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Chemoenzymatic Synthesis of Glycoconjugates Mediated by Regioselective Enzymatic Hydrolysis of Acetylated 2‐Amino Pyranose Derivatives
Author(s) -
Zheng Changping,
Bavaro Teodora,
Tengattini Sara,
Mascherpa Andrea Gualla,
Sollogoub Matthieu,
Zhang Yongmin,
Terreni Marco
Publication year - 2019
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.201900382
Subject(s) - chemistry , glycoconjugate , regioselectivity , hydrolysis , pyranose , enzymatic hydrolysis , glucosamine , galactosamine , biochemistry , organic chemistry , catalysis
Highly regioselective deprotection of a series of 2‐amino pyranose building blocks was achieved by enzymatic hydrolysis. These monodeprotected intermediates were successfully used in the synthesis of a variety of glycoconjugate derivatives with a core of glucosamine or galactosamine, including neo‐glycoproteins and glycosphingolipids. The hydrolysis catalyzed by acetylxylan esterase from Bacillus pumilus (AXE) is suitable for the synthesis of neo ‐glycoproteins with an N ‐acetyl glucosamine core. The hydrolysis catalyzed by Candida rugosa lipase (CRL) was successfully applied in the preparation of new sialylated glycolipids starting from glucosamine building blocks protected as phthalimide. This chemoenzymatic approach can be used for the preparation of new glycoconjugate products with anticancer activity.