Features and applications of microbial sugar epimerases

Applied Microbiology and Biotechnology

Volumn 84, Issue 6, 2009, Pages 1053-1060

  Ito, Susumu ^a  

^a UNIVERSITY OF THE RYUKYUS   (Japan)

Author keywords

Application; Carbohydrate; Epimerase; Prebiotics; Rare sugar

Indexed keywords

3D STRUCTURE; BIOLOGICAL PROPERTIES; CATALYTIC MECHANISMS; EPIMERASE; PREBIOTICS; RARE SUGAR;

ORGANIC COMPOUNDS; SUGAR (SUCROSE);

SUGARS;

EPIMERASE; MICROBIAL ENZYME;

BIOACTIVITY; BIOCHEMISTRY; CATALYSIS; COHORT ANALYSIS; ENZYME ACTIVITY; SUGAR; THREE-DIMENSIONAL MODELING;

BIOLOGICAL ACTIVITY; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME MECHANISM; ENZYME STRUCTURE; EPIMER; HUMAN; NONHUMAN; NUCLEOTIDE SEQUENCE; SHORT SURVEY;

ANIMALS; BACTERIA; CARBOHYDRATE EPIMERASES; CARBOHYDRATES; HUMANS; INDUSTRIAL MICROBIOLOGY; PHYLOGENY;

EID: 70349656308     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-009-2179-1     Document Type: Short Survey

References (58)

