United States Patent 1191 [11] Patent Number: 5,071,976 Stirling [45] Date of Patent: Dec

Total Page:16

File Type:pdf, Size:1020Kb

United States Patent 1191 [11] Patent Number: 5,071,976 Stirling [45] Date of Patent: Dec United States Patent 1191 [11] Patent Number: 5,071,976 Stirling [45] Date of Patent: Dec. 10, 1991 [ 54 1 No VEL H ETEROPOLYSACCHARIDE FOREIGN PATENT DOCUMENTS Inventor: David I. Stirling, Fanwood, 1589865 5/1981 United Kingdom _ [73] Assignee: Celgene Corporation, Warren, NJ. OTHER PUBLICATIONS [211 App}_ NOJ 270,404 Huq et al., Aust. J. BioL, 1978, vol. 31, pp. 311-316. Bergey’s Manual, 8th ed., 1979, Williams & Wilkins (p. [22] Filed: Nov. 7, 1988 268). Colby et al., Ann. Rev. Microbiol, 1979, vol. 33, pp. Related US. A lication Data 481-517 _ _ pp Byrom, D. in Microbial Growth on C1 Compounds, H. [63] Contmuauon o_f Ser. No. 820,535, Feb. 6, 1986, aban- Dalton ed.’ 1931’ pp. 278489. doned, wh1ch 1s a continuation of Ser. No. 700,564, Hackh’?’ 8 chemical Dictionary 4th Edition Feb. 11, 1985, abandoned. McGraw_Hin’ 1972. [51] Int. Cl.5 ..................... .. C08B 37/00; CllP 19/04; Prima'y Examiner__D_ w_ Robinson c1 1N 1/20 Assistant Examiner-Irene Marx [52] U5. Cl. .................................. .. 536/123; 435/ 101; Attorney, Agent, or Fl‘rm_-Mathews’ WOOdbI-idge’ & 435/2511 Collins [58] Field of Search ........................... .. 435/101, 252.1; 536/123 [57] ABSTRACT _ This invention provides a fermentation process which [56] References C'ted involves aerobically cultivating a strain of Methyle U.S. PATENT DOCUMENTS philus viscogenes under growth conditions to produce an 3 346 463 10/1967 Goren ............................... .. 435/101 accumula‘ed quantity Ofa novel type of exopolysaccha' 3,932,218 1/1976 Finn et al. , 435/101 ride’ Such as hetempdysacchafide Poly 54 4,514,563 4/1985 Fujiyama .... .. .. 435/101 4,638,059 1/1987 Sutherland ........................ .. 536/121 3 Claims, 2 Drawing Sheets US. Patent Dec. 10, 1991 Sheet 1 of 2 5,071,976 #Em 80.9 nd US. Patent Dec. 10, 1991 Sheet 2 of 2 5,071,976 NaE :bmm.NEE.595 Q 00 ON adntmmmEhm<mIw 5,071,976 1 2 methanol substrate to an accumulated quantity of an NOVEL HETEROPOLYSACCHARIDE exopolysaccharide. It is another object of this invention to provide a CROSS-REFERENCE TO RELATED novel facultative methylotroph species. APPLICATIONS It is another object of this invention to provide me This is a continuation of Ser. No. 06/826,535, ?led thylotrophic microorganism strains having the identify ing characteristics of strain ATCC 39893 . Feb. 6, 1986 which is in turn a continuation-in-part of It is a further object of this invention to provide a Ser. No. 06/700,564, ?led Feb. 11, 1985, both now aban novel heteropolysaccharide which exhibits properties doned. suitable for imparting pseudoplastic and thixotropic BACKGROUND OF THE INVENTION properties to aqueous solutions. Other objects and advantages of the present invention In the last decade the production of single-cell pro shall become apparent from the accompanying descrip tein(SCP) from Cycompounds has been studied exten tion and examples. sively both by academic and industrial laboratories. 5 Enterprises such as Mitsubishi Gas Chemical Co., Ho DESCRIPTION OF THE INVENTION echst, and I.C.I. have implemented pilot plantstudies, One or more objects of the present invention are but to date only I.C.I. is operating a full scale SCP accomplished by the provision of novel strains of bac plant. “Pruteen” is the registered trademark of the I.C.I. teria having identifying characteristics comprising: product and is made by the fermentation of the obligate 20 (a) aerobic, gram-negative, rod-shaped, motile and po methylotrophic bacterium, Methylophilus methylotro larly ?agellated cells; phus, which is eventually separated and dried to a pow (b) methylotroph capable of assimilating methanol via der or granules Methylophilus methylotrophus is an obli the ribulose monophosphate pathway; gate methylotroph which uses the ribulose monophos (0) capable of growth on fructose; and phate pathway(RMP) cycle of formaldehyde ?xation. 