Summary: Monosaccharide sugar molecules that contain a five carbon backbone.

Top Publications

  1. Eriksen N, Riis M, Holm N, Iversen N. H(2) synthesis from pentoses and biomass in Thermotoga spp. Biotechnol Lett. 2011;33:293-300 pubmed publisher
    ..neapolitana. Both species metabolised all sugars with hydrogen yields of 2.7-3.8 mol mol(-1) sugar. Both pentoses were at least comparable to glucose with respect to their qualities as substrates for hydrogen production, while ..
  2. Yoon R, Yeom S, Kim H, Oh D. Novel substrates of a ribose-5-phosphate isomerase from Clostridium thermocellum. J Biotechnol. 2009;139:26-32 pubmed publisher
    ..Ribose 5-phosphate isomerase catalyzed the conversion of L-talose to L-tagatose with an 89% conversion yield after approximately 90 min, while D-ribulose was converted to D-ribose with a 38% conversion yield. ..
  3. Roe J, Rice E. A photometric method for the determination of free pentoses in animal tissues. J Biol Chem. 1948;173:507-12 pubmed
  4. Trinh C, Unrean P, Srienc F. Minimal Escherichia coli cell for the most efficient production of ethanol from hexoses and pentoses. Appl Environ Microbiol. 2008;74:3634-43 pubmed publisher
    ..identified by elementary mode analysis, consist of four pathways with non-growth-associated conversion of pentoses and hexoses into ethanol at theoretical yields and two pathways with tight coupling of anaerobic cell growth with ..
  5. Rodas A, Chenoll E, Macián M, Ferrer S, Pardo I, Aznar R. Lactobacillus vini sp. nov., a wine lactic acid bacterium homofermentative for pentoses. Int J Syst Evol Microbiol. 2006;56:513-7 pubmed
    ..Strains ferment pentoses exclusively yielding lactic acid as the end product...
  6. Kim S, Lee S. Identification and characterization of Sulfolobus solfataricus D-gluconate dehydratase: a key enzyme in the non-phosphorylated Entner-Doudoroff pathway. Biochem J. 2005;387:271-80 pubmed publisher
    ..This is the first report on biochemical and genetic characterization of D-gluconate dehydratase involved in the non-phosphorylated Entner-Doudoroff pathway...
  7. Rashid N, Imanaka H, Fukui T, Atomi H, Imanaka T. Presence of a novel phosphopentomutase and a 2-deoxyribose 5-phosphate aldolase reveals a metabolic link between pentoses and central carbon metabolism in the hyperthermophilic archaeon Thermococcus kodakaraensis. J Bacteriol. 2004;186:4185-91 pubmed publisher
    ..Our results clearly indicate the presence of a metabolic link between pentoses and central carbon metabolism in T...
  8. Matte A, Forsberg C, Verrinder Gibbins A. Enzymes associated with metabolism of xylose and other pentoses by Prevotella (Bacteroides) ruminicola strains, Selenomonas ruminantium D, and Fibrobacter succinogenes S85. Can J Microbiol. 1992;38:370-6 pubmed
    ..ruminicola and S. ruminantium possess the essential enzymes of the nonoxidative branch of the pentose phosphate cycle. ..
  9. Leandro M, Fonseca C, Gonçalves P. Hexose and pentose transport in ascomycetous yeasts: an overview. FEMS Yeast Res. 2009;9:511-25 pubmed publisher
    ..summarize our current knowledge on the biochemical and molecular features of the transporters of hexoses and pentoses in yeasts, when possible establishing links between previous kinetic studies and genomic data currently available...

More Information


  1. Yeom S, Ji J, Kim N, Park C, Oh D. Substrate specificity of a mannose-6-phosphate isomerase from Bacillus subtilis and its application in the production of L-ribose. Appl Environ Microbiol. 2009;75:4705-10 pubmed publisher
    ..The enzyme exhibited the highest activity for l-ribulose among all pentoses and hexoses...
