012
Valerie Notenboom, Camelia Birsan, Mark Nitz, David R. Rose, R. Antony J. Warren, Stephen G. Withers, Insights into transition state stabilization of the β-1,4-glycosidase Cex by covalent intermediate accumulation in active site mutants Nature Structural & Molecular Biology. ,vol. 5, pp. 812- 818 ,(1998) , 10.1038/1852
Kazuhiko Ishikawa, Ikuo Matsui, Koichi Honda, Hiroshi Nakatani, Multi-functional roles of a histidine residue in human pancreatic α -amylase Biochemical and Biophysical Research Communications. ,vol. 183, pp. 286- 291 ,(1992) , 10.1016/0006-291X(92)91641-3
Sylvain Cottaz, Hugues Driguez, First regiospecific synthesis of 6A,6C,6E-tri-O-methylyclomaltohexaose Journal of The Chemical Society, Chemical Communications. pp. 1088- 1089 ,(1989) , 10.1039/C39890001088
T. Kasumi, Y. Tsumuraya, C. F. Brewer, H. Kersters-Hilderson, M. Claeyssens, E. J. Hehre, Catalytic versatility of Bacillus pumilus .beta.-xylosidase: glycosyl transfer and hydrolysis promoted with .alpha.- and .beta.-D-xylosyl fluoride Biochemistry. ,vol. 26, pp. 3010- 3016 ,(1987) , 10.1021/BI00385A009
Y Tanaka, W Tao, J S Blanchard, E J Hehre, Transition state structures for the hydrolysis of alpha-D-glucopyranosyl fluoride by retaining and inverting reactions of glycosylases. Journal of Biological Chemistry. ,vol. 269, pp. 32306- 32312 ,(1994) , 10.1016/S0021-9258(18)31636-3