1. STM Allard MF Giraud JH Naismith 2001 Epimerases: structure, function and mechanism Cell Mol Life Sci 58 1650 1665 10.1007/PL00000803 1:CAS:528:DC%2BD3MXovVyltrs%3D
2. M Amein JM Leatherwood 1969 Mechanism of cellobiose epimerase Biochem Biophys Res Commun 36 223 227 10.1016/0006-291X(69)90318-0 1:CAS:528: DyaF1MXkvVOqsbw%3D
3. SH Bhuiyan Y Itami Y Rokui T Katayama K Izumori 1998 D-Allose production from D-psicose using immobilized L-rhamnose isomerase J Biosci Bioeng 85 539 541 1:CAS:528:DyaK1cXksFSnsrY%3D
4. J Caruthers, et al. 2006 Structure of a ribulose 5-phosphate 3-pimerase from Plasmodium falciparum Proteins 62 338 342 10.1002/prot.20764 1:CAS:528:DC%2BD28XktlalsA%3D%3D (Pubitemid 43054355)
5. TR Cataldi M Angelloti SA Bufo 1999 Method development for the quantitative determination of lactulose in heat-treated milks by HPAEC with pulsed amperometric detection Anal Chem 71 4919 4925 10.1021/ac990493u 1:CAS:528:DyaK1MXmtFWktbg%3D (Pubitemid 29521824)
6. MSJ Centeno, et al. 2006 Galactomannan hydrolysis and mannose metabolism in Cellvibrio mixtus FEMS Microbiol Lett 261 123 132 10.1111/j.1574-6968.2006. 00342.x 1:CAS:528:DC%2BD28XnvFahsLk%3D (Pubitemid 43999711)
7. A Datta 1970 Regulatory role of adenosine triphosphate on hog kidney N-acetyl-D-glucosamine 2-epimerase Biochemistry 9 3663 3770 10.1021/bi00819a011
8. CJ Dong, et al. 2003 High-resolution structures of RmlC from Streptococcus suis in complex with substrate analogs locate the active site of this class of enzyme Structure 11 715 723 10.1016/S0969-2126(03)00098-4 1:CAS:528:DC%2BD3sXksVentb0%3D (Pubitemid 37281186)
9. C Dong, et al. 2007 RmlC, a C3' and C5' carbohydrate epimerase, appears to operate via an intermediate with an unusual twist boat conversion J Mol Biol 365 146 159 10.1016/j.jmb.2006.09.063 1:CAS:528:DC%2BD28Xht1KnsrvK (Pubitemid 44821205)
10. RA Field JH Naismith 2003 Structural and mechanistic basis of bacterial sugar nucleotide-modifying enzymes Biochemistry 42 7637 7647 10.1021/bi0345079 1:CAS:528:DC%2BD3sXktVKruro%3D (Pubitemid 36758928)
11. TB Granström G Takata M Tokuda K Izumori 2004 Izumoring: a novel and complete strategy for bioproduction of rare sugars J Biosci Bioeng 97 89 94
12. B Hahn-Hägerdal K Karhumaa C Fonseca I Spencer-Martins MF Gorwa-Grauslund 2007 Towards industrial pentose-fermenting yeast strains Appl Microbiol Biotechnol 74 937 958 10.1007/s00253-006-0827-2 (Pubitemid 46434767)
13. Y Ishida T Kamiya K Izumori 1997 Production of D-tagatose 3-epimerase of Pseudomonas cichorii ST-24 using recombinant Escherichia coli J Ferment Bioeng 84 348 350 10.1016/S0922-338X(97)89257-4 1:CAS:528:DyaK2sXntlyjtL0%3D (Pubitemid 28015934)
14. S Ito, et al. 2007 Cloning and sequencing of the cellobiose 2-epimerase gene from an obligatory anaerobe, Ruminococcus albus Biochem Biophys Res Commun 360 640 645 10.1016/j.bbrc.2007.06.091 1:CAS:528:DC%2BD2sXnslSqtrw%3D (Pubitemid 47048147)
15. S Ito, et al. 2008 Enzymatic properties of cellobiose 2-epimerase from Ruminococcus albus and the synthesis of rare oligosaccharides by the enzyme Appl Microbiol Biotechnol 79 433 441 10.1007/s00253-008-1449-7 1:CAS:528: DC%2BD1cXlvF2kurw%3D
16. S Ito, et al. 2009 Site-directed mutagenesis of possible catalytic residues of cellobiose 2-epimerase from Ruminococcus albus Biotechnol Lett 31 1065 1071 10.1007/s10529-009-9979-3 1:CAS:528:DC%2BD1MXnt1elsLs%3D
17. T Itoh, et al. 2000 Crystal structure of N-acyl-D-glucosamine 2-epimerase from porcine kidney at 2.0 Å resolution J Mol Biol 303 733 744 10.1006/jmbi.2000.4188 1:CAS:528:DC%2BD3cXnslCqtrw%3D (Pubitemid 30848222)
18. TW Jeffries YS Jin 2004 Metabolic engineering for improved fermentation of pentoses by yeasts Appl Microbiol Biotechnol 63 495 509 10.1007/s00253-003- 1450-0 1:CAS:528:DC%2BD2cXmvVGjtA%3D%3D (Pubitemid 38232698)
19. HJ Kim EK Hyun YS Kim OhDK LeeYJ 2006 Characterization of an Agrobacterium tumefaciens D-psicose 3-epimerase that converts D-fructose to D-psicose Appl Environ Microbiol 72 981 985 10.1128/AEM.72.2.981-985.2006 1:CAS:528:DC%2BD28Xhs1Ghs78%3D (Pubitemid 43271199)