  2. Oreb M, Dietz H, Farwick A, Boles E. Novel strategies to improve co-fermentation of pentoses with D-glucose by recombinant yeast strains in lignocellulosic hydrolysates. Bioengineered. 2012;3:347-51 pubmed publisher
    ..Baker's yeast is an excellent, traditionally used ethanol producer but is naturally not able to utilize pentoses. This is due to the lack of pentose-specific transporter proteins and enzymatic reactions...
  3. Jeffries T, Jin Y. Metabolic engineering for improved fermentation of pentoses by yeasts. Appl Microbiol Biotechnol. 2004;63:495-509 pubmed
    ..cerevisiae and adapted strains of Pichia stipitis have been shown to ferment hydrolysates with ethanol yields of 0.45 g g(-1) sugar consumed, so commercialization seems feasible for some applications. ..
  4. Hahn Hagerdal B, Wahlbom C, Gárdonyi M, Van Zyl W, Cordero Otero R, Jönsson L. Metabolic engineering of Saccharomyces cerevisiae for xylose utilization. Adv Biochem Eng Biotechnol. 2001;73:53-84 pubmed
    ..cerevisiae. ..
  5. Scherman M, Kalbe Bournonville L, Bush D, Xin Y, Deng L, McNeil M. Polyprenylphosphate-pentoses in mycobacteria are synthesized from 5-phosphoribose pyrophosphate. J Biol Chem. 1996;271:29652-8 pubmed
    ..phosphoribose pyrophosphate was shown to be a key intermediate on the pathway to both polyprenylphosphate-D-pentoses. Thus, incubation of 5-phospho-D-[14C]ribose pyrophosphate with membranes prepared from Mycobacterium smegmatis ..
  6. Biemel K, Reihl O, Conrad J, Lederer M. Formation pathways for lysine-arginine cross-links derived from hexoses and pentoses by Maillard processes: unraveling the structure of a pentosidine precursor. J Biol Chem. 2001;276:23405-12 pubmed
    ..From these results it seems fully justified to expect both glucosepane 9 and DOGDIC 12 to constitute important in vivo cross-links. ..
  7. Bessières B, Morin C. Iodomethyl group as a hydroxymethyl synthetic equivalent: application to the syntheses of D-manno-hept-2-ulose and l-fructose derivatives. J Org Chem. 2003;68:4100-3 pubmed
  8. Adachi O, Hours R, Shinagawa E, Akakabe Y, Yakushi T, Matsushita K. Formation of 4-keto-D-aldopentoses and 4-pentulosonates (4-keto-D-pentonates) with unidentified membrane-bound enzymes from acetic acid bacteria. Biosci Biotechnol Biochem. 2011;75:1801-6 pubmed
    ..The formation of 4-keto-D-aldopentoses and 4-keto-D-pentonates (4-pentulosonates) was finally confirmed as reaction products of four different novel membrane-bound enzymes. ..
  9. Dogaris I, Gkounta O, Mamma D, Kekos D. Bioconversion of dilute-acid pretreated sorghum bagasse to ethanol by Neurospora crassa. Appl Microbiol Biotechnol. 2012;95:541-50 pubmed publisher
    ..and 8 % at fermentation), low cellulase activities (1-7 FPU/g SB) and co-fermentation of hexoses and pentoses. The fungus Neurospora crassa DSM 1129 was used, which exhibits both depolymerase and co-fermentative ability, as ..
  10. Major H, Castro Perez J, Nicholson J, Wilson I. Characterisation of putative pentose-containing conjugates as minor metabolites of 4-bromoaniline present in the urine of rats following intraperitoneal administration. Rapid Commun Mass Spectrom. 2003;17:76-80 pubmed
  11. Kumazawa T, Saito T, Matsuba S, Sato S, Onodera J. Synthesis of C-pentopyranosylphloroacetophenone derivatives and their anomerization. Carbohydr Res. 2000;329:855-9 pubmed
    ..The composition of this product mixture is apparently dictated by both 1,3-diaxial and 2,4-diaxial interactions. ..
  12. Reichvilser M, Heinzl C, Klüfers P. Boronic acid mono- and diesters of the aldopentoses. Carbohydr Res. 2010;345:498-502 pubmed publisher
    ..Lyxose and ribose formed monoesters under the conditions employed. NMR shielding constants were calculated by DFT methods. The results are highly correlated with the experimentally observed NMR shift values. ..
