DOCSLIB.ORG

Efficient Production of 2-Deoxyribose 5-Phosphate From

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Efficient Production of 2-Deoxyribose 5-Phosphate From Biosci. Biotechnol. Biochem., 70 (6), 1371–1378, 2006 Efficient Production of 2-Deoxyribose 5-Phosphate from Glucose and Acetaldehyde by Coupling of the Alcoholic Fermentation System of Baker’s Yeast and Deoxyriboaldolase-Expressing Escherichia coli y Nobuyuki HORINOUCHI,1 Jun OGAWA,1; Takako KAWANO,1 Takafumi SAKAI,1 Kyota SAITO,1 Seiichiro MATSUMOTO,2 Mie SASAKI,2 Yoichi MIKAMI,2 and Sakayu SHIMIZU1 1Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, Sakyo-ku, Kyoto 606-8502, Japan 2Tokyo Laboratory, Yuki Gosei Kogyo Co., Ltd., 3-37-1 Sakashita, Itabashi-ku, Tokyo 174-0043, Japan Received December 5, 2005; Accepted February 19, 2006; Online Publication, June 23, 2006 [doi:10.1271/bbb.50648] 2-Deoxyribose 5-phosphate production through cou- of Klebsiella pneumoniae B-4-4 with triosephosphates pling of the alcoholic fermentation system of baker’s such as D-glyceraldehyde 3-phosphate (G3P) and dihy- yeast and deoxyriboaldolase-expressing Escherichia coli droxyacetone phosphate (DHAP) and acetaldehyde as was investigated. In this process, baker’s yeast generates starting materials.8) Triosephosphates are the intermedi- fructose 1,6-diphosphate from glucose and inorganic ates of glycolysis, so if triosephosphates are supplied phosphate, and then the E. coli convert the fructose 1,6- through glycolysis from cheap sugars, the process diphosphate into 2-deoxyribose 5-phosphate via D-glyc- should become more practical. In a previous study,9) eraldehyde 3-phosphate. Under the optimized condi- we investigated the glycolytic function of DERA- tions with toluene-treated yeast cells, 356 mM (121 g/l) expressing E. coli with several intermediates of glycol- fructose 1,6-diphosphate was produced from 1,111 mM ysis, such as glucose, fructose, fructose 6-phosphate, and glucose and 750 mM potassium phosphate buffer (pH fructose 1,6-diphosphate (FDP), and found that the 6.4) with a catalytic amount of AMP, and the reaction phosphorylated intermediates, especially FDP, served as supernatant containing the fructose 1,6-diphosphate was suitable precursors for G3P. used directly as substrate for 2-deoxyribose 5-phosphate Processes for the production of various substances production with the E. coli cells. With 178 mM enzy- through coupling with the powerful fermentative ability matically prepared fructose 1,6-diphosphate and 400 of baker’s yeast as the energy source were established by mM acetaldehyde as substrates, 246 mM (52.6 g/l) 2- Tochikura and colleagues.10–12) The sugar-fermentative deoxyribose 5-phosphate was produced. The molar yield system of baker’s yeast was used as the ATP donor in of 2-deoxyribose 5-phosphate as to glucose through the these processes. Temporary accumulation of FDP in the total two step reaction was 22.1%. The 2-deoxyribose course of ATP regeneration has been reported.13–15) 5-phosphate produced was converted to 2-deoxyribose Based on these reports, we designed a novel meta- with a molar yield of 85% through endogenous or bolic and enzymatic DR5P production system consisting exogenous phosphatase activity. of glucose fermentation and DERA-catalyzed aldol condensation with glucose and acetaldehyde as starting Key words: 2-deoxyribose 5-phosphate; 2-deoxyribose; materials. In this study, we tried to optimize FDP deoxyriboaldolase; alcoholic fermentation; production from glucose and inorganic phosphate with 20-deoxyribonucleoside toluene-treated baker’s yeast (toluene-treated yeast), and DR5P production from enzymatically prepared FDP and The synthesis of antiviral 20-deoxyribonucleosides acetaldehyde by DERA-expressing E. coli (Fig. 1). such as AZT requires a deoxyribose component as a Further convenient conversion of DR5P to 2-deoxyri- starting material, but chemical synthesis of the deoxy- bose (DR) was