20. K Kim HJ Kim DK Oh SS Cha S Rhee 2006 Crystal structure of D-psicose 3-epimerase from Agrobacterium tumefaciens and its complex with true substrate D-fructose: a pivotal role of metal in catalysis, an active site for the non-phosphorylated substrate, and its conformational changes J Mol Biol 361 920 931 10.1016/j.jmb.2006.06.069 1:CAS:528:DC%2BD28XotV2kt7s%3D (Pubitemid 44189438)
21. M Kuyper, et al. 2005 Evolutionary engineering of mixed-sugar utilization by a xylose-fermenting Saccharomyces cerevisiae strain FEMS Yeast Res 5 925 934 10.1016/j.femsyr.2005.04.004 1:CAS:528:DC%2BD2MXlvFKlu74%3D (Pubitemid 40941017)
22. 6 barrel structure of Anabaena sp. CH1 N-acetyl-D-glucosamine 2-epimerase contains two key histidine residues for reversible conversion J Mol Biol 367 895 908 10.1016/j.jmb.2006.11.001 1:CAS:528:DC%2BD2sXitl2lsLc%3D (Pubitemid 46330367)
23. GV Levin 2002 Tagatose, the new GRAS sweetener and health product J Med Food 5 23 36 10.1089/109662002753723197 1:CAS:528:DC%2BD38XktlSjt7o%3D
24. Y Lu GV Levin TW Donner 2008 Tagarose, a new antidiabetic and obesity control drug Diabetes Obes Metab 10 109 134 10.1111/j.1463-1326.2008.00866.x 1:CAS:528:DC%2BD1cXivVOrtrg%3D
25. SJ Luchansky KJ Yarema S Takahashi CR Bertozzi 2003 GlcNAc 2-epimerase can serve a catabolic role in sialic acid metabolism J Biol Chem 278 8035 8042 10.1074/jbc.M212127200 1:CAS:528:DC%2BD3sXhsF2iuro%3D (Pubitemid 36800542)
26. L Luska M Krause K Danker W Reutter R Horstkorte 1999 Primary structure and expression analysis of human UDP-N-acety-glucosamine-2-epimerase/N- acetylmannosamine kinase, the bifunctional enzyme in neuraminic acid biosynthesis FEBS Lett 454 341 344 10.1016/S0014-5793(99)00837-6 (Pubitemid 29304628)
27. I Martinez-Castro A Olano N Corzo 1986 Modifications and interactions of lactose with mineral components of milk during heating processes Food Chem 21 211 221 10.1016/0308-8146(86)90019-1 1:CAS:528:DyaL2sXjvFWm (Pubitemid 16015850)
28. T Matsuo Y Shirai K Izumori 2001 Effects of dietary D-psicose on diurnal variation in plasma glucose and insulin concentrations of rats Asia Pacific J Clin Nutr 10 233 237 10.1046/j.1440-6047.2001.00246.x 1:CAS:528: DC%2BD3MXoslWhtbk%3D (Pubitemid 33322859)
29. A Melo L Glaser 1968 The mechanism of 6-deoxyhexose synthesis. II. Conversion of deoxythymidine diphosphate 4-keto-6-deoxy-D-glucose to deoxythymidine diphosphate L-rhamnose. J Biol Chem 243 1475 1478 1:STN:280:DyaF1c3jtFShtg%3D%3D
30. BT Menavuvu, et al. 2006 Efficient biosynthesis of D-allose from D-psicose by cross-linked recombinant L-rhamnose isomerase: separation of product by ethanol crystallization J Biosci Bioeng 101 340 345 10.1263/jbb.101.340 1:CAS:528:DC%2BD28XmtVahtrg%3D (Pubitemid 44354411)
31. M Miyamoto K Ajisaka 2004 Regioselectivity in β-galactosidase- catalyzed transglycosylation for the enzymatic assembly of D-galactosyl-D- mannose Biosci Biotechnol Biochem 68 2086 2090 10.1271/bbb.68.2086 (Pubitemid 39547597)
32. FJ Moreno M Villamiel A Olano 2003 Effect of high pressure on isomerization and degradation of lactose in alkaline media J Agric Food Chem 51 894 1896
33. K Murao, et al. 2007 D-Psicose inhibits the expression of MCP-1 induced by high-glucose stimulation in HUVECs Life Sci 81 592 599 10.1016/j.lfs.2007.06. 019 1:CAS:528:DC%2BD2sXovFeiu7Y%3D (Pubitemid 47212242)
34. A Murata, et al. 2003 A novel inhibitory effect of D-allose on production of reactive oxygen species from neutrophils J Biosci Bioeng 96 89 91 1:CAS:528:DC%2BD3sXnsFykt78%3D
35. T Nakakuki 2005 Present status and future prospects of functional oligosaccharide development in Japan J Appl Glycosci 52 267 271 1:CAS:528:DC%2BD2MXpvFSjtbc%3D
36. M Nishimukai, et al. 2008 Effects of epilactose on calcium adsorption and serum lipid metabolism in rats J Agric Food Chem 56 10340 10345 10.1021/jf801556m 1:CAS:528:DC%2BD1cXht1SmtrjK
37. DK Oh 2007 Tagatose: properties, applications, and biotechnological processes Appl Microbiol Biotechnol 76 1 8 10.1007/s00253-007-0981-1 1:CAS:528:DC%2BD2sXosVSksrk%3D (Pubitemid 47194675)
38. H Oshima I Kimura K Izumori 2006 Psicose contents in various food products and its origin Food Sci Technol Res 12 137 143 10.3136/fstr.12.137 1:CAS:528:DC%2BD28Xht1Gkur7L (Pubitemid 44617076)