25 (d) optimal growth rate at a cultivation medium temper Methylophilus methylotrophus kStrain AS~1 is a gram ature of 30°43“ C. negative, nonpigmented rod with a single polar ?agel Generally the novel bacterial strains of the present lum. invention exhibit glucose dehydrogenase activity. In SCP production, methanol feedstock constitutes In another embodiment this invention provides a the highest percentage of the operating costs, so that 30 bacterial culture having the identifying characteristics any increase in the microbial growth rate yield has a of strain ATCC 39893, said culture being capable of direct in?uence on the operating costs of the SCP pro aerobic bioconversion of methanol to an extracellular duction. For this reason I.C.I. has applied recombinant accumulation of heteropolysaccharide. DNA technology to increase the cell yield by altering Subcultures of accession Number ATCC 39893 strain the genome of the Methylophilus methylotrophus micro can be obtained upon request from the permanent mi organism. The genes for the more ef?cient glutamate croorganism collection of the American Type Culture dehydrogenase nitrogen assimilation system-from Esch Collection, 12301 Parklawn Drive, Rockville, Md. erichia coli were cloned and inserted into a Methyle 20852. The microorganism deposition is in accordance philus methylotrophus strain. This strain previously had with the requirements of the Budapest Treaty for the its less efficient glutamate synthase nitrogen assimilation purpose of patent procedure. system blocked by means of DNA mutation, as de The bacterial strains having the identifying character scribed by J. Windass et in Nature, 287 396(1980). istics of strain ATCC 39893 are not members of any of Although methanol generally is viewed as a substrate the known methylotrophic species such as Methylo for the production of single cell protein, the factors that phi/us methylotrophus. For purposes of taxonomic iden qualify it for SCP manufacture also recommend metha ti?cation herein, the name Methylophilus viscogenes is assigned to the.. new facultative methylotroph species nol as a potential feedstock for the production of accu which includes bacterial strains having the identifying mulated extracellular metabolites such as exopolysac characteristics of strain ATCC 39893. charides. A number of microbial processes for the con The term “methylotroph” as empolyed herein refers version of methanol to value-added products have been to a microorgansim which is capable of growing non described but generally these are low-volume/high autotrophically on carbon compounds having one or priced compounds such as aminoacids. Thus, J. Bolbot more carbon atoms but no carbon-carbon bonds. “Au and C. Anthony in Proc. Soc. Gen. Microbial, 5, totrophic" refers to growth on a carbon dioxide sub 43(1978) found that a pyruvate dehydrogenase lacking strate. mutant of Pseudomonas AMI could accumulate the The term “facultative methylotroph" as employed aminoacids alanine and valine during growth on metha herein refers to a methylotroph which is capable of nol Y. Tani et al in Agric. Biol Chem, 42, 2275( 1978) growth on one or more heterotrophic substrates, e.g., have described the production of up to 5.2 grams per fructose. liter of L-serine from methanol employing an Arthrobac The term “Cl-compounds” as employed herein refers ter globlformi's strain. Up to the present time there has 60 to organic compounds which do not contain any car not been any report of methanol bioconversion to a bon-carbon bonds, such as methanol, formaldehyde, commodity type of bulk chemical. formate, forrnamide, carbon monoxide, dimethyl ether, Accordingly, it is an object of this invention to pro methylamine, dimethylamine, trimethylamine and tri vide a fermentation process for the bioconversion of a methylamine N-oxide. Cl-compound to an accumulated quantity of extracellu 65 The term “exopolysaccharide” as employed herein lar metabolite. refers to a polysaccharide which accumulates as an It is another object of this invention to provide a extracellular metabolite in a fermentation medium, as rapid growth culture medium for