also examined. ribose frame is a tedious process with many protection and deprotection steps.1–4) Materials and Methods We performed 2-deoxyribose 5-phosphate (DR5P) production by means of deoxyriboaldolase 5–7) (DERA) Preparation of a toluene-treated yeast. Pressed y To whom correspondence should be addressed. Tel: +81-75-753-6122; Fax: +81-75-753-6128; E-mail: [email protected] Abbreviations: DR5P, 2-deoxyribose 5-phosphate; DERA, deoxyriboaldolase; FDP, fructose 1,6-diphosphate; G3P, D-glyceraldehyde 3-phosphate; DHAP, dihydroxyacetone phosphate; LB, Luria-Bertani; DR, 2-deoxyribose 1372 N. HORINOUCHI et al. ATP ATP ADP ADP AMP AMP Glucose FDP ADP ATP CH OH 2 O O P O HO O P OH OH Ethanol, CO2 HO OH OH HO Pi Pi Baker's yeast FDP O OH DERA CHO CH OH P O 2 CHOH C=O HO CH2O P CH2O P DR5P G3P DHAP DERA-expressing CH3CHO E. coli Fig. 1. DR5P Synthesis from Glucose and Acetaldehyde through the Fermentation Energy of Baker’s Yeast and DERA-Expressing E. coli. baker’s yeast (Oriental Yeast, Tokyo) was incubated resulting supernatants were measured as described with 16.6% (v/v) toluene in 176 mM potassium phos- below after checking the accumulation of DR by TLC. phate buffer (pH 7.0) at 37 C for 1 h with standing. The The averages of three separate experiments, which were suspension was centrifuged (3;500 Â g, 20 min), and the reproducible within Æ 10%, are presented in the text resulting pellet was used as the source of glycolytic and figures. enzymes (toluene-treated yeast). DR production: DR production was carried out by means of temperature shift or phosphatase addition. As Culture conditions for DERA-expressing E. coli. for temperature shift, the complete reaction mixture for DERA-expressing E. coli 10B5/pTS8 was cultivated DR5P production was further incubated at 47 C for at 37 C in Luria-Bertani (LB) medium (1% peptone, 22 h and centrifuged (15;000 Â g, 15 min), and then the 0.5% yeast extract, 1% NaCl, pH 7.2) for 12 h. Cells amount of DR in the resulting supernatant was assayed. were harvested by centrifugation (8;000 Â g, 10 min). As for phosphatase addition, the reaction mixture for After washing with a 0.85% NaCl solution, the cells DR5P production was centrifuged (15;000 Â g, 15 min), were used for DR5P synthesis. and the resulting supernatant was incubated at 80 C for 1 h, and then 2% (w/v) of Sumizyme PM (Shin Nihon Reaction conditions. FDP production: The standard Chemical, Anjo, Japan) was added. After 4 h incubation reaction mixture comprised, in 10 ml, 1,111 mM glucose, at 37 C, the reaction mixture was centrifuged (15;000 Â 500 mM K2HPO4,30mM MgSO4.7H2O, 15 mM AMP. g, 15 min) and the amount of DR in the supernatant was 2Na and 60% (w/v) toluene-treated yeast. The reactions determined. The averages of three separate experiments, were carried out at 37 C for 3–7 h with standing. The which were reproducible within Æ 10%, are presented supernatants obtained on centrifugation (15;000 Â g, in the text. 15 min) were subjected to FDP analysis and then used for DR5P production as an enzymatically prepared FDP Analytical methods. FDP analysis: FDP was measured solution. The averages of three separate experiments, enzymatically by monitoring a decrease in absorbance at which were reproducible within Æ 10%, are presented 340 nm of NADH through coupled reactions catalyzed in the text and figures. by FDP aldolase, triosephosphate isomerase (TPI), and DR5P production: The standard reaction mixture a-glycerophosphate dehydrogenase (GDH). Twenty ml comprised, in 0.5–60 ml, 50% (v/v) enzymatically of FDP-containing sample solution was added to 140 ml prepared FDP solution, 200 mM acetaldehyde, 200 mM of a reaction mixture comprising 150 mM Tris/HCl potassium phosphate buffer (pH 7.0), 15 mM MgSO4. (pH 7.4) and 0.5 mM NADH. Then 20 ml of a TPI/GDH 7H2O, 0.4% (v/v) polyoxyethylenelaurylamine, 1.0% solution (Sigma, St. Louis, MO) containing 50 U of TPI (v/v) xylene, and 12.5% (w/v) wet cells