Transforming monosaccharides: Recent advances in rare sugar production and future exploration
Rare sugars are defined as monosaccharides and their derivatives that do not exist in nature at all or that exist in extremely limited amounts despite being theoretically possible. At present, no comprehensive dogma has been presented regarding how and why these rare sugars have deviated from the na...
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Elsevier
2025-01-01
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| author | Shin-ichi Nakakita Jun Hirabayashi |
| author_facet | Shin-ichi Nakakita Jun Hirabayashi |
| author_sort | Shin-ichi Nakakita |
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| description | Rare sugars are defined as monosaccharides and their derivatives that do not exist in nature at all or that exist in extremely limited amounts despite being theoretically possible. At present, no comprehensive dogma has been presented regarding how and why these rare sugars have deviated from the naturally selected monosaccharides. In this minireview, we adopt a hypothesis on the origin and evolution of elementary hexoses, previously presented by one of the authors (Hirabayashi, Q Rev Biol, 1996, 71:365–380). In this scenario, monosaccharides, which constitute various kinds of glycans in nature, are assumed to have been generated by formose reactions on the prebiotic Earth (chemical evolution era). Among them, the most stable hexoses, i.e., fructose, glucose, and mannose remained accumulated. After the birth of life, the “chemical origin” saccharides thus survived were transformed into a variety of “bricolage products”, which include galactose and other recognition saccharides like fucose and sialic acid through the invention of diverse metabolic pathways (biological evolution era). The remaining monosaccharides that have deviated from this scenario are considered rare sugars. If we can produce rare sugars as we wish, it is expected that various more useful biomaterials will be created by using them as raw materials. Thanks to the pioneering research of the Izumori group in the 1990′s, and to a few other investigations by other groups, almost all monosaccharides including l-sugars can now be produced by combining both chemical and enzymatic approaches. After briefly giving an overview of the origin of elementary hexoses and the current state of the rare sugar production, we will look ahead to the next generation of monosaccharide research which also targets glycosides including disaccharides. |
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| institution | Kabale University |
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| spelling | doaj-art-6c4f368d8f1847ac95bed71e2d63aa5e2025-01-26T05:05:17ZengElsevierBBA Advances2667-16032025-01-017100143Transforming monosaccharides: Recent advances in rare sugar production and future explorationShin-ichi Nakakita0Jun Hirabayashi1Department of Basic Life Science, Faculty of Medicine, Kagawa University, 1750-1, Ikenobe, Miki-cho, Kita-gun, Kagawa 761-0793, Japan; International Institute of Rare Sugar Research and Education, Kagawa University, Saiwai, Takamatsu, Kagawa 760-8521 Japan; Corresponding author at: Department of Basic Life Science, Faculty of Medicine, Kagawa University, 1750-1, Ikenobe, Miki-cho, Kita-gun, Kagawa 761-0793, Japan.Department of Basic Life Science, Faculty of Medicine, Kagawa University, 1750-1, Ikenobe, Miki-cho, Kita-gun, Kagawa 761-0793, Japan; Institute for Glyco-core Research, Nagoya University, Furu-cho, Chikusa-ku, Nagoya 464-0814, JapanRare sugars are defined as monosaccharides and their derivatives that do not exist in nature at all or that exist in extremely limited amounts despite being theoretically possible. At present, no comprehensive dogma has been presented regarding how and why these rare sugars have deviated from the naturally selected monosaccharides. In this minireview, we adopt a hypothesis on the origin and evolution of elementary hexoses, previously presented by one of the authors (Hirabayashi, Q Rev Biol, 1996, 71:365–380). In this scenario, monosaccharides, which constitute various kinds of glycans in nature, are assumed to have been generated by formose reactions on the prebiotic Earth (chemical evolution era). Among them, the most stable hexoses, i.e., fructose, glucose, and mannose remained accumulated. After the birth of life, the “chemical origin” saccharides thus survived were transformed into a variety of “bricolage products”, which include galactose and other recognition saccharides like fucose and sialic acid through the invention of diverse metabolic pathways (biological evolution era). The remaining monosaccharides that have deviated from this scenario are considered rare sugars. If we can produce rare sugars as we wish, it is expected that various more useful biomaterials will be created by using them as raw materials. Thanks to the pioneering research of the Izumori group in the 1990′s, and to a few other investigations by other groups, almost all monosaccharides including l-sugars can now be produced by combining both chemical and enzymatic approaches. After briefly giving an overview of the origin of elementary hexoses and the current state of the rare sugar production, we will look ahead to the next generation of monosaccharide research which also targets glycosides including disaccharides.http://www.sciencedirect.com/science/article/pii/S2667160325000067AldohexoseKetohexoseRare sugarLobry de Bruyn transformationEnediol intermediateKeto-enol tautomerism |
| spellingShingle | Shin-ichi Nakakita Jun Hirabayashi Transforming monosaccharides: Recent advances in rare sugar production and future exploration BBA Advances Aldohexose Ketohexose Rare sugar Lobry de Bruyn transformation Enediol intermediate Keto-enol tautomerism |
| title | Transforming monosaccharides: Recent advances in rare sugar production and future exploration |
| title_full | Transforming monosaccharides: Recent advances in rare sugar production and future exploration |
| title_fullStr | Transforming monosaccharides: Recent advances in rare sugar production and future exploration |
| title_full_unstemmed | Transforming monosaccharides: Recent advances in rare sugar production and future exploration |
| title_short | Transforming monosaccharides: Recent advances in rare sugar production and future exploration |
| title_sort | transforming monosaccharides recent advances in rare sugar production and future exploration |
| topic | Aldohexose Ketohexose Rare sugar Lobry de Bruyn transformation Enediol intermediate Keto-enol tautomerism |
| url | http://www.sciencedirect.com/science/article/pii/S2667160325000067 |
| work_keys_str_mv | AT shinichinakakita transformingmonosaccharidesrecentadvancesinraresugarproductionandfutureexploration AT junhirabayashi transformingmonosaccharidesrecentadvancesinraresugarproductionandfutureexploration |