Both carbohydrate monomers L-gulose and L-galactose are rarely found in nature, but are of great importance in pharmacy R&D and manufacturing. A method for the production of L-gulose and L-galactose is described that utilizes recombinant Escherichia coli harboring a unique mannitol dehydrogenase. The recombinant E. coli system was optimized by genetic manipulation and directed evolution of the recombinant protein to improve conversion. The resulting production process requires a single step, represents the first readily scalable system for the production of these sugars, is environmentally friendly, and utilizes inexpensive reagents, while producing L-galactose at 4.6 g L(-1)d(-1) and L-gulose at 0.90 g L(-1)d(-1).
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http://dx.doi.org/10.1016/j.carres.2009.11.023 | DOI Listing |
J Exp Bot
May 2024
Arkansas Biosciences Institute, Arkansas State University, PO Box 639, State University, AR 72467, USA.
l-Ascorbic acid (AsA) is an antioxidant with important roles in plant stress physiology, growth, and development. AsA also plays an essential role in human health, preventing scurvy. Humans do not synthesize AsA, which needs to be supplied via a diet rich in fresh produce.
View Article and Find Full Text PDFMolecules
May 2022
Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary.
l-Hexoses are important components of biologically relevant compounds and precursors of some therapeuticals. However, they typically cannot be obtained from natural sources and due to the complexity of their synthesis, their commercially available derivatives are also very expensive. Starting from one of the cheapest d-hexoses, d-mannose, using inexpensive and readily available chemicals, we developed a reaction pathway to obtain two orthogonally protected l-hexose thioglycoside derivatives, l-gulose and l-galactose, through the corresponding 5,6-unsaturated thioglycosides by C-5 epimerization.
View Article and Find Full Text PDFPlants (Basel)
June 2021
Council for Agricultural Research and Economics, Research Centre for Olive, Fruit and Citrus Crops, Corso Savoia 190, 95024 Acireale, Italy.
Sweet oranges are an important source of ascorbic acid (AsA). In this study, the content of AsA in the juice and leaves of four orange clonal selections, different in terms of maturity time and the presence/absence of anthocyanins, was correlated with the transcription levels of the main genes involved in the biosynthesis, recycling, and degradation pathways. Within each variety, differences in the above pathways and the AsA amount were found between the analysed tissues.
View Article and Find Full Text PDFInt J Biol Macromol
December 2020
Centre for Synthetic Biology, Department of Biotechnology, Ghent University, Coupure Links 653, 9000 Gent, Belgium. Electronic address:
GDP-mannose 3,5-epimerase (GM35E) catalyzes the double epimerization of GDP-mannose to yield GDP-l-galactose. GDP-l-gulose (C5-epimer) has previously been detected as a byproduct of this reaction, indicating that C3,5-epimerization occurs through an initial epimerization at C5. Given these products, GM35E constitutes a valuable bridge between d- and l-hexoses.
View Article and Find Full Text PDFInt J Mol Sci
July 2019
Centre for Synthetic Biology, Department of Biotechnology, Ghent University, Coupure links 653, 9000 Gent, Belgium.
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.
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