of E. coli and 5 U of GDH was added to decompose contaminating 10B5/pTS8. The reactions were carried out at 28 C for triosephosphates. After 10 min incubation at 30 C, 20 ml 2–4 h with shaking (120 rpm), followed by centrifuga- of FDP aldolase solution (Sigma) containing 10 U of tion (15;000 Â g, 15 min). The amounts of DR5P in the FDP aldolase from rabbit muscle was added, and then Enzymatic 2-Deoxyribose 5-Phosphate Production 1373 ) A M 250 mM Pi 500 mM Pi 750 mM Pi1000 mM Pi 1250 mM Pi 450 300 150 FDP production (m 0 357 7 357 357 35 357 Reaction time (h) ) M B 250 mM Pi 500 mM Pi 750 mM Pi1000 mM Pi 1250 mM Pi 160 120 80 40 0 DR5P production (m 3 h 5 h 7 h 3 h 5 h 7 h 3 h 5 h 7 h 3 h 5 h 7 h 3 h 5 h 7 h Reaction time for FDP production Fig. 2. Effects of the Inorganic Phosphate Concentration on FDP (A) and DR5P (B) Production. A, The reactions were carried out in 10 ml under the standard conditions, except for the inorganic phosphate concentration, for 7 h. B, The reaction mixtures, comprising in 300 ml 25% (v/v) enzymatically prepared FDP solution (with various initial inorganic phosphate concentrations and reaction times), 200 mM KH2PO4,15mM MgSO4.7H2O, 0.4% (v/v) polyoxyethylenelaurylamine, and 1% (v/v) xylene, were incubated at 28 C for 2 h with shaking (120 rpm). Pi, inorganic phosphate. the decrease in NADH was monitored at a wavelength of Result 340 nm with a Spectra Max 190 (Molecular Devices, Sunnyvale, CA) after 20 min incubation at 30 C. The Optimization of FDP production with baker’s yeast FDP concentration was calculated based on the decrease Reaction pH and temperature: The effect of the in NADH using a calibration curve obtained with reaction pH (in a range of 6.0–9.0) and temperature (in a authentic FDP solutions of known concentrations.
Load more

Recommended publications
  • Xylose Fermentation to Ethanol by Schizosaccharomyces Pombe Clones with Xylose Isomerase Gene." Biotechnology Letters (8:4); Pp
    NREL!TP-421-4944 • UC Category: 246 • DE93000067 l I Xylose Fermenta to Ethanol: A R ew '.) i I, -- , ) )I' J. D. McMillan I ' J.( .!i �/ .6' ....� .T u�.•ls:l ., �-- • National Renewable Energy Laboratory II 'J 1617 Cole Boulevard Golden, Colorado 80401-3393 A Division of Midwest Research Institute Operated for the U.S. Department of Energy under Contract No. DE-AC02-83CH10093 Prepared under task no. BF223732 January 1993 NOTICE This report was prepared as an account of work sponsored by an agency of the United States government. Neither the United States government nor any agency thereof, nor any of their employees, makes any warranty, express or implied, or assumes any legal liability or responsibility for the accuracy, com­ pleteness, or usefulness of any information, apparatus, product, or process disclosed, or represents that its use would not infringe privately owned rights. Reference herein to any specific commercial product, process, or service by trade name, trademark, manufacturer, or otherwise does not necessarily con­ stitute or imply its endorsement, recommendation, or favoring by the United States government or any agency thereof. The views and opinions of authors expressed herein do not necessarily state or reflect those of the United States government or any agency thereof. Printed in the United States of America Available from: National Technical Information Service U.S. Department of Commerce 5285 Port Royal Road Springfield, VA22161 Price: Microfiche A01 Printed Copy A03 Codes are used for pricing all publications. The code is determined by the number of pages in the publication. Information pertaining to the pricing codes can be found in the current issue of the following publications which are generally available in most libraries: Energy Research Abstracts (ERA); Govern­ ment Reports Announcements and Index ( GRA and I); Scientific and Technical Abstract Reports(STAR); and publication NTIS-PR-360 available from NTIS at the above address.
