Facile synthesis of D-xylulose-5-phosphate and L-xylulose-5-phosphate by xylulokinase-catalyzed phosphorylation

References

• Akinterinwa O, Cirino PC. 2009. Heterologous expression of D-xylulokinase from Pichia stipitis enables high levels of xylitol production by engineered Escherichia coli growing on xylose. Metab Eng. 11:48–55.
   PubMed Web of Science ®Google Scholar
• Anderson RL, Wood WA. 1962. Purification and properties of L-xylulokinase. J Biol Chem. 237:1029–1033.
   PubMed Web of Science ®Google Scholar
• Arrivault S, Guenther M, Fry SC, Fuenfgeld MMFF, Veyel D, Mettler-Altmann T, Stitt M, Lunn JE. 2015. Synthesis and use of stable-isotope-labeled internal standards for quantification of phosphorylated metabolites by LC–MS/MS. Anal Chem. 87:6896–6904.
   PubMed Web of Science ®Google Scholar
• Ashwell G, Hickman J. 1954. Formation of xylulose phosphate from ribose phosphate in spleen extracts. J Am Chem Soc. 76:5889.
   Web of Science ®Google Scholar
• Boyle L, Wamelink MM, Salomons GS, Roos B, Pop A, Dauber A, Hwa V, Andrew M, Douglas J, Feingold M, et al. 2016. Mutations in TKT are the cause of a syndrome including short stature, developmental delay, and congenital heart defects. Am J Hum Genet. 98:1235–1242.
   PubMed Web of Science ®Google Scholar
• Bradford MM. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 72:248–254.
   PubMed Web of Science ®Google Scholar
• Bunker RD, Bulloch EMM, Dickson JMJ, Loomes KM, Baker EN. 2013. Structure and function of human xylulokinase, an enzyme with important roles in carbohydrate metabolism. J Biol Chem. 288:1643–1652.
   PubMed Web of Science ®Google Scholar
• Campos, E, De La Riva, L, Garces, F, Gimenez, R, Aguilar, J, Baldoma, L, Badia, J. 2008. The yiaKLX1X2PQRS and ulaABCDEFG Gene Systems Are Required for the Aerobic Utilization of L-Ascorbate in Klebsiella pneumoniae Strain 13882 with L-Ascorbate-6-Phosphate as the Inducer. Journal of Bacteriology. 190:6615–6624.
   PubMed Web of Science ®Google Scholar
• Del Campo JSM, Chun Y, Kim JE, Patiño R, Zhang Y. 2013. Discovery and characterization of a novel ATP/polyphosphate xylulokinase from a hyperthermophilic Bacterium Thermotoga maritima. J Ind Microbiol Biotechnol. 40:661–669.
   PubMed Web of Science ®Google Scholar
• Deshpande GP, Patterton HG, Essop MF. 2019. The human transketolase-like proteins TKTL1 and TKTL2 are bona fide transketolases. BMC Struct Biol. 19:2–10.
   PubMed Web of Science ®Google Scholar
• Di Luccio E, Petschacher B, Voegtli J, Chou HT, Stahlberg H, Nidetzky B, Wilson DK. 2007. Structural and kinetic studies of induced fit in xylulose kinase from Escherichia coli. J Mol Biol. 365:783–798.
   PubMed Web of Science ®Google Scholar
• Diaz-Moralli S, Ramos-Montoya A, Marin S, Fernandez-Alvarez A, Casado M, Cascante M. 2012. Target metabolomics revealed complementary roles of hexose-and pentose-phosphates in the regulation of carbohydrate-dependent gene expression. Am J Physiol Endocrinol Metab. 303:E234–E242.
   PubMed Web of Science ®Google Scholar
• Dills WL, Parsons PD, Westgate CL, Komplin NJ. 1994. Assay, purification, and properties of bovine liver D-xylulokinase. Protein Exp Purif. 5:259–265.
   PubMed Web of Science ®Google Scholar
• Doten RC, Mortlock RP. 1985. Characterization of xylitol-utilizing mutants of Erwinia uredovora. J Bacteriol. 161:529–533.
   PubMed Web of Science ®Google Scholar
• Gauss D, Schoenenberger B, Molla GS, Kinfu BM, Chow J, Liese A, Streit W, Wohlgemuth R. 2016. Biocatalytic phosphorylation of metabolites in: applied biocatalysis – from fundamental science to industrial applications. In: Liese A, Hilterhaus L, Kettling U, Antranikian G, editors. Weinheim, Germany: Wiley-VCH; p. 147–177.
