Enzymatic Synthesis of P-Nitrophenyl β-Chitobioside

作者: Jiří Kubisch , Lenka Weignerová , Sven Kötter , Thisbe K. Lindhorst , Petr Sedmera

DOI: 10.1080/07328309908544047

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摘要: ABSTRACT p-Nitrophenyl β-chitobioside (2) was prepared from p-nitrophenyl 2-acetamido-2--deoxy-β-D-glucopyranoside (1) using β-N-acetylhexosaminidase Aspergillus oryzae. As minor by-product a (1→6)-linked regioisomer (3a) formed. Addition of (NH4)2SO4 and organic co-solvents (acetonitrile, dioxane) substantially increased the yield.

参考文章(16)
Kurt G.I. Nilsson, Anna Eliasson, Hefeng Pan, Mattias Rohman, Synthesis of disaccharide derivatives employing β-N-acetyl- d-hexosaminidase, β-d-galactosidase and β-d-glucuronidase Biotechnology Letters. ,vol. 21, pp. 11- 15 ,(1999) , 10.1023/A:1005439302682
K. Bezouska, G. Vlahas, O. Horváth, G. Jinochová, A. Fiserová, R. Giorda, W.H. Chambers, T. Feizi, M. Pospísil, Rat natural killer cell antigen, NKR-P1, related to C-type animal lectins is a carbohydrate-binding protein. Journal of Biological Chemistry. ,vol. 269, pp. 16945- 16952 ,(1994) , 10.1016/S0021-9258(19)89481-4
Vladimír Křen, Eva Rajnochová, Zdenka Huňková, Jana Dvořáková, Petr Sedmera, Unusual nonreducing sugar GlcNAcβ(1↔1)Manβ formation by β-N-acetylhexosaminidase from Aspergillus oryzae Tetrahedron Letters. ,vol. 39, pp. 9777- 9780 ,(1998) , 10.1016/S0040-4039(98)02171-6
S.E. Zurabyan, T.P. Volosyuk, A.J. Khorlin, Oxazoline synthesis of 1,2-trans-2-acetamido-2-deoxyglycosides Carbohydrate Research. ,vol. 9, pp. 215- 220 ,(1969) , 10.1016/S0008-6215(00)82136-9
Suddham Singh, John Packwood, Christopher J Samuel, P Critchley, David HG Crout, None, Glycosidase-catalysed oligosaccharide synthesis: preparation of N-acetylchitooligosaccharides using the β-N-acetylhexosaminidase of Aspergillus oryzae Carbohydrate Research. ,vol. 279, pp. 293- 305 ,(1995) , 10.1016/0008-6215(95)00302-9
Karel Bezouška, Vladimír Křen, Christoffer Kieburg, Thisbe K Lindhorst, RETRACTED: GlcNAc-terminated glycodendrimers form defined precipitates with the soluble dimeric receptor of rat natural killer cells, sNKR-P1A FEBS Letters. ,vol. 426, pp. 243- 247 ,(1998) , 10.1016/S0014-5793(98)00340-8
W. Bremser, M. Klier, E. Meyer, Mutual assignment of subspectra and substructures—A way to structure elucidation by13C NMR spectroscopy Organic Magnetic Resonance. ,vol. 7, pp. 97- 106 ,(1975) , 10.1002/MRC.1270070211
Christoffer Kieburg, Thisbe K. Lindhorst, Glycodendrimer synthesis without using protecting groups Tetrahedron Letters. ,vol. 38, pp. 3885- 3888 ,(1997) , 10.1016/S0040-4039(97)00760-0