    [Show full text]
  • PENTOSE PHOSPHATE PATHWAY — Restricted for Students Enrolled in MCB102, UC Berkeley, Spring 2008 ONLY
    Metabolism Lecture 5 — PENTOSE PHOSPHATE PATHWAY — Restricted for students enrolled in MCB102, UC Berkeley, Spring 2008 ONLY Bryan Krantz: University of California, Berkeley MCB 102, Spring 2008, Metabolism Lecture 5 Reading: Ch. 14 of Principles of Biochemistry, “Glycolysis, Gluconeogenesis, & Pentose Phosphate Pathway.” PENTOSE PHOSPHATE PATHWAY This pathway produces ribose from glucose, and it also generates 2 NADPH. Two Phases: [1] Oxidative Phase & [2] Non-oxidative Phase + + Glucose 6-Phosphate + 2 NADP + H2O Ribose 5-Phosphate + 2 NADPH + CO2 + 2H ● What are pentoses? Why do we need them? ◦ DNA & RNA ◦ Cofactors in enzymes ● Where do we get them? Diet and from glucose (and other sugars) via the Pentose Phosphate Pathway. ● Is the Pentose Phosphate Pathway just about making ribose sugars from glucose? (1) Important for biosynthetic pathways using NADPH, and (2) a high cytosolic reducing potential from NADPH is sometimes required to advert oxidative damage by radicals, e.g., ● - ● O2 and H—O Metabolism Lecture 5 — PENTOSE PHOSPHATE PATHWAY — Restricted for students enrolled in MCB102, UC Berkeley, Spring 2008 ONLY Two Phases of the Pentose Pathway Metabolism Lecture 5 — PENTOSE PHOSPHATE PATHWAY — Restricted for students enrolled in MCB102, UC Berkeley, Spring 2008 ONLY NADPH vs. NADH Metabolism Lecture 5 — PENTOSE PHOSPHATE PATHWAY — Restricted for students enrolled in MCB102, UC Berkeley, Spring 2008 ONLY Oxidative Phase: Glucose-6-P Ribose-5-P Glucose 6-phosphate dehydrogenase. First enzymatic step in oxidative phase, converting NADP+ to NADPH. Glucose 6-phosphate + NADP+ 6-Phosphoglucono-δ-lactone + NADPH + H+ Mechanism. Oxidation reaction of C1 position. Hydride transfer to the NADP+, forming a lactone, which is an intra-molecular ester.
    [Show full text]
  • Production of Natural and Rare Pentoses Using Microorganisms and Their Enzymes
    EJB Electronic Journal of Biotechnology ISSN: 0717-3458 Vol.4 No.2, Issue of August 15, 2001 © 2001 by Universidad Católica de Valparaíso -- Chile Received April 24, 2001 / Accepted July 17, 2001 REVIEW ARTICLE Production of natural and rare pentoses using microorganisms and their enzymes Zakaria Ahmed Food Science and Biochemistry Division Faculty of Agriculture, Kagawa University Kagawa 761-0795, Kagawa-Ken, Japan E-mail: [email protected] Financial support: Ministry of Education, Science, Sports and Culture of Japan under scholarship program for foreign students. Keywords: enzyme, microorganism, monosaccharides, pentose, rare sugar. Present address: Scientific Officer, Microbiology and Biochemistry Division, Bangladesh Jute Research Institute, Shere-Bangla Nagar, Dhaka- 1207, Bangladesh. Tel: 880-2-8124920. Biochemical methods, usually microbial or enzymatic, murine tumors and making them useful for cancer treatment are suitable for the production of unnatural or rare (Morita et al. 1996; Takagi et al. 1996). Recently, monosaccharides. D-Arabitol was produced from D- researchers have found many important applications of L- glucose by fermentation with Candida famata R28. D- arabinose in medicine as well as in biological sciences. In a xylulose can also be produced from D-arabitol using recent investigation, Seri et al. (1996) reported that L- Acetobacter aceti IFO 3281 and D-lyxose was produced arabinose selectively inhibits intestinal sucrase activity in enzymatically from D-xylulose using L-ribose isomerase an uncompetitive manner and suppresses the glycemic (L-RI). Ribitol was oxidized to L-ribulose by microbial response after sucrose ingestion by such inhibition. bioconversion with Acetobacter aceti IFO 3281; L- Furthermore, Sanai et al. (1997) reported that L-arabinose ribulose was epimerized to L-xylulose by the enzyme D- is useful in preventing postprandial hyperglycemia in tagatose 3-epimerase and L-lyxose was produced by diabetic patients.