   Google Scholar
• Gauss D, Schoenenberger B, Wohlgemuth R. 2014. Chemical and enzymatic methodologies for the synthesis of enantiomerically pure glyceraldehyde 3-phosphates. Carbohydr Res. 389:18–24.
   PubMed Web of Science ®Google Scholar
• Guérard-Hélaine C, Debacker M, Clapés P, Szekrenyi A, Hélaine V, Lemaire M. 2014. Efficient biocatalytic processes for highly valuable terminally phosphorylated C5 to C9 D-ketoses. Green Chem. 16:1109–1113.
   Web of Science ®Google Scholar
• Hardt N, Kinfu BM, Chow J, Streit WR, Schoenenberger B, Obkircher M, Wohlgemuth R. 2017. Biocatalytic asymmetric phosphorylation catalyzed by recombinant glycerate-2-kinase. Chem BioChem. 18:1518–1522.
   Google Scholar
• Hemmerlin A, Tritsch D, Hartmann M, Pacaud K, Hoeffler JF, van Dorsselaer A, Rohmer M, Bach TJ. 2006. A cytosolic arabidopsis D-xylulose kinase catalyzes the phosphorylation of 1-deoxy-D-xylulose into a precursor of the plastidial isoprenoid pathway. Plant Physiol. 142:441–457.
   PubMed Web of Science ®Google Scholar
• Hickman J, Ashwell G. 1956. Enzymatic phosphorylation of D-xylulose in liver. J Am Chem Soc. 78:6209.
   Web of Science ®Google Scholar
• Huck JHJ, Struys EA, Verhoeven NM, Jakobs C, van der Knaap MS. 2003. Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectro-metry: application to transaldolase deficiency. Clin Chem. 49:1375–1380.
   PubMed Web of Science ®Google Scholar
• Hurwitz J, Horecker BL. 1956. The purification of phosphoketopentoepimerase from Lactobacillus pentosus and the preparation of xylulose 5-phosphate. J Biol Chem. 223:993–1008.
   PubMed Web of Science ®Google Scholar
• Jin YS, Jones S, Shi NQ, Jeffries TW. 2002. Molecular cloning of XYL3 (D-xylulo-kinase) from Pichia stipitis and characterization of its physiological function. Appl Environ Microbiol. 68:1232–1239.
   PubMed Web of Science ®Google Scholar
• Kabashima T, Kawaguchi T, Wadzinski BE, Uyeda K. 2003. Xylulose 5-phosphate mediates glucose-induced lipogenesis by xylulose 5-phosphate-activated protein phosphatase in rat liver. Proc Natl Acad Sci USA. 100:5107–5112.
   PubMed Web of Science ®Google Scholar
• Kanehisa M, Furumichi M, Tanabe M, Sato Y, Morishima K. 2017. KEGG: new perspectives on genomes, pathways, diseases and drugs. Nucleic Acids Res. 45:D353–D361.
   PubMed Web of Science ®Google Scholar
• Kim JE, Zhang Y. 2016. Biosynthesis of D‐xylulose 5‐phosphate from D‐xylose and polyphosphate through a minimized two‐enzyme cascade. Biotechnol Bioeng. 113:275–282.
   PubMed Web of Science ®Google Scholar
• Kochetov GA, Solovjeva ON. 2014. Structure and functioning mechanism of transketolase. Biochim Biophys Acta. 1844:1608–1618.
   PubMed Web of Science ®Google Scholar
• Komeda H, Yamasaki-Yashiki S, Hoshino K, Asano Y. 2014. Identification and characterization of D-xylulokinase from the D-xylose-fermenting fungus, Mucor circinelloides. FEMS Microbiol Lett. 360:51–61.
   PubMed Web of Science ®Google Scholar
• Krüsemann JL, Lindner SN, Dempfle M, Widmer J, Arrivault S, Debacker M, He H, Kubis A, Chayot R, Anissimova M, et al. 2018. Pathway emergence in central metabolism from three recursive phosphoketolase reactions. Febs J. 285:4367–4377.
   PubMed Web of Science ®Google Scholar
• Laemmli UK. 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature. 227:680–685.
   PubMed Web of Science ®Google Scholar
• Meile L, Rohr LM, Geissmann TA, Herensperger M, Teuber M. 2001. Characterization of the D-xylulose 5-phosphate/D-fructose 6-phosphate phosphoketolase gene (xfp) from Bifidobacterium lactis. J Bacteriol. 183:2929–2936.