  13. Flanigan I, Collins J, Arora K, MacLeod J, Williams J. Exchange reactions catalyzed by group-transferring enzymes oppose the quantitation and the unravelling of the identify of the pentose pathway. Eur J Biochem. 1993;213:477-85 pubmed
    ..1-6.4 rather than the mandatory value of 2 which is imposed by the theoretical mechanism of the pathway. ..
  14. Falb M, Muller K, Königsmaier L, Oberwinkler T, Horn P, von Gronau S, et al. Metabolism of halophilic archaea. Extremophiles. 2008;12:177-96 pubmed publisher
    ..The carefully assessed metabolic data represent a reliable resource for future system biology approaches as it also links to current experimental data on (halo)archaea from the literature. ..
  15. Green M, Cohen S. Enzymatic conversion of L-fucose to L-fuculose. J Biol Chem. 1956;219:557-68 pubmed
  16. Cronin N, O Reilly A, Duclohier H, Wallace B. Effects of deglycosylation of sodium channels on their structure and function. Biochemistry. 2005;44:441-9 pubmed
    ..In summary, while the sugars of the voltage-gated sodium channels from electroplax are not essential for functional or structural integrity, they do appear to have a modulating effect on the conductance properties of these channels...
  17. Hayer K, Stratford M, Archer D. Structural features of sugars that trigger or support conidial germination in the filamentous fungus Aspergillus niger. Appl Environ Microbiol. 2013;79:6924-31 pubmed publisher
    ..We also present data on the uptake of sugars during the germination process and discuss possible mechanisms of triggering in the absence of apparent sugar uptake during the initial swelling of conidia. ..
  18. Davidek T, Kraehenbuehl K, Devaud S, Robert F, Blank I. Analysis of Amadori compounds by high-performance cation exchange chromatography coupled to tandem mass spectrometry. Anal Chem. 2005;77:140-7 pubmed
    ..Analysis of pentose-derived Amadori compounds is shown for the first time, which represents a major breakthrough in studying occurrence, formation, and decomposition of these labile Maillard intermediates. ..
  19. Zhang Y, Jeya M, Lee J. L-Ribulose production by an Escherichia coli harboring L-arabinose isomerase from Bacillus licheniformis. Appl Microbiol Biotechnol. 2010;87:1993-9 pubmed publisher
    ..coli cells were recycled, 85% of the yield was obtained even after seven cycles of reuse. The productivity and final concentration of L: -ribulose obtained in the present study were the highest yet reported. ..
  20. Avci A, Saha B, Dien B, Kennedy G, Cotta M. Response surface optimization of corn stover pretreatment using dilute phosphoric acid for enzymatic hydrolysis and ethanol production. Bioresour Technol. 2013;130:603-12 pubmed publisher
    ..0g sugars generated from enzymatically hydrolyzed corn stover (10%, w/w) pretreated under a balanced optimized condition (161.81°C, 0.78% acid, 9.78min) where only 0.4±0.0g furfural and 0.1±0.0 hydroxylmethyl furfural were produced...
  21. Yen Y, Kulkarni S, Chang C, Luo S. Concise synthesis of ?-galactosyl ceramide from D-galactosyl iodide and D-lyxose. Carbohydr Res. 2013;368:35-9 pubmed publisher
  22. Richard P, Toivari M, Penttila M. The role of xylulokinase in Saccharomyces cerevisiae xylulose catabolism. FEMS Microbiol Lett. 2000;190:39-43 pubmed
    ..We have partially purified the xylulokinase and characterised its kinetic properties. It is reversible and will also accept D-ribulose as a substrate. ..
  23. Enholm E, Cottone J, Allais F. Highly diastereoselective 5-hexenyl radical cyclizations with Lewis acids and carbohydrate scaffolds. Org Lett. 2001;3:145-7 pubmed
    ..Temperature dependence, Lewis acids, and solvents were all examined. By correlation with known compounds, the newly generated chiral centers were of the (S)-configuration. ..