bio-oxidation of a exempli?ed by xanthan gum. 5,071,976 3 4 The term “heteropolysaccharide“ as employed facultative methylotroph which utilizes the ribulose herein refers to a polysaccharide which is composed of monophosphate pathway of C1 assimilation, and which at least two different kinds of monosaccharidic units, typically has a growth rate doubling time of 1-3 hours such as mannose and galactose. at 35°~40° C. The term “ribulose monophosphate pathway“ Strain ATCC 39893 grows on methanol, fructose and (RMP) as employed herein refers to the biochemical glucose. In addition, it will grow on a wider variety of cycle in which three molecules of formaldehyde are heterotropic substrates (e.g., succinate and pyruvate) condensed to produce either one molecule of pyruvate when an exogenous energy supply in the form of for or one molecule of dihydroxyacetone phosphate. mate or methanol is present. This is a property not Biochemical literature relating to elucidation of the previously described for any known microorganism. ribulose monophosphate pathway and its variations For purposes of identi?cation, bacteria manifesting this include Biochem. J., 144, 465(1974) by J. Strom et al; phenomenon are herein termed “latent facultative me Sci. Prog., 62, 167 (1975) by C. Anthony; and Biochem. thylotrophs”. J., 148, 513(1975) by Colby et al. Bacteria having the characteristics comprising those The ribulose monophosphate pathway involves en of strain ATCC 39893 are further identi?ed by non zymes which include G-phosphogluconate dehydrase/— slimy growth of pale orange colonies on solid media. phospho-Z-keto-3-digluconate aldolase; fructose di Another identifying characteristic of a strain ATCC phosphate aldolase; glucose-é-phosphate dehydro 39893 type of methylotrophic bacterium is a hexulose genase; 3-hexulose phosphate synthase; phosphofructo phosphate synthase/hexulose phosphate isomerase ac kinase; phosphoglucoisomerase; phospho-3-hexulose tivity (J. P. Van Dijken et al; FEMS. Microbiol. Lett., isomerase; phosphoriboisomerase; ribulose-S-phosphate 4, 97, 1978) of at least about 400 nanomoles of NADH 3-epimerase; transaldolasei transketolase; sedoheptulose formed per minute per milligram of protein.
Recommended publications
  • Postulated Physiological Roles of the Seven-Carbon Sugars, Mannoheptulose, and Perseitol in Avocado
    J. AMER. SOC. HORT. SCI. 127(1):108–114. 2002. Postulated Physiological Roles of the Seven-carbon Sugars, Mannoheptulose, and Perseitol in Avocado Xuan Liu,1 James Sievert, Mary Lu Arpaia, and Monica A. Madore2 Department of Botany and Plant Sciences, University of California, Riverside, CA 92521 ADDITIONAL INDEX WORDS. ‘Hass’ avocado on ‘Duke 7’ rootstock, phloem transport, ripening, Lauraceae ABSTRACT. Avocado (Persea americana Mill.) tissues contain high levels of the seven-carbon (C7) ketosugar mannoheptulose and its polyol form, perseitol. Radiolabeling of intact leaves of ‘Hass’ avocado on ‘Duke 7’ rootstock indicated that both perseitol and mannoheptulose are not only primary products of photosynthetic CO2 fixation but are also exported in the phloem. In cell-free extracts from mature source leaves, formation of the C7 backbone occurred by condensation of a three-carbon metabolite (dihydroxyacetone-P) with a four-carbon metabolite (erythrose-4-P) to form sedoheptulose-1,7- bis-P, followed by isomerization to a phosphorylated D-mannoheptulose derivative. A transketolase reaction was also observed which converted five-carbon metabolites (ribose-5-P and xylulose-5-P) to form the C7 metabolite, sedoheptu- lose-7-P, but this compound was not metabolized further to mannoheptulose. This suggests that C7 sugars are formed from the Calvin Cycle, not oxidative pentose phosphate pathway, reactions in avocado leaves. In avocado fruit, C7 sugars were present in substantial quantities and the normal ripening processes (fruit softening, ethylene production, and climacteric respiration rise), which occurs several days after the fruit is picked, did not occur until levels of C7 sugars dropped below an apparent threshold concentration of ≈20 mg·g–1 fresh weight.
