Efficient biosynthesis of d-allose from d-psicose by cross-linked recombinant l-rhamnose isomerase: Separation of product by ethanol crystallization

Menavuvu, Buetusiwa Thomas; Poonperm, Wayoon; Leang, Khim; Noguchi, Naoki; Okada, Hiromi; Morimoto, Kenji; Granström, Tom; Takada, Goro; Izumori, Ken

doi:10.1263/jbb.101.340

Cited by 63 publications

(33 citation statements)

References 29 publications

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“…2). A similar conversion occurred using D-psicose at 1.25, 2.5, and 5 g l À1 with 2.8 units enzyme ml À1 for 6 h. Previously, the L-RI from P. stutzeri converted 100 g D-psicose l À1 into 25 g D-allose l À1 with 8 g D-altrose l À1 as a by-product Table 1 Sugar conversion yield of ribose-5-phosphate isomerase of C. thermocellum (Menavuvu et al 2006) and an immobilized L-RI produced 150 g D-allose l À1 from 500 g D-psicose l À1 as a by-product . The yield and concentration of D-allose obtained with RpiB of C. thermocellum were therefore higher than those with L-RI of P. stutzeri which, unfortunately, produced a significant amount of D-altrose as a by-product, which is a serious problem in the purification of D-allose.…”

Section: Bioconversion Of D-psicose Into D-allosementioning

confidence: 75%

“…Moreover, a combination use of D-allose as a potent immunosuppressant with a low dose of FK506 significantly increased the rate of allograft survival with less tissue damage (Hossain et al 2000). The biological manufacture of D-allose has been studied using L-rhamnose isomerase (L-RI) from Pseudomonas stutzeri, which is the only reported enzyme (Bhuiyan et al 1998;Leang et al 2004a;Morimoto et al 2006;Menavuvu et al 2006). Therefore, the investigation and further development for other sources of enzymes to produce D-allose should be greatly needed.…”

Section: Introductionmentioning

confidence: 99%

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Characterization of ribose-5-phosphate isomerase of Clostridium thermocellum producing d-allose from d-psicose

et al. 2007

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The rpiB gene, encoding ribose-5-phosphate isomerase (RpiB) from Clostridium thermocellum, was cloned and expressed in Escherichia coli. RpiB converted D-psicose into D-allose but it did not convert D-xylose, L-rhamnose, D-altrose or D-galactose. The production of D-allose by RpiB was maximal at pH 7.5 and 65 degrees C for 30 min. The half-lives of the enzyme at 50 degrees C and 65 degrees C were 96 h and 4.7 h, respectively. Under stable conditions of pH 7.5 and 50 degrees C, 165 g D-allose l(-1 ) was produced without by-products from 500 g D-psicose l(-1) after 6 h.

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Section: Bioconversion Of D-psicose Into D-allosementioning

confidence: 75%

Section: Introductionmentioning

confidence: 99%

Characterization of ribose-5-phosphate isomerase of Clostridium thermocellum producing d-allose from d-psicose

et al. 2007

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“…11,12 These studies were aimed at finding a cost-efficient means of producing D-allose, due to its reported medical applications. 13 We do not know of any evidence that the organisms themselves utilize the enzymes in the metabolism of D-allose.…”

Section: Accepted M Manuscriptmentioning

confidence: 99%

d-Ribose-5-Phosphate Isomerase B from Escherichia coli is Also a Functional d-Allose-6-Phosphate Isomerase, While the Mycobacterium tuberculosis Enzyme is Not

Roos

Mariano

Kowalinski

et al. 2008

Journal of Molecular Biology

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SummaryInterconversion of D-ribose 5-phosphate and D-ribulose 5-phosphate is an important step in the pentose phosphate pathway. Two unrelated enzymes with D-ribose-5-phosphate isomerase activity were first identified in Escherichia coli, RpiA and RpiB. In this organism, the essential 5-carbon sugars were thought to be processed by RpiA, while the primary role of RpiB was suggested instead to be interconversion of the rare 6-carbon sugars, D-allose 6-phosphate and D-allulose 6-phosphate. In Mycobacterium tuberculosis, where only an RpiB is found, the 5-carbon sugars are believed to be the enzyme's primary substrates. Here we present kinetic studies examining the D-allose-6-phosphate isomerase activity of the RpiBs from these two organisms, and show that only the E. coli Keywords: Ribose-5-phosphate isomerase; allose-6-phosphate isomerase; rare sugar; Xray crystallography; Rv2465c. A C C E P T E D M A N U S C R I P T ACCEPTED MANUSCRIPT