    [Show full text]
  • (SIRE) Followed by Back-Extraction (BE) Process for Efficient Fermentation of Ketose Sugars to Products
    A Dissertation entitled Optimizing Simultaneous-Isomerization-and-Reactive-Extraction (SIRE) Followed by Back-Extraction (BE) Process for Efficient Fermentation of Ketose Sugars to Products by Peng Zhang Submitted to the Graduate Faculty as partial fulfillment of the requirements for the Doctor of Philosophy Degree in Biomedical Engineering ________________________________________ Dr. Patricia Relue, Co-Committee Chair ________________________________________ Dr. Sasidhar Varanasi, Co-Committee Chair ________________________________________ Dr. Sridhar Viamajala, Committee Member ________________________________________ Dr. Stephen Callaway, Committee Member ________________________________________ Dr. Randall Ruch, Committee Member ________________________________________ Dr. Amanda Bryant-Friedrich, Dean College of Graduate Studies The University of Toledo May 2018 Copyright 2018, Peng Zhang This document is copyrighted material. Under copyright law, no parts of this document may be reproduced without the expressed permission of the author. An Abstract of Optimizing Simultaneous-Isomerization-and-Reactive-Extraction (SIRE) Followed by Back-Extraction (BE) Process for Efficient Fermentation of Ketose Sugars to Products by Peng Zhang Submitted to the Graduate Faculty as partial fulfillment of the requirements for the Doctor of Philosophy Degree in Biomedical Engineering The University of Toledo May 2018 Lignocellulosic biomass is an abundant, inexpensive feedstock. It is mostly composed of cellulose (38-50% of the dry mass) and hemicellulose
    [Show full text]
  • A Dynamic Flux Balance Model and Bottleneck Identification of Glucose, Xylose, Xylulose Co-Fermentation in Saccharomyces Cerevis
    10849 Bioresource Technology 188 (2015) 153–160 Contents lists available at ScienceDirect Bioresource Technology journal homepage: www.elsevier.com/locate/biortech A dynamic flux balance model and bottleneck identification of glucose, xylose, xylulose co-fermentation in Saccharomyces cerevisiae ⇑ William Hohenschuh a, Ronald Hector b, Ganti S. Murthy a, a Oregon State University, United States b USDA, ARS, NCAUR, United States highlights graphical abstract Xylulose utilization limited by Boleneck Idenficaon for Xylulose Ulizaon in S. cerevisiae phosphorylation by xylulokinase in Hemicellulose wt S. cerevisiae. XI Transport limits xylulose utilization Cellobiose Glucose in xylulokinase enhanced strains. NADP(H) Xylose XR HXT family of transporters NADP+ Xylitol XDH NAD+ responsible for xylulose transport in Xylulose NADH XK S. cerevisiae. Cellulose Pentose Phosphate Pathway Accounting for cell death produces improved modeling fit of batch Glycolysis fermentation. S. cerevisiae Ethanol article info abstract Article history: A combination of batch fermentations and genome scale flux balance analysis were used to identify and Received 25 November 2014 quantify the rate limiting reactions in the xylulose transport and utilization pathway. Xylulose phospho- Received in revised form 4 February 2015 rylation by xylulokinase was identified as limiting in wild type Saccharomyces cerevisiae, but transport Accepted 5 February 2015 became limiting when xylulokinase was upregulated. Further experiments showed xylulose transport Available online 20 February 2015 through the HXT family of non-specific glucose transporters. A genome scale flux balance model was developed which included an improved variable sugar uptake constraint controlled by HXT expression. Keywords: Model predictions closely matched experimental xylulose utilization rates suggesting the combination Xylose of transport and xylulokinase constraints is sufficient to explain xylulose utilization limitation in S.