    [Show full text]
  • Lecture 7 - the Calvin Cycle and the Pentose Phosphate Pathway
    Lecture 7 - The Calvin Cycle and the Pentose Phosphate Pathway Chem 454: Regulatory Mechanisms in Biochemistry University of Wisconsin-Eau Claire 1 Introduction The Calvin cycle Text The dark reactions of photosynthesis in green plants Reduces carbon from CO2 to hexose (C6H12O6) Requires ATP for free energy and NADPH as a reducing agent. 2 2 Introduction NADH versus Text NADPH 3 3 Introduction The Pentose Phosphate Pathway Used in all organisms Glucose is oxidized and decarboxylated to produce reduced NADPH Used for the synthesis and degradation of pentoses Shares reactions with the Calvin cycle 4 4 1. The Calvin Cycle Source of carbon is CO2 Text Takes place in the stroma of the chloroplasts Comprises three stages Fixation of CO2 by ribulose 1,5-bisphosphate to form two 3-phosphoglycerate molecules Reduction of 3-phosphoglycerate to produce hexose sugars Regeneration of ribulose 1,5-bisphosphate 5 5 1. Calvin Cycle Three stages 6 6 1.1 Stage I: Fixation Incorporation of CO2 into 3-phosphoglycerate 7 7 1.1 Stage I: Fixation Rubisco: Ribulose 1,5- bisphosphate carboxylase/ oxygenase 8 8 1.1 Stage I: Fixation Active site contains a divalent metal ion 9 9 1.2 Rubisco Oxygenase Activity Rubisco also catalyzes a wasteful oxygenase reaction: 10 10 1.3 State II: Formation of Hexoses Reactions similar to those of gluconeogenesis But they take place in the chloroplasts And use NADPH instead of NADH 11 11 1.3 State III: Regeneration of Ribulose 1,5-Bisphosphosphate Involves a sequence of transketolase and aldolase reactions. 12 12 1.3 State III:
    [Show full text]
  • Conversion of D-Ribulose 5-Phosphate to D-Xylulose 5-Phosphate: New Insights from Structural and Biochemical Studies on Human RPE
    The FASEB Journal • Research Communication Conversion of D-ribulose 5-phosphate to D-xylulose 5-phosphate: new insights from structural and biochemical studies on human RPE Wenguang Liang,*,†,1 Songying Ouyang,*,1 Neil Shaw,* Andrzej Joachimiak,‡ Rongguang Zhang,* and Zhi-Jie Liu*,2 *National Laboratory of Biomacromolecules, Institute of Biophysics, Chinese Academy of Sciences, Beijing, China; †Graduate University of Chinese Academy of Sciences, Beijing, China; and ‡Structural Biology Center, Argonne National Laboratory, Argonne, Illinois, USA ABSTRACT The pentose phosphate pathway (PPP) such as erythrose 4-phosphate, glyceraldehyde 3-phos- confers protection against oxidative stress by supplying phate, and fructose 6-phosphate that are necessary for NADPH necessary for the regeneration of glutathione, the synthesis of aromatic amino acids and production which detoxifies H2O2 into H2O and O2. RPE functions of energy (Fig. 1) (3, 4). In addition, a majority of the in the PPP, catalyzing the reversible conversion of NADPH used by the human body for biosynthetic D-ribulose 5-phosphate to D-xylulose 5-phosphate and is purposes is supplied by the PPP (5). Interestingly, RPE an important enzyme for cellular response against has been shown to protect cells from oxidative stress via oxidative stress. Here, using structural, biochemical, its participation in PPP for the production of NADPH and functional studies, we show that human D-ribulose (6–8). The protection against reactive oxygen species is ؉ 5-phosphate 3-epimerase (hRPE) uses Fe2 for cataly- exerted by NADPH’s ability to reduce glutathione, sis. Structures of the binary complexes of hRPE with which detoxifies H2O2 into H2O (Fig. 1).
    [Show full text]
  • Carbohydrates: Structure and Function
    CARBOHYDRATES: STRUCTURE AND FUNCTION Color index: . Very important . Extra Information. “ STOP SAYING I WISH, START SAYING I WILL” 435 Biochemistry Team *هذا العمل ﻻ يغني عن المصدر المذاكرة الرئيسي • The structure of carbohydrates of physiological significance. • The main role of carbohydrates in providing and storing of energy. • The structure and function of glycosaminoglycans. OBJECTIVES: 435 Biochemistry Team extra information that might help you 1-synovial fluid: - It is a viscous, non-Newtonian fluid found in the cavities of synovial joints. - the principal role of synovial fluid is to reduce friction between the articular cartilage of synovial joints during movement O 2- aldehyde = terminal carbonyl group (RCHO) R H 3- ketone = carbonyl group within (inside) the compound (RCOR’) 435 Biochemistry Team the most abundant organic molecules in nature (CH2O)n Carbohydrates Formula *hydrate of carbon* Function 1-provides important part of energy Diseases caused by disorders of in diet . 2-Acts as the storage form of energy carbohydrate metabolism in the body 3-structural component of cell membrane. 1-Diabetesmellitus. 2-Galactosemia. 3-Glycogen storage disease. 4-Lactoseintolerance. 435 Biochemistry Team Classification of carbohydrates monosaccharides disaccharides oligosaccharides polysaccharides simple sugar Two monosaccharides 3-10 sugar units units more than 10 sugar units Joining of 2 monosaccharides No. of carbon atoms Type of carbonyl by O-glycosidic bond: they contain group they contain - Maltose (α-1, 4)= glucose + glucose -Sucrose (α-1,2)= glucose + fructose - Lactose (β-1,4)= glucose+ galactose Homopolysaccharides Heteropolysaccharides Ketone or aldehyde Homo= same type of sugars Hetero= different types Ketose aldose of sugars branched unBranched -Example: - Contains: - Contains: Examples: aldehyde group glycosaminoglycans ketone group.