   PubMed Web of Science ®Google Scholar
• Mocali A, Aldinucci D, Paoletti F. 1985. Preparative enzymic synthesis and isolation of D-threo-2-pentulose 5-phosphate (D-xylulose 5-phosphate). Carbohydr Res. 143:288–293.
   Web of Science ®Google Scholar
• Molla GS, Kinfu BM, Chow J, Streit W, Wohlgemuth R, Liese A. 2017. Bioreaction engineering leading to efficient synthesis of L‐glyceraldehyd‐3‐phosphate. Biotechnol J. 12:1600625.
   Web of Science ®Google Scholar
• Nishimura M, Uyeda K. 1995. Purification and characterization of a novel xylulose 5-phosphate-activated protein phosphatase catalyzing dephosphorylation of fructose-6-phosphate,2-kinase: fructose-2,6-bisphosphatase. J Biol Chem. 270:26341–26346.
   PubMed Web of Science ®Google Scholar
• Pival, SL, Birner-Gruenberger, R, Krump, C, Nidetzky, B. 2011. D-Xylulose kinase from Saccharomyces cerevisiae: Isolation and characterization of the highly unstable enzyme, recombinantly produced in Escherichia coli. Protein Expression and Purification. 79:223–230.
   PubMed Web of Science ®Google Scholar
• Povelainen M, Eneyskaya EV, Kulminskaya AA, Ivanen DR, Kalkkinen N, Neustroev KN, Miasnikov AN. 2003. Biochemical and genetic characterization of a novel enzyme of pentitol metabolism: D-arabitol-phosphate dehydrogenase. Biochem J. 371:191–197.
   PubMed Web of Science ®Google Scholar
• Povelainen M, Miasnikov AN. 2007. Production of xylitol by metabolically engineered strains of Bacillus subtilis. J Biotechnol. 128:24–31.
   PubMed Web of Science ®Google Scholar
• Radek A, Müller MF, Gätgens J, Eggeling L, Krumbach K, Marienhagen J, Noack S. 2016. Formation of xylitol and xylitol-5-phosphate and its impact on growth of d-xylose-utilizing Corynebacterium glutamicum strains. J Biotechnol. 231:160–166.
   PubMed Web of Science ®Google Scholar
• Rodriguez-Peña MJ, Cid VJ, Arroyo J, Nombela C. 1998. The YGR194c (XKS1) gene encodes the xylulokinase from the budding yeast Saccharomyces cerevisiae. FEMS Microbiol Lett. 162:155–160.
   PubMed Web of Science ®Google Scholar
• Sanchez JC, Gimenez R, Schneider A, Fessner WD, Baldomà L, Aguilar J, Badia J. 1994. Activation of a cryptic gene encoding a kinase for L-xylulose opens a new pathway for the utilization of L-lyxose by Escherichia coli. J Biol Chem. 269:29665–29669.
   PubMed Web of Science ®Google Scholar
• Shaeri J, Wohlgemuth R, Woodley JM. 2006. Semiquantitative process screening for the biocatalytic synthesis of D-xylulose-5-phosphate. Org Process Res Dev. 10:605–610.
   Web of Science ®Google Scholar
• Shaeri J, Wright I, Rathbone EB, Wohlgemuth R, Woodley JM. 2008. Characterization of enzymatic D-xylulose 5-phosphate synthesis . Biotechnol Bioeng. 101:761–767.
   PubMed Web of Science ®Google Scholar
• Shi R, Pineda M, Ajamian E, Cui Q, Matte A, Cygler M. 2008. Structure of L-xylulose-5-phosphate 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.
   PubMed Web of Science ®Google Scholar
• Simpson FJ, Bhuyan BK. 1962. Enzymatic preparation of D-xylulose 5-phosphate. Can J Microbiol. 8:663–672.
   Web of Science ®Google Scholar
• Soliman MA, Rahman AMA, Lamming DA, Birsoy K, Pawling J, Frigolet ME, Lu H, Fantus IG, Pasculescu A, Zheng Y, et al. 2014. The adaptor protein p66Shc inhibits mTOR-dependent anabolic metabolism. Sci Signal. 7: ra17.
   PubMed Web of Science ®Google Scholar
• Solovjeva ON, Kochetov GA. 2008. Enzymatic synthesis of D-xylulose 5-phosphate from hydroxypyruvate and D-glyceraldehyde-3-phosphate. J Mol Catal B: Enzymatic. 54:90–92.