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“…Meanwhile, the physiological effects of rare sugars, such as and can be industrially obtained from d-psicose by using rhamnose isomerase (Menavuvu et al, 2006). For example, d-allose has been shown to protect against inflammatory and oxidative ischemia/ reperfusion (I/R) injury in liver, retinal, and cerebral injuries in rodent models (Hossain et al, 2003;Hirooka et al, 2006;Gao et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Dietary D-Allose Ameliorates Hepatic Inflammation in Mice with Non-alcoholic Steatohepatitis

Yamamoto

Iida

Tanikawa

et al. 2017

FSTR

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Nonalcoholic steatohepatitis (NASH) is characterized by excess lipid accumulation and inflammation inhepatocytes. In this study, to provide insight into the preventive effects of d-allose, a rare sugar, on the onset of NASH, we designed animal experiments using male STAM mice treated with streptozotocin and fed a high-fat diet (HFD). Experiments were initiated when the mice reached 5 weeks of age and lasted 3 weeks. After the 3-week protocol, mice fed the HFD containing d-allose exhibited significantly decreased serum alanine aminotransferase levels, hepatic lipid accumulation and inflammation, and improved nonalcoholic fatty liver disease activity score compared to mice fed HFD without d-allose ( p < 0.05). Further, hepatic mRNA expression of sterol regulatory element binding protein-1 (Srebp-1) and monocyte chemotactic protein-1 (Mcp-1) was lower in mice fed d-allose.These results suggested that d-allose prevented NASH by blocking hepatic lipid accumulation and progressive inflammation.Keywords: nonalcoholic fatty liver disease, nonalcoholic steatohepatitis, rare sugar, d-allose IntroductionNonalcoholic fatty liver disease (NAFLD) is an increasingly common hepatic phenotype of metabolic syndrome not caused by chronic alcohol consumption and is characterized by lipid accumulation in hepatocytes (Williams et al., 2011). Nonalcoholic steatohepatitis (NASH), a type of NAFLD, is a significant risk factor for the development of cirrhosis and hepatocellular carcinoma (Feldstein et al., 2009;Cohen et al., 2011). The two-hit theory (Day and James, 1998) and multiple parallel hits hypothesis (Tilg et al., 2010) have been used to explain the progression of simple steatosis to NASH via lipid accumulation, inflammation, and oxidative stress in the liver, although the exact mechanisms R. Yamamoto et al. 320 have not yet been elucidated.In the alternative medicinal food sciences, recent reports have claimed that excessive sugar intake (e.g., d-fructose and highfructose corn syrup) is a high risk factor in the progression of NAFLD/NASH (Abdelmalek et al., 2010;Nseir et al., 2010).Meanwhile, the physiological effects of rare sugars, such as shown to protect against inflammatory and oxidative ischemia/ reperfusion (I/R) injury in liver, retinal, and cerebral injuries in rodent models (Hossain et al., 2003;Hirooka et al., 2006;Gao et al., 2013). Previous studies have revealed the physiological benefits Materials and MethodsAnimals and experimental design, and sample preparation STAM mice were used to model NASH and were obtained according to the method described by Fujii et al. (2013). Pathogenfree, 14-day pregnant female C57BL/6J mice were purchased from Charles River Laboratories (Tokyo, Japan). To induce NASH, STAM mice were primarily obtained by treating C57BL/6J mice with a single subcutaneous injection of 200 µg STZ (SigmaAldrich, St. Louis, MO, USA) 2 days after birth. At 4 weeks of age, the mice were fed a HFD (HFD32; CLEA Japan, Tokyo, Japan) ad libitum for 1 week (the experimental scheme is shown in Fig. 1). At 5 ...

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Efficient biosynthesis of d-allose from d-psicose by cross-linked recombinant l-rhamnose isomerase: Separation of product by ethanol crystallization

Cited by 63 publications

References 29 publications

Characterization of ribose-5-phosphate isomerase of Clostridium thermocellum producing d-allose from d-psicose

Characterization of ribose-5-phosphate isomerase of Clostridium thermocellum producing d-allose from d-psicose

d-Ribose-5-Phosphate Isomerase B from Escherichia coli is Also a Functional d-Allose-6-Phosphate Isomerase, While the Mycobacterium tuberculosis Enzyme is Not

Dietary D-Allose Ameliorates Hepatic Inflammation in Mice with Non-alcoholic Steatohepatitis

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