    [Show full text]
  • Production of Prebiotic Exopolysaccharides by Lactobacilli
    Lehrstuhl für Technische Mikrobiologie Production of prebiotic exopolysaccharides by lactobacilli Markus Tieking Vollständiger Abdruck der von der Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt der Technischen Universität München zur Erlangung des akademischen Grades eines Doktor - Ingenieurs genehmigten Dissertation. Vorsitzender: Univ.-Prof. Dr.- Ing. E. Geiger Prüfer der Dissertation: 1. Univ.-Prof. Dr. rer. nat. habil. R. F. Vogel 2. Univ.-Prof. Dr.- Ing. D. Weuster-Botz Die Dissertation wurde am 09.03.2005 bei der Technischen Universität eingereicht und durch die Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt am 27.05.2005 angenommen. Lehrstuhl für Technische Mikrobiologie Production of prebiotic exopolysaccharides by lactobacilli Markus Tieking Doctoral thesis Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt Freising 2005 Mein Dank gilt meinem Doktorvater Prof. Rudi Vogel für die Überlassung des Themas sowie die stete Diskussionsbereitschaft, Dr. Michael Gänzle für die kritische Begleitung, die ständige Diskussionsbereitschaft sowie sein fachliches Engagement, welches weit über das übliche Maß hinaus geht, Dr. Matthias Ehrmann für seine uneingeschränkte Bereitwilligkeit, sein Wissen auf dem Gebiet der Molekularbiologie weiterzugeben, seine unschätzbar wertvollen praktischen Ratschläge auf diesem Gebiet sowie für seine Geduld, meiner lieben Frau Manuela, deren Motivationskünste und emotionale Unterstützung mir wissenschaftliche
    [Show full text]
  • Studies on the Prebiotic Origin of 2-Deoxy-D-Ribose
    Studies on the Prebiotic Origin of 2-Deoxy-D-ribose Andrew Mark Steer Doctor of Philosophy University of York Chemistry August 2017 Abstract DNA is an important biological structure necessary for cell proliferation. The origins of cell- like structures and the building blocks of DNA are therefore also of great concern. As of yet the prebiotic origin of 2-deoxy-D-ribose, the sugar of DNA, has no satisfactory explanation. This research attempts to provide a possible explanation to the chemical origin of 2-deoxy- D-ribose via an aldol reaction between acetaldehyde 1 and D-glyceraldehyde D-2 (Error! Reference source not found.). The sugar mixture is trapped with N,N-diphenylhydrazine 3 for ease of purification and characterisation. The reaction is promoted by amino acids, amino esters and amino nitriles consistently giving selectivities in favour of 2-deoxy-D- ribose. This is the first example of an amino nitrile promoted reaction. Potential prebiotic synthesis of 2-deoxy-D-ribose and subsequent trapping with N,N-diphenyl hydrazine 3. The research is developed further by exploring the formation of 2-deoxy-D-ribose in a “protocell” environment – a primitive cell. Here we suggest that primitive cells may have been simple hydrogel systems. A discussion of the characterisation and catalytic ability of small peptide-based supramolecular structures is included. ii Contents Abstract ............................................................................................................................ ii Contents .........................................................................................................................
    [Show full text]
  • Isomerization of Aldo-Pentoses Into Keto-Pentoses Catalyzed by Phosphates
    Electronic Supplementary Material (ESI) for Green Chemistry. This journal is © The Royal Society of Chemistry 2017 Isomerization of aldo-pentoses into keto-pentoses catalyzed by phosphates Irina Delidovich,*a Maria S. Gyngazova,a Nuria Sánchez-Bastardo,b Julia P. Wohland,a Corinna Hoppea and Peter Draboa aChair of Heterogeneous Catalysis and Chemical Technology, RWTH Aachen University, Worringerweg 2, 52074 Aachen, Germany. E-mail: [email protected] bHigh Pressure Processes Group, Chemical Engineering and Environmental Technology Department, Escuela de Ingenierías Industriales, University of Valladolid, 47011 Valladolid, Spain Fig. 1S Equilibrium constants of the isomerization reactions (left) and equilibrium yields (right) of keto-pentoses as functions of temperature according to the thermodynamic data reported by Tewari et al.1, 2 S1 13CHO CH2OH 13 CHO Glycolaldehyde H C OH Retro aldol + H C OH CH2OH H C OH CHO Isomerization CH2OH Aldol C O CH2OH H C OH C O H C OH Ribose CH OH 13CHO 13 CH2OH 2 + H C OH Dihydroxyacetone CH2OH Glyceraldehyde CH2OH Ribulose 13 CH2OH 13 CH2OH CH2OH 13 13 C O CHO CH2OH C O C O CH2OH 13 H C OH Isomerization C O Retro aldol Aldol H C OH H C OH Dihydroxyacetone + H C OH H C OH H C OH + H C OH H C OH H C OH CH OH CH OH CHO 2 2 CH2OH CH2OH Ribulose Ribulose CH OH Ribose Ribulose 2 Glycolaldehyde Scheme 1S. Isotope label scrambling with D-(1-13C)-ribose as a substrate via consecutive retro aldol and aldol reactions. According to the previously published data, isomerization of glyceraldehyde into dihydroxyacetone (shown in the upper sequence of reactions) is highly favorable in the presence of 3 NaH2PO4+Na2HPO4.
