Purification and Characterization of<scp>D</scp>-Tagatose 3-Epimerase from<i>Pseudomonas</i>sp. ST-24

Itoh, Hiromichi; Okaya, Hiroaki; Khan, Anisur Rahman; Tajima, Shigeyuki; Hayakawa, Shigeru; Izumori, Ken

doi:10.1271/bbb.58.2168

Cited by 149 publications

(151 citation statements)

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“…Chemical methods for the synthesis of these rare ketoses require tedious protection/deprotection manipulations. [10] Alternatively, enzymatic preparation by epimerizing ketoses at the C-3 position, [11] oxidizing polyols, [12] or relying on aldol condensation [13] proceeds regio-and stereoselectively without protection. However, these processes suffer from low yields, expensive starting materials or a complicated isomer separation step.…”

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confidence: 99%

“…HK can also phosphorylate L-psicose efficiently while no activity towards its corresponding (3R)-ketose (L-fructose) was detected, making it possible to establish Scheme 3 for the preparation of Lpsicose from L-fructose. Another requirement for the establishment of Schemes 1 (route B) and 3 is that DTE, which catalyzes the interconversion of (3S)-and (3R)-ketoses, [11] does not epimerize ketose 1-phosphates, otherwise the products obtained finally will be a mixture containing both (3S)-ketoses and (3R)-ketoses. DTE does not recognize D-fructose 6-phosphate and D-ribulose 5-phosphate.…”

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confidence: 99%

“…DTE does not recognize D-fructose 6-phosphate and D-ribulose 5-phosphate. [11] We therefore hypothesized that it would not recognize other ketose phosphates, such as ketose 1-phosphates. This hypothesis was supported by the purity analysis of final products (Table 1).…”

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confidence: 99%

“…Having overcome these problems, other conversion-related enzymes including D-xylose isomerase (XylA), [22] RhaD [23] and AphA [18] from Escherichia coli, L-arabinose and Dgalactose isomerase (AraA) from Thermotoga maritima MSB8, [24] DTE from Pseudomonas Sp, St-24 [11] were prepared as described in supporting information.…”

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confidence: 99%

“…The discovery of DTE made it possible to achieve the interconversion between (3S)-ketoses and (3R)-ketoses and is especially important for the preparation of (3R)-ketoses. [11] Nevertheless,with the exceptions of two (3S)-ketoses (Dfructose and Lsorbose), ketoses are not readily available, and the conversions catalyzed by DTE are an equilibrium reaction. For example, the conversion ratio is only 20% for Dfructose to D-psicose and 27% for L-sorbose to L-tagatose.…”

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confidence: 99%

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Facile Enzymatic Synthesis of Ketoses

et al. 2015

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Studies of rare ketoses have been hampered by a lack of efficient preparation methods. A convenient, efficient, and cost‐effective platform for the facile synthesis of ketoses is described. This method enables the preparation of difficult‐to‐access ketopentoses and ketohexoses from common and inexpensive starting materials with high yield and purity and without the need for a tedious isomer separation step.

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confidence: 99%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Facile Enzymatic Synthesis of Ketoses

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Crystal structure of a novel homodimeric l‐ribulose 3‐epimerase from Methylomonus sp.

et al. 2021

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D-Allulose has potential as a low-calorie sweetener which can suppress fat accumulation. Several enzymes capable of D-allulose production have been isolated, including D-tagatose 3-epimerases. Here, we report the isolation of a novel protein from Methylomonas sp. expected to be a putative enzyme based on sequence similarity to ketose 3-epimerase. The synthesized gene encoding the deduced ketose 3-epimerase was expressed as a recombinant enzyme in Escherichia coli, and it exhibited the highest enzymatic activity toward L-ribulose, followed by D-ribulose and D-allulose. The X-ray structure analysis of L-ribulose 3-epimerase from Methylomonas sp. (MetLRE) revealed a homodimeric enzyme, the first reported structure of dimeric Lribulose 3-epimerase. The monomeric structure of MetLRE is similar to that of homotetrameric L-ribulose 3-epimerases, but the short C-terminal a-helix of MetLRE is unique and different from those of known L-ribulose 3 epimerases. The length of the C-terminal a-helix was thought to be involved in tetramerization and increasing stability; however, the addition of residues to MetLRE at the C terminus did not lead to tetramer formation. MetLRE is the first dimeric L-ribulose 3-epimerase identified to exhibit high relative activity toward D-allulose. D-Allulose (alternative name D-psicose) is a rare sugar, and its physiological functions, such as altering the blood glucose level, suppressing fat accumulation, and use as a low-calorie sweetener [1-9], have been focused on as a promising functional food ingredient. In Japan, a low-calorie syrup containing D-allulose, Rare Sugar Sweet Ò (Matsutani Chemical Industry Co., Ltd., Hyogo, Japan) [10], is commercially available and its labeling as a functional food was recently approved. In addition, the U.S. Food and Drug Administration (FDA) stated that 'it allows the low-calorie sweetener allulose to be excluded from total and added sugar counts on Nutrition and Supplement Facts labels when used as an ingredient' (FDA In Brief, April, 2019). AbbreviationsAgDAE, D-allulose 3-epimerase from Arthrobacter globiformis; AtDAE, D-allulose 3-epimerase from Agrobacterium tumefaciens; CcDAE, D-allulose 3-epimerase from Clostridium cellulolyticum; DAE, D-allulose 3-epimerase; his_MetLRE long2, his_MetLRE with nine additional residues (TAIKTIELH) at the C terminus and with three mutations (Y9I, Y37F, Y286L); his_MetLRE, N-terminal his-tagged MetLRE; his_MetLRE3, his_MetLRE with three mutations (Y9I, Y37F, and Y286L); LRE, L-ribulose 3-epimerase; MetLRE, L-ribulose 3-epimerase from Methylomonas sp.; MlLRE, L-ribulose 3-epimerase from Mesorhizobium loti; PcDTE, D-tagatose 3-epimerases from Pseudomonas cichorii.

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