   Google Scholar
• Sprenger GA, Schörken U, Sprenger G, Sahm H. 1995. Transketolase A of Escherichia coli K12. Purification and properties of the enzyme from recombinant strains. Eur J Biochem. 230:525–532.
   PubMedGoogle Scholar
• Srere PA, Cooper JR, Klybas V, Racker E. 1955. Xylulose-5-phosphate, a new intermediate in the pentose phosphate cycle. Arch Biochem Biophys. 59:535–538.
   PubMed Web of Science ®Google Scholar
• Srere P, Cooper JR, Tabachnick M, Racker E. 1958. The oxidative pentose phosphate cycle. I. Preparation of substrates and enzymes. Arch Biochem Biophys. 74:295–305.
   PubMed Web of Science ®Google Scholar
• Studier FW, Moffatt BA. 1986. Use of bacteriophage T7 RNA polymerase to direct selective high-level expression of cloned genes. J Mol Biol. 189:113–130.
   PubMed Web of Science ®Google Scholar
• Stumpf PK, Horecker BL. 1956. The role of xylulose 5-phosphate in xylose metabolism of Lactobacillus pentosus. J Biol Chem. 218:753–768.
   PubMed Web of Science ®Google Scholar
• Uyeda K, Repa JJ. 2006. Carbohydrate response element binding protein, ChREBP, a transcription factor coupling hepatic glucose utilization and lipid synthesis. Cell Metab. 4:107–110.
   PubMed Web of Science ®Google Scholar
• Van Kuyk PA, de Groot MJL, Ruijter GJG, de Vries RP, Visser J. 2001. The Aspergillus niger D-xylulose gene is co-expressed with genes encoding arabinan degrading enzymes, and is essential for growth on D-xylose and L-arabinose. Eur J Biochem. 268:5414–5423.
   PubMedGoogle Scholar
• Wei WC, Chang CC. 2017. Chemical synthesis of ketopentose‐5‐phosphates. Eur J Org Chem. 21:3033–3040.
   Web of Science ®Google Scholar
• Wen L, Huang K, Liu Y, Wang PG. 2016. Facile enzymatic synthesis of phosphorylated ketopentoses. ACS Catal. 6:1649–1654.
   Web of Science ®Google Scholar
• Wohlgemuth R, Liese A, Streit W. 2017. Biocatalytic phosphorylations of metabolites: past, present, and future. Trends Biotechnol. 35:452–465.
   PubMed Web of Science ®Google Scholar
• Wood T. 1973. The preparation of xylulose 5-phosphate using transketolase. Prep Biochem. 3:509–515.
   PubMed Web of Science ®Google Scholar
• Wu X, Hou J, Chen X, Chen X, Zhao W. 2016. Identification and functional analysis of the L-ascorbate-specific enzyme II complex of the phosphotransferase system in Streptococcus mutans. BMC Microbiol. 16:1–11.
   PubMed Web of Science ®Google Scholar
• Wungsintaweekul J, Herz S, Hecht S, Eisenreich W, Feicht R, Rohdich F, Bacher A, Zenk M. 2001. Phosphorylation of 1-deoxy-D-xylulose by D-xylulokinase of Escherichia coli. Eur J Biochem. 268:310–316.
   PubMedGoogle Scholar
• Yew WS, Akana J, Wise EL, Rayment I, Gerlt JA. 2005. Evolution of enzymatic activities in the orotidine 5'-monophosphate decarboxylase suprafamily: enhancing the promiscuous D-arabino-hex-3-ulose 6-phosphate synthase reaction catalyzed by 3-keto-L-gulonate 6-phosphate decarboxylase. Biochemistry. 44:1807–1815.
   PubMed Web of Science ®Google Scholar
• Yew WS, Gerlt JA. 2002. Utilization of L-ascorbate by Escherichia coli K-12: assignments of functions to products of the yjf-sga and yia-sgb operons. J Bacteriol. 184:302–306.
   PubMed Web of Science ®Google Scholar
• Yew WS, Wise EL, Rayment I, Gerlt JA. 2004. Evolution of enzymatic activities in the orotidine 5'-monophosphate decarboxylase suprafamily: mechanistic evidence for a proton relay system in the active site of 3-keto-L-gulonate 6-phosphate decarboxylase. Biochemistry. 43:6427–6437.
   PubMed Web of Science ®Google Scholar
• Zimmermann FT, Schneider A, Schörken U, Sprenger GA, Fessner WD. 1999. Efficient multi-enzymatic synthesis of D-xylulose 5-phosphate. Tetrahedron: Asymmetry. 10:1643–1646.
   Google Scholar