Synthesis of l-glucose and l-galactose derivatives from d-sugars

Xia, Tianyu; Li, Yang-Bing; Yin, Zhaojun; Meng, Xiangbao; Li, Shuchun; Li, Zhongjun

doi:10.1016/j.cclet.2014.06.007

Cited by 17 publications

(12 citation statements)

References 45 publications

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“…Subsequent decarboxylation of the C6 α-oxy carboxylic acid leads to a new hemiacetal with an inverted stereochemistry at the “new” C5. This method was first explored by Shiozaki, and later by van Boom and collaborators, for the synthesis of l -glucose from d -glucono-1,5-lactone. , Recently, the concept has been rediscovered by Li and co-workers, who synthesized l -glucose, l -mannose, and l -galactose from d -glucose. , Here, the β- C -glycoside 165 was prepared from d -glucosyl acetate 164 using Co(CO) 8 -catalyzed silyloxymethylation (Scheme ). Exchange of the triethylsilyl protection group to the more stable tert -butyldiphenylsilyl group followed by benzylidene opening gave the primary alcohol 167 .…”

Section: Synthesis Of L-aldohexoses From Carbohydratesmentioning

confidence: 99%

Synthesis of l-Hexoses

2015

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Section: Synthesis Of L-aldohexoses From Carbohydratesmentioning

confidence: 99%

Synthesis of l-Hexoses

2015

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“…Recently, l -sugars have come into focus as they are frequently found to be key constituents of biologically relevant molecules [1,2], such as bioactive oligosaccharides [3], antibiotics [4], and clinically useful nucleosides [5], the latter being known as building blocks for anticancer and antiviral drugs. A pioneering example thereof is 3TC, an l -nucleoside analogue which is highly effective against HIV and hepatitis B [6].…”

Section: Introductionmentioning

confidence: 99%

Characterization of the First Bacterial and Thermostable GDP-Mannose 3,5-Epimerase

Gevaert

Overtveldt

Beerens

et al. 2019

IJMS

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GDP-mannose 3,5-epimerase (GM35E) catalyzes the conversion of GDP-mannose towards GDP-l-galactose and GDP-l-gulose. Although this reaction represents one of the few enzymatic routes towards the production of l-sugars and derivatives, it has not yet been exploited for that purpose. One of the reasons is that so far only GM35Es from plants have been characterized, yielding biocatalysts that are relatively unstable and difficult to express heterologously. Through the mining of sequence databases, we succeeded in identifying a promising bacterial homologue. The gene from the thermophilic organism Methylacidiphilum fumariolicum was codon optimized for expression in Escherichia coli, resulting in the production of 40 mg/L of recombinant protein. The enzyme was found to act as a self-sufficient GM35E, performing three chemical reactions in the same active site. Furthermore, the biocatalyst was highly stable at temperatures up to 55 °C, making it well suited for the synthesis of new carbohydrate products with application in the pharma industry.

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“…Recently, l -sugars have attracted scientific and industrial attention due to their importance as key constituents of biologically relevant molecules ( Xia et al, 2014 ; Hélaine et al, 2015 ) [e.g., in antibiotics ( Yu et al, 2013 ), bioactive oligosaccharides ( Mulloy and Forster, 2000 )] and potential for the pharmaceutical industry as building blocks for antiviral and anticancer drugs (i.e., nucleosides analogues) ( Mathé and Gosselin, 2006 ). An example of the latter is lamivudine (also known as 3TC), an l -nucleoside analogue that is used as antiretroviral medication to prevent and treat HIV/AIDS and treat chronic hepatitis B ( Gumina et al, 2001 ).…”

Section: Introductionmentioning

confidence: 99%

GDP-Mannose 3,5-Epimerase: A View on Structure, Mechanism, and Industrial Potential

Beerens

Gevaert

Desmet

2022

Front. Mol. Biosci.

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GDP-mannose 3,5-epimerase (GM35E, GME) belongs to the short-chain dehydrogenase/reductase (SDR) protein superfamily and catalyses the conversion of GDP-d-mannose towards GDP-l-galactose. Although the overall reaction seems relatively simple (a double epimerization), the enzyme needs to orchestrate a complex set of chemical reactions, with no less than 6 catalysis steps (oxidation, 2x deprotonation, 2x protonation and reduction), to perform the double epimerization of GDP-mannose to GDP-l-galactose. The enzyme is involved in the biosynthesis of vitamin C in plants and lipopolysaccharide synthesis in bacteria. In this review, we provide a clear overview of these interesting epimerases, including the latest findings such as the recently characterized bacterial and thermostable GM35E representative and its mechanism revision but also focus on their industrial potential in rare sugar synthesis and glycorandomization.

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Synthesis of l-glucose and l-galactose derivatives from d-sugars

Cited by 17 publications

References 45 publications

Synthesis of l-Hexoses

Synthesis of l-Hexoses

Characterization of the First Bacterial and Thermostable GDP-Mannose 3,5-Epimerase

GDP-Mannose 3,5-Epimerase: A View on Structure, Mechanism, and Industrial Potential

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