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An Enzymatic N-Acylation Step Enables the Biocatalytic Synthesis of Unnatural Sialosides
Authors:Prof Pedro Laborda  Yong-Mei Lyu  Dr Fabio Parmeggiani  Dr Ai-Min Lu  Wen-Jiao Wang  Ying-Ying Huang  Dr Kun Huang  Juan Guo  Prof Li Liu  Prof Sabine L Flitsch  Prof Josef Voglmeir
Institution:1. Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, 1 Weigang, 210095 Nanjing, China;2. Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, 1 Weigang, 210095 Nanjing, China

These authors contributed equally to this work.;3. School of Chemistry & Manchester Institute of Biotechnology, The University of Manchester, 131 Princess Street, M1 7DN Manchester, UK;4. College of Sciences, Nanjing Agricultural University, 1 Weigang, 210095 Nanjing, China

Abstract:Chitin is one of the most abundant and cheaply available biopolymers in Nature. Chitin has become a valuable starting material for many biotechnological products through manipulation of its N-acetyl functionality, which can be cleaved under mild conditions using the enzyme family of de-N-acetylases. However, the chemoselective enzymatic re-acylation of glucosamine derivatives, which can introduce new stable functionalities into chitin derivatives, is much less explored. Herein we describe an acylase (CmCDA from Cyclobacterium marinum) that catalyzes the N-acylation of glycosamine with a range of carboxylic acids under physiological reaction conditions. This biocatalyst closes an important gap in allowing the conversion of chitin into complex glycosides, such as C5-modified sialosides, through the use of highly selective enzyme cascades.
Keywords:Acylierungen  Chitin-De-N-acetylasen  Enzymatische Synthese  Glycosylierungen  Unnatürliche Sialoside
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