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Regioselective Deprotection of Peracetylated Disaccharides at the Primary Position Catalyzed by Immobilized Acetyl Xylan Esterase from Bacillus pumilus
Author(s) -
Bavaro Teodora,
Filice Marco,
Bonomi Paolo,
Abu alassal Qais,
Speranza Giovanna,
Guisan Jose M.,
Terreni Marco
Publication year - 2011
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.201100944
Subject(s) - chemistry , bacillus pumilus , hydrolysis , xylan , moiety , enzyme , regioselectivity , esterase , organic chemistry , lactose , catalysis , enzymatic hydrolysis , stereochemistry , bacteria , genetics , biology
In this work peracetylated lactose and related compounds have been tested as advanced intermediate substrates in enzymatic deprotections catalyzed by acetyl xylan esterase (AXE) from Bacillus pumilus . In particular, we present a simple and efficient enzymatic procedure to obtain products bearing only one free primary hydroxy group in the C6′ position of the galactoside moiety of “lacto” carbohydrates. In particular, good yields (60–70 %) have been achieved in the hydrolysis of 1‐ O ‐methyl lactosamine and hexaacetyl lactal. The products obtained are of great interest as advanced building blocks for the synthesis of very important oligosaccharides of biological relevance.