  24. Banerjee S, Anderson F, Farber G. The evolution of sugar isomerases. Protein Eng. 1995;8:1189-95 pubmed
    ..This work also suggests that unless convergent evolution has been demonstrated, the mechanism of one enzyme may not give any insight into the mechanism of a second enzyme catalyzing the same reaction. ..
  25. Cieśla J. Metabolic enzymes that bind RNA: yet another level of cellular regulatory network?. Acta Biochim Pol. 2006;53:11-32 pubmed
    ..All these enzymes are ancient, as judged by their wide distribution, and participate in fundamental biochemical pathways. ..
  26. Abla M, Marmuse L, Delolme F, Vors J, Ladavière C, Trombotto S. Access to tetra-N-acetyl-chitopentaose by chemical N-acetylation of glucosamine pentamer. Carbohydr Polym. 2013;98:770-7 pubmed publisher
  27. Kitahara K, Noguchi Y, Itoh S, Chiba N, Tohyama T, Nagashima K, et al. Complexation behavior of mono- and disaccharides by the vinylbenzeneboronic acid-divinylbenzene copolymer resins packed in a high-performance liquid chromatographic column. J Chromatogr A. 2009;1216:7415-21 pubmed publisher
    ..9. Especially, ribose and talose were totally retained even under acidic and neutral conditions. For the disaccharides, unlike sucrose and maltose, palatinose was completely retained in basic mobile phases. ..
  28. Patáková P, Linhová M, Rychtera M, Paulová L, Melzoch K. Novel and neglected issues of acetone-butanol-ethanol (ABE) fermentation by clostridia: Clostridium metabolic diversity, tools for process mapping and continuous fermentation systems. Biotechnol Adv. 2013;31:58-67 pubmed publisher
    ..99 g/L/h was reached...
  29. Xu W, Zhang W, Zhang T, Jiang B, Mu W. L-Rhamnose isomerase and its use for biotechnological production of rare sugars. Appl Microbiol Biotechnol. 2016;100:2985-92 pubmed publisher
  30. Simon P, Gasparutto D, Gambarelli S, Saint Pierre C, Favier A, Cadet J. Formation of isodialuric acid lesion within DNA oligomers via one-electron oxidation of 5-hydroxyuracil: characterization, stability and excision repair. Nucleic Acids Res. 2006;34:3660-9 pubmed
    ..Moreover, biochemical features dealing with the substrate specificity of several bacterial and yeast base excision repair enzymes to remove isodialuric acid from site-specifically modified DNA fragments were determined. ..
  31. Kishore K, Kanjilal S, Misra S, Reddy C, Murty U. Comparative chemical characterization of pigmented and less pigmented cell walls of Alternaria tenuissima. Curr Microbiol. 2005;51:399-401 pubmed
    ..cell walls were chemically analyzed, no differences were observed in amino-acid composition, hexoses, or pentoses. However, in pigmented cell walls, higher contents of melanin (2...
  32. Capek P, Matulova M. An arabino(glucurono)xylan isolated from immunomodulatory active hemicellulose fraction of Salvia officinalis L. Int J Biol Macromol. 2013;59:396-401 pubmed publisher
    ..NMR and FT-IR measurements, as well as a high negative optical rotation confirmed the ? configuration of glycosidic linkages in AGX backbone. ..
  33. Salonen N, Nyyssölä A, Salonen K, Turunen O. Bifidobacterium longum L-arabinose isomerase--overexpression in Lactococcus lactis, purification, and characterization. Appl Biochem Biotechnol. 2012;168:392-405 pubmed
    ..Using purified B. longum L-AI as the catalyst at 35 °C, equilibrium yields of 36 % D-tagatose and 11 % L-ribulose with 1.67 M D-galactose and L-arabinose, respectively, as the substrates were reached. ..
  34. Peterson K, Cinelli M, Morrell A, Mehta A, Dexheimer T, Agama K, et al. Alcohol-, diol-, and carbohydrate-substituted indenoisoquinolines as topoisomerase I inhibitors: investigating the relationships involving stereochemistry, hydrogen bonding, and biological activity. J Med Chem. 2011;54:4937-53 pubmed publisher
    ..A stereochemical dependence was also observed for carbohydrate-derived indenoisoquinolines. Although similar trends were observed in other classes of Top1 inhibitors, the exact nature of this effect has yet to be elucidated. ..