39. B Pacheco M Maccarana DR Goodlett A Malmström L Malmström 2009 Identification of the active site of DS-epimerase 1 and requirement of N-glycosylation for enzyme function J Biol Chem 284 1741 1747 10.1074/jbc.M805479200 1:CAS:528:DC%2BD1MXjtFOhtw%3D%3D
40. J Samuel ME Tanner 2002 Mechanistic aspects of enzymatic carbohydrate epimerization Nat Prod Rep 19 261 277 10.1039/b100492l 1:CAS:528: DC%2BD38XlsFSnsbs%3D (Pubitemid 34653052)
41. M Sato H Kurose T Yamasaki K Izumori 2008 Potential anthemintic: D-psicose inhibits motility, growth and productive maturity of L1 larvae of Caenorhabditis elegans J Nat Med 62 244 246 10.1007/s11418-007-0220-1 1:CAS:528:DC%2BD1cXltVKjtrg%3D
42. Schauer R (1982) Sialic acids-chemistry, metabolism, and function. Springer, New York, pp 263-305
43. C Schmitz, et al. 2000 Normal blood pressure and plasma rennin activity in mice lacking the rennin-binding protein, a cellular rennin inhibitor J Biol Chem 275 15357 15362 10.1074/jbc.275.20.15357 1:CAS:528:DC%2BD3cXjsFams7o%3D (Pubitemid 30337264)
44. M Sedlak NWY Ho 2004 Production of ethanol from cellulosic biomass hydrolysates using genetically engineered Saccharomyces yeast capable of cofermenting glucose and xylose Appl Biochem Biotechnol 113-116 404 416
45. T Senoura, et al. 2009 Identification of the cellobiose 2-epimerase gene in the genome of Bacteroides fragilis NCTC 9343 Biosci Biotechnol Biochem 73 400 406 10.1271/bbb.80691 1:CAS:528:DC%2BD1MXivFeltbY%3D
46. R Shi, et al. 2008 Structure of L-xylulose 3-epimerase (UlaE) from the anaerobic L-ascorbate utilization pathway of Escherichia coli: identification of a novel phosphate binding motif within a TIM barrel fold J Bacteriol 190 8137 8144 10.1128/JB.01049-08 1:CAS:528:DC%2BD1cXhsV2lsLjE
47. L Sui, et al. 2005 The inhibitory effect and possible mechanisms of D-allose on cancer cell proliferation Int J Oncol 27 907 912 1:CAS:528:DC%2BD2MXhtFeisrzK
48. Y Sun S Hayakawa M Ogawa K Fukada K Izumori 2008 Influence of a rare sugar, D-psicose, on the physicochemical and functional properties of an aerated food system containing egg albumin J Agric Food Chem 56 4789 4796 10.1021/jf800050d 1:CAS:528:DC%2BD1cXms1agsbc%3D (Pubitemid 351999412)
49. H Taguchi, et al. 2008 Cloning and sequencing of the gene for cellobiose 2-epimerase from a ruminal strain of Eubacterium cellulosolvens FEMS Microbiol Lett 287 34 40 10.1111/j.1574-6968.2008.01281.x 1:CAS:528:DC%2BD1cXhtFOitrfP
50. TR Tyler JM Leatherwood 1967 Epimerization of disaccharides by enzyme preparations from Ruminococcus albus Arch Biochem Biophys 119 363 367 10.1016/0003-9861(67)90466-3 1:CAS:528:DyaF2sXotlaluw%3D%3D
51. J Watanabe, et al. 2008 Prebiotic properties of epilactose J Dairy Sci 91 4518 4526 10.3168/jds.2008-1367 1:CAS:528:DC%2BD1cXhsVKgtr3E (Pubitemid 352847741)
52. HW Wisselink, et al. 2007 Engineering of Saccharomyces cerevisiae for efficient anaerobic alcoholic fermentation of L-arabinose Appl Environ Microbiol 73 4881 4891 10.1128/AEM.00177-07 1:CAS:528:DC%2BD2sXptVyhtb8%3D (Pubitemid 47237237)
53. HW Wisselink, et al. 2009 Novel evolutionary engineering approach for accelerated utilization of glucose, xylose, and arabinose mixtures by engineered Saccharomyces cerevisiae strains Appl Environ Microbiol 75 907 914 10.1128/AEM.02268-08 1:CAS:528:DC%2BD1MXitlCrurc%3D
54. S Yamaguchi J Ohnishi I Maru Y Ohta 2006 Simple and large-scale production of N-acetylneuraminic acid and N-acetyl-D-mannosamine Trends Glycosci Glycotechnol 18 245 252 1:CAS:528:DC%2BD28XhtVyqt7bI
55. kip1 Int J Oncol 32 377 385 1:CAS:528:DC%2BD1cXitFWht7s%3D
56. H Yoshida, et al. 2007 Crystal structures of D-tagatose 3-epimerase from Pseudomonas cichorii and its complexes with D-tagatose and D-fructose J Mol Biol 374 443 453 10.1016/j.jmb.2007.09.033 1:CAS:528:DC%2BD2sXht1KjtrjK (Pubitemid 350007649)
57. L Zhang W Mu B Jiang T Zhang 2009 Characterization of D-tagatose-3-epimerase from Rhodobacter sphaeroides that converts D-fructose into D-psicose Biotechnol Lett 10.1007/s10529-009-9942-3
58. C Ziemer G Gibson 1998 An overview of probiotics, prebiotics and synbiotics in the functional food concept: perspectives and future strategies Int Dairy J 8 473 479 10.1016/S0958-6946(98)00071-5 1:CAS:528:DyaK1cXnsFGnsr0%3D (Pubitemid 28504147)