    [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]
  • Sedoheptulose in Photosynthesis by Plants
    TWO-WEEK LOAN COPY This is a Library Circulating Copy which may be borrowed for two weeks. For a personal retention copy, call Tech. Info. Division, Ext. 5545 UCRW.268 Unclassified - Biology Distribution UNIVERSITY OF CALIFOmIA Radiation Laboratory Contract No. W-7405-eng-48 SEDOHEPT[JLOSE IN PHOTOSYNTHESIS BY PLANTS A. A. Benson, J. A. Bassham, and Me Calvin May 1, 1951 Berkeley, California A. A. Benson, 6. A, Bassham, and M, Calvin Radiation Laboratory and Department of Ohemistry University of Calif omia, Berkeley May 1, 1951 Although its function has not been ascertained, the general 1 occurrence of sedohep~ulose, D-altroheptuLose, in the succulent plants is well established. This sugar has not been identified in the majority of the members of the plat lringdom, but it now appears possibae that its phosphate esters may perform a vital function during photosynthesis. We haw isolated labeled sedoheptulose monopho sphate in cl% 2 photosynthesis products of all the plants thus far studied in this laboratory (~lorelh,Scenedesmus, Rhodospfr5.llyn rubn~,and the leaves of barley seedlings, soy bean, alf~lfa,sugar beet, spinach and geranium). It is invariably found as monophosphate esters. At least two such esters have been observed in radiograms of C1'-labeled Scenedesmus. The mjor one is associated with fructose monophosphztte while the minor one is inseparable, as yet, from glucose monophosphate. Sedoheptulose may be liberated e~zymticallyfrom its phosphates during the lrilling of the plan-i;,'but it has not been observed to accwnulate In amounts exceeding tbe steady state concentrations of -these phosphates. .--LL- * This work was sponsored bp the United States Atomic Energy Cormnission, -- This suggests its participation only as a phosphate in most plznts.
    [Show full text]
  • The Metabolic Building Blocks of a Minimal Cell Supplementary
    The metabolic building blocks of a minimal cell Mariana Reyes-Prieto, Rosario Gil, Mercè Llabrés, Pere Palmer and Andrés Moya Supplementary material. Table S1. List of enzymes and reactions modified from Gabaldon et. al. (2007). n.i.: non identified. E.C. Name Reaction Gil et. al. 2004 Glass et. al. 2006 number 2.7.1.69 phosphotransferase system glc + pep → g6p + pyr PTS MG041, 069, 429 5.3.1.9 glucose-6-phosphate isomerase g6p ↔ f6p PGI MG111 2.7.1.11 6-phosphofructokinase f6p + atp → fbp + adp PFK MG215 4.1.2.13 fructose-1,6-bisphosphate aldolase fbp ↔ gdp + dhp FBA MG023 5.3.1.1 triose-phosphate isomerase gdp ↔ dhp TPI MG431 glyceraldehyde-3-phosphate gdp + nad + p ↔ bpg + 1.2.1.12 GAP MG301 dehydrogenase nadh 2.7.2.3 phosphoglycerate kinase bpg + adp ↔ 3pg + atp PGK MG300 5.4.2.1 phosphoglycerate mutase 3pg ↔ 2pg GPM MG430 4.2.1.11 enolase 2pg ↔ pep ENO MG407 2.7.1.40 pyruvate kinase pep + adp → pyr + atp PYK MG216 1.1.1.27 lactate dehydrogenase pyr + nadh ↔ lac + nad LDH MG460 1.1.1.94 sn-glycerol-3-phosphate dehydrogenase dhp + nadh → g3p + nad GPS n.i. 2.3.1.15 sn-glycerol-3-phosphate acyltransferase g3p + pal → mag PLSb n.i. 2.3.1.51 1-acyl-sn-glycerol-3-phosphate mag + pal → dag PLSc MG212 acyltransferase 2.7.7.41 phosphatidate cytidyltransferase dag + ctp → cdp-dag + pp CDS MG437 cdp-dag + ser → pser + 2.7.8.8 phosphatidylserine synthase PSS n.i. cmp 4.1.1.65 phosphatidylserine decarboxylase pser → peta PSD n.i.
