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Novel and Efficient Chemoenzymatic Synthesis of D ‐Glucose 6‐Phosphate and Molecular Modeling Studies on the Selective Biocatalysis
Author(s) -
RodríguezPérez Tatiana,
Lavandera Iván,
Fernández Susana,
Sanghvi Yogesh S.,
Ferrero Miguel,
Gotor Vicente
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700017
Subject(s) - candida rugosa , chemistry , phosphonate , biocatalysis , anomer , lipase , hydrolysis , stereoselectivity , substrate (aquarium) , yield (engineering) , acetylation , selectivity , organic chemistry , catalysis , combinatorial chemistry , enzyme , biochemistry , reaction mechanism , oceanography , materials science , metallurgy , gene , geology
A concise chemoenzymatic synthesis of glucose 6‐phosphate is described. Candida rugosa lipase was found to be an efficient catalyst for both regio‐ and stereoselective deacetylation of the primary hydroxy group in the peracetylated D ‐glucose. In addition, we report an improved synthesis of 1,2,3,4,6‐penta‐ O ‐acetyl‐α‐ D ‐glucopyranose providing a large‐scale procedure for the acetylation of α‐ D ‐glucose without isomerization at the anomeric center. The high overall yield and the easy scalability makes this chemoenzymatic strategy attractive for industrial application. Furthermore, molecular modeling of phosphonate transition‐state analog for the enzymatic hydrolysis step supports the substrate selectivity observed with Candida rugosa lipase.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)