6857-22-3Relevant articles and documents
An Enzymatic N-Acylation Step Enables the Biocatalytic Synthesis of Unnatural Sialosides
Flitsch, Sabine L.,Guo, Juan,Huang, Kun,Huang, Ying-Ying,Laborda, Pedro,Liu, Li,Lu, Ai-Min,Lyu, Yong-Mei,Parmeggiani, Fabio,Voglmeir, Josef,Wang, Wen-Jiao
supporting information, p. 5308 - 5311 (2020/02/11)
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.
Synthesis and characterization of N-acyl-tetra-O-acyl glucosamine derivatives
Dang, Chi-Hien,Nguyen, Cong-Hao,Nguyen, Thanh-Danh,Im, Chan
, p. 6239 - 6245 (2014/01/23)
Novel 1,3,4,6-tetra-O-acyl-N-acyl-d-glucosamine derivatives were synthesized from glucosamine hydrochloride (GlcN·HCl) by the acylation with pyridine as a catalyst. A derivative of tetra-O-acetyl glucosamine contained ketoprofen, a non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic effects, was first synthesized. In analysis of the NMR spectra, the ratio of α:β-anomer showed that penta-acyl-d- glucosamine derivatives and N-acetylated glucosamines containing O-acyl groups have been only the α-anomer. Meanwhile, both the intermediates and the glucoconjugate compound of ketoprofen have only the β-anomer.
Sialic acid and N-acyl sialic acid analog production by fermentation of metabolically and genetically engineered Escherichia coli
Lundgren, Benjamin R.,Boddy, Christopher N.
, p. 1903 - 1909 (2008/02/10)
Sialic acid is the terminal sugar found on most glycoproteins and is crucial in determining serum half-life and immunogenicity of glycoproteins. Sialic acid analogs are antiviral therapeutics as well as crucial tools in bacterial pathogenesis research, immunobiology and development of cancer diagnostic imaging. The scarce supply of sialic acid hinders production of these materials. We have developed an efficient, rapid and cost effective fermentation route to access sialic acid. Our approach uses low cost feedstock, produces an industrially relevant amount of sialic acid and is scalable to manufacturing levels. We have also shown that precursor directed biosynthesis can be used to produce a N-acyl sialic acid analog. This work demonstrates the feasibility of engineering manufacturing-friendly bacteria to produce complex, unavailable small molecules. The Royal Society of Chemistry.