    [Show full text]
  • Ii- Carbohydrates of Biological Importance
    Carbohydrates of Biological Importance 9 II- CARBOHYDRATES OF BIOLOGICAL IMPORTANCE ILOs: By the end of the course, the student should be able to: 1. Define carbohydrates and list their classification. 2. Recognize the structure and functions of monosaccharides. 3. Identify the various chemical and physical properties that distinguish monosaccharides. 4. List the important monosaccharides and their derivatives and point out their importance. 5. List the important disaccharides, recognize their structure and mention their importance. 6. Define glycosides and mention biologically important examples. 7. State examples of homopolysaccharides and describe their structure and functions. 8. Classify glycosaminoglycans, mention their constituents and their biological importance. 9. Define proteoglycans and point out their functions. 10. Differentiate between glycoproteins and proteoglycans. CONTENTS: I. Chemical Nature of Carbohydrates II. Biomedical importance of Carbohydrates III. Monosaccharides - Classification - Forms of Isomerism of monosaccharides. - Importance of monosaccharides. - Monosaccharides derivatives. IV. Disaccharides - Reducing disaccharides. - Non- Reducing disaccharides V. Oligosaccarides. VI. Polysaccarides - Homopolysaccharides - Heteropolysaccharides - Carbohydrates of Biological Importance 10 CARBOHYDRATES OF BIOLOGICAL IMPORTANCE Chemical Nature of Carbohydrates Carbohydrates are polyhydroxyalcohols with an aldehyde or keto group. They are represented with general formulae Cn(H2O)n and hence called hydrates of carbons.
    [Show full text]
  • Monosaccharides
    UNIT 5 MONOSACCHARIDES Structure 5.1 Introduction 5.4 Biologically Important Sugar Derivatives Expected Learning Outcomes Sugar Acids 5.2 Overview of Carbohydrates Sugar Alcohols Amino Sugars 5.3 Monosaccharides Deoxy Sugars Linear Structure Sugar Esters Ring Structure Glycosides Conformations 5.5 Summary Stereoisomers 5.6 Terminal Questions Optical Properties 5.7 Answers 5.8 Further Readings 5.1 INTRODUCTION Carbohydrates constitute the most abundant organic molecules found in nature and are widely distributed in all living organisms. These are synthesized in nature by green plants, algae and some bacteria by photosynthesis. They also form major part of our diet and provide us energy required for the life sustaining activities such as growth, metabolism and reproduction. At microscopic level, these constitute the structural components of the cell such as cell membrane and cell wall. In this unit, we shall begin with general overview of the chemical nature of carbohydrates and their classification. The unit focuses mainly on the simplest carbohydrates known as monosaccharides. We shall learn about the chemical structures of different monosaccharides and how to draw them. We shall also discuss their stereochemistry in detail which would help to understand how change in orientation of same substituents results in different molecules with same chemical formula but different properties. We shall also discuss about some of the chemical reactions of monosaccharides resulting in 77 formation of important derivatives and their biological importance.
    [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]
  • 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]
  • Wo 2008/045259 A2
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date PCT (10) International Publication Number 17 April 2008 (17.04.2008) WO 2008/045259 A2 (51) International Patent Classification: (74) Agents: LEVINE, Edward, L. et al; Cargill, Incorpo A23L 1/00 (2006.01) A23L 1/0532 (2006.01) rated, 15407 McGinty Road West, MS 24, Wayzata, M in A23L 1/0524 (2006.01) nesota 55391 (US). (21) International Application Number: (81) Designated States (unless otherwise indicated, for every PCT/US2007/021245 kind of national protection available): AE, AG, AL, AM, AT,AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, (22) International Filing Date: 3 October 2007 (03.10.2007) CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, (25) Filing Language: English IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, (26) Publication Language: English PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, (30) Priority Data: ZM, ZW 11/544,989 6 October 2006 (06.10.2006) US (84) Designated States (unless otherwise indicated, for every (71) Applicant (for all designated States except US): kind of regional protection available): ARIPO (BW, GH, CARGILL, INCORPORATED [US/US]