    [Show full text]
  • CH 460 Dr. Muccio Worksheet 4 1. What Is the Difference Between An
    CH 460 Dr. Muccio Worksheet 4 1. What is the difference between an aldose and a ketose? 2. What is the oxidation number of the carbon on the following 3 groups? 3. Circle the carbons in the figure below that are chiral. How many isomers does this molecule have? 4. What is the difference between an epimer and an enantiomer? 5. How is the Fisher projection of D-glucose converted to L-glucose? 6. The chemical formula of a tetrose monosaccharide is _____. a. C6H12O6 b.C4H10O4 c.C6H10O4 d.C4H8O4 e.None 7. Match the carbohydrates to their descriptions on the left. i. D-Glyceraldehyde _____ A. C-2 Epimer of Glucose ii. D-Threose _____ B. C-2 Epimer of Threose iii. D-Ribose _____ C. Pentose with D,D,D stereochem iv. D-Mannose _____ D. Triose v. D-Galactose _____ E. Hexose with DLDD stereochem vi. D-Erythrose _____ F. C-3 Epimer of Ribose vii. D-Xylose _____ G. C-4 Epimer of Glucose viii. D-Glucose _____ H. C-2 Epimer of Erythrose ix. D-Arabinose _____ I. C-2 Epimer of Ribose x. D-Fructose _____ J. Ketose of Letter D xi. D-Xylulose _____ K. Ketose of Letter F xii. D-Erythrulose _____ L. Enantiomer of Letter A xiii. Dihydroxyacetone ____ M. Ketose of Letter B xiv. D-Ribulose _____ N. Ketose of Letter E xv. L-Mannose _____ O. Ketose of Letter C CH 460 Dr. Muccio Worksheet 4 8. In the conversion of aldoses to their ketoses, the _____ carbon loses its stererochemistry.
    [Show full text]
  • Title Production of Rare Sugars from Common Sugars In
    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Kyoto University Research Information Repository Production of rare sugars from common sugars in subcritical Title aqueous ethanol. Author(s) Gao, Da-Ming; Kobayashi, Takashi; Adachi, Shuji Citation Food chemistry (2015), 175: 465-470 Issue Date 2015-05-15 URL http://hdl.handle.net/2433/193287 Right © 2014 Elsevier Ltd. Type Journal Article Textversion author Kyoto University Synthesis of rare sugars Production of rare sugars from common sugars in subcritical aqueous ethanol Da-Ming Gao, Takashi Kobayashi and Shuji Adachi* Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan Abstract A new isomerization reaction was developed to synthesize rare ketoses. D-Tagatose, D-xylulose, and D-ribulose were obtained in the maximum yields of 24%, 38%, and 40%, respectively, from the corresponding aldoses, D-galactose, D-xylose, and D-ribose, by treating the aldoses with 80% (v/v) subcritical aqueous ethanol at 180 °C. The maximum productivity of D-tagatose was ca. 80 g/(L·h). Increasing the concentration of ethanol significantly increased the isomerization of D-galactose. Variation in the reaction temperature did not significantly affect the production of D-tagatose from D-galactose. Subcritical aqueous ethanol converted both 2,3-threo and 2,3-erythro aldoses to the corresponding C-2 ketoses in high yields. Thus, the treatment of common aldoses in subcritical aqueous ethanol can be regarded as a new method to synthesize the corresponding rare sugars. Keywords: D-tagatose; D-xylulose; D-ribulose; ketose–aldose isomerization; subcritical aqueous ethanol 1.
    [Show full text]
  • Sucrose Metabolism and Exopolysaccharide Production by Lactobacillus Sanfranciscensis
    Lehrstuhl für Technische Mikrobiologie Sucrose metabolism and exopolysaccharide production by Lactobacillus sanfranciscensis Maher Korakli Vollständiger Abdruck der von der Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt der Technischen Universität München zur Erlangung des akademischen Grades eines Doktors der Naturwissenschaften genehmigten Dissertation. Vorsitzender: Univ.-Prof. Dr. rer. nat. habil. S. Scherer Prüfer der Dissertation: 1. Univ.-Prof. Dr. rer. nat. habil. R. F. Vogel 2. Univ.-Prof. Dr. rer. nat. W. P. Hammes, Univ. Hohenheim 3. Univ.-Prof. Dr.-Ing. Dr.-Ing. habil. W. Back Die Dissertation wurde am 29.10.2002 bei der Technischen Universität München eingereicht und durch die Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt am 9.12.2002 angenommen. Lehrstuhl für Technische Mikrobiologie Sucrose metabolism and exopolysaccharide production by Lactobacillus sanfranciscensis Maher Korakli Doctoral thesis Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt Freising 2002 Mein herzlicher Dank gilt: Meinem Doktorvater Prof. Rudi F. Vogel für die Überlassung des Themas, die zahlreichen Anregungen und die stete Bereitschaft zu fachlichen Diskussionen, für das mir entgegengebrachte Vertrauen und für den gewährten Raum meine Forschungsideen zu verwirklichen. Dr. Michael Gänzle für die motivierende und kritische Begleitung der Arbeit, die ständige Diskussionsbereitschaft und hilfreichen Anregungen. Monika Thalhammer, Nicole Kleber, Stephan Pröpsting, Melanie Pavlović, Konstanze Graser, Patrick Schwindt and allen fleißigen Händen für die fruchtbare Zusammenarbeit. Bedanken möchte ich mich weiterhin bei Angela Seppeur, Holger Schmidt, Georg Maier, Monika Hadek und Claudine Seeliger für die stete Hilfsbereitschaft. Darüber hinaus gilt mein Dank allen Mitarbeiterinnen und Mitarbeitern des Lehrstuhles für Technische Mikrobiologie für die kollegiale Zusammenarbeit und entspannte Laboratmosphäre. Contents 1.
    [Show full text]
  • Application of Natural, Non-Nutritive, High-Potency Sweeteners and Sugar
    APPLICATION OF NATURAL, NON-NUTRITIVE, HIGH-POTENCY SWEETENERS AND SUGAR ALCOHOLS INDIVIDUALLY AND IN COMBINATION IN AN ACIDIFIED PROTEIN BEVERAGE MODEL A Thesis presented to the Faculty of the Graduate School at the University of Missouri-Columbia In Partial Fulfillment of the Requirements for the Degree Master of Science by WEN ZHANG Dr. Ingolf Gruen, Thesis Supervisor MAY 2014 The undersigned, appointed by the dean of the Graduate School, have examined the thesis entitled APPLICATION OF NATURAL, NON-NUTRITIVE, HIGH-POTENCY SWEETENERS AND SUGAR ALCOHOLS INDIVIDUALLY AND IN COMBINATION IN AN ACIDIFIED PROTEIN BEVERAGE MODEL presented by Wen Zhang, a candidate for the degree of Master of Science, and hereby certify that, in their opinion, it is worthy of acceptance. Dr. Ingolf Gruen, Food Science Dr. Andrew Clarke, Food Science Dr. Heather Leidy, Nutrition & Exercise Physiology Dr. Koushik Adhikari, Department of Human Nutrition, Kansas State University ACKNOWLEDGEMENTS I would like to thank Dr. Ingolf Gruen for all his support and guidance throughout all of my academic endeavors. I could not ask for a better mentor. I accredit you for my interest in the field of sensory science and ingredients application. You are always open- minded to any conversation related to my research and career development. Your faith in me strengthens my desire and confidence not only on the project, but also on career matters. Although my time at the University of Missouri is finished, I will keep in touch with you, my best advisor, to have a long-term relationship in the future. To my committee members, Dr. Andrew Clarke, Dr.
    [Show full text]