  35. Freitas B, Morais M, Costa J. Chlorella minutissima cultivation with CO2 and pentoses: Effects on kinetic and nutritional parameters. Bioresour Technol. 2017;244:338-344 pubmed publisher
    ..The objective of this work was to evaluate the effects of using CO2 and pentoses on the growth, protein profile, carbohydrate content and potential ethanol production by fermentation of ..
  36. Gotoh E, Kobayashi Y, Tsuyama M. The post-illumination chlorophyll fluorescence transient indicates the RuBP regeneration limitation of photosynthesis in low light in Arabidopsis. FEBS Lett. 2010;584:3061-4 pubmed publisher
    ..We concluded that PIFT is associated with ribulose-1,5-bisphosphate (RuBP)-regeneration limitation of photosynthesis in low light. ..
  37. Markert M, Scheffler U, Mahrwald R. Asymmetric histidine-catalyzed cross-aldol reactions of enolizable aldehydes: access to defined configured quaternary stereogenic centers. J Am Chem Soc. 2009;131:16642-3 pubmed publisher
    ..Thus, by application of this new methodology, defined-configuration quaternary stereocenters can be constructed with ease. The utility of this method is demonstrated in several total syntheses of branched-chain carbohydrates. ..
  38. Cozier G, Salleh R, Anthony C. Characterization of the membrane quinoprotein glucose dehydrogenase from Escherichia coli and characterization of a site-directed mutant in which histidine-262 has been changed to tyrosine. Biochem J. 1999;340 ( Pt 3):639-47 pubmed appears that, if a hexose is able to bind in the active site, then it is also oxidized, whereas some pentoses are able to bind (and act as competitive inhibitors), but are not substrates...
  39. Remond C, Plantier Royon R, Aubry N, Maes E, Bliard C, O Donohue M. Synthesis of pentose-containing disaccharides using a thermostable alpha-L-arabinofuranosidase. Carbohydr Res. 2004;339:2019-25 pubmed
    ..Importantly, this latter compound is synthesised in a highly regiospecific reaction, which leads to the production of a single disaccharide. ..
  40. Egli M, Pallan P, Pattanayek R, Wilds C, Lubini P, Minasov G, et al. Crystal structure of homo-DNA and nature's choice of pentose over hexose in the genetic system. J Am Chem Soc. 2006;128:10847-56 pubmed
    ..The structure allows a rationalization of the inability of allo-, altro-, and glucopyranosyl-based oligonucleotides to form stable pairing systems. ..
  41. Chung M, Orlova G, Goddard J, Schlaf M, Harris R, Beveridge T, et al. Regioselective silylation of sugars through palladium nanoparticle-catalyzed silane alcoholysis. J Am Chem Soc. 2002;124:10508-18 pubmed
    ..Models for the possible origin of the observed regioselectivity in both silylation methods (silane- and silyl chloride-based) are discussed. ..
  42. Huck J, Roos B, Jakobs C, van der Knaap M, Verhoeven N. Evaluation of pentitol metabolism in mammalian tissues provides new insight into disorders of human sugar metabolism. Mol Genet Metab. 2004;82:231-7 pubmed
    ..We found that the pentoses d-arabinose and d-ribose could cross cell membranes, which indicate possible pentitol formation from ..
  43. Clayton S, Read D, Murray P, Gregory P. Exudation of alcohol and aldehyde sugars from roots of defoliated Lolium perenne L. grown under sterile conditions. J Chem Ecol. 2008;34:1411-21 pubmed publisher
    ..These findings confirm the general finding that repeated defoliation reduces the quantity of total sugars exuded, but the pattern of release of individual sugars is complex and variable. ..
  44. Rivas B, Torre P, Domínguez J, Converti A. Maintenance and growth requirements in the metabolism of Debaryomyces hansenii performing xylose-to-xylitol bioconversion in corncob hemicellulose hydrolyzate. Biotechnol Bioeng. 2009;102:1062-73 pubmed publisher
    ..consisting of carbon material and ATP balances based on five main activities, namely fermentative assimilation of pentoses, semi-aerobic pentose-to-pentitol bioconversion, biomass growth on pentoses, catabolic oxidation of pentoses, and ..
  45. Panagiotou G, Olavarria R, Olsson L. Penicillium brasilianum as an enzyme factory; the essential role of feruloyl esterases for the hydrolysis of the plant cell wall. J Biotechnol. 2007;130:219-28 pubmed
    ..While total release of phenolic acids and pentoses was not observed, the synergistic enhancement of hydrolysis in the presence of feruloyl esterase was clearly ..
  46. Kärkönen A, Murigneux A, Martinant J, Pepey E, Tatout C, Dudley B, et al. UDP-glucose dehydrogenases of maize: a role in cell wall pentose biosynthesis. Biochem J. 2005;391:409-15 pubmed
  47. Wei C, Pohorille A. Permeation of aldopentoses and nucleosides through fatty acid and phospholipid membranes: implications to the origins of life. Astrobiology. 2013;13:177-88 pubmed publisher
    ..The results of this study underscore concerted early evolution of membranes and the biochemical processes that they encapsulated. ..
  48. Heux S, Cadiere A, Dequin S. Glucose utilization of strains lacking PGI1 and expressing a transhydrogenase suggests differences in the pentose phosphate capacity among Saccharomyces cerevisiae strains. FEMS Yeast Res. 2008;8:217-24 pubmed
    ..As a whole, these data highlight a great intraspecies diversity in the PP pathway capacity among S. cerevisiae strains and suggest that a low capacity may be the prime limiting factor in glucose oxidation through this pathway. ..
  49. Zhao J, Xu L, Wang Y, Zhao X, Wang J. [Production of L-lactic acid from pentose by a genetically engineered Escherichia coli]. Wei Sheng Wu Xue Bao. 2013;53:328-37 pubmed
    ..coli JH12, which could efficiently convert glucose and xylose into high-purity L-lactic acid. JH12 could have great potential in industrial fermentation for L-lactic acid production. ..
  50. Su F, Xu K, Zhao B, Tai C, Tao F, Tang H, et al. Genome sequence of the thermophilic strain Bacillus coagulans XZL4, an efficient pentose-utilizing producer of chemicals. J Bacteriol. 2011;193:6398-9 pubmed publisher
    ..Here we present a 2.8-Mb assembly of its genome. Simple and efficient carbohydrate metabolism systems, especially the transketolase/transaldolase pathway, make it possible to convert pentose sugars to products at high levels. ..
  51. Cavener D, Clegg M. Evidence for biochemical and physiological differences between enzyme genotypes in Drosophila melanogaster. Proc Natl Acad Sci U S A. 1981;78:4444-7 pubmed
    ..Higher order phenotypic differences of this kind must be demonstrated to support the hypothesis that natural selection can discriminate among allozymes of a given genetic locus. ..
  52. da Costa E, Moreira A, Nunes F, Coimbra M, Evtuguin D, Domingues M. Differentiation of isomeric pentose disaccharides by electrospray ionization tandem mass spectrometry and discriminant analysis. Rapid Commun Mass Spectrom. 2012;26:2897-904 pubmed publisher
    ..Isomeric pentose disaccharides can be distinguished based on the fragmentation of both [M + Li](+) and [M + Na](+) ions and using different mass spectrometers. However, LIT instrument has a better discriminant power. ..
  53. Andersen Ø, Jordheim M, Byamukama R, Mbabazi A, Ogweng G, Skaar I, et al. Anthocyanins with unusual furanose sugar (apiose) from leaves of Synadenium grantii (Euphorbiaceae). Phytochemistry. 2010;71:1558-63 pubmed publisher
    ..The four former pigments are the first reported anthocyanins containing the monosaccharide apiose, and the three 5'''-cinnamoyl derivative-2''-(beta-apiosyl)-beta-xyloside subunits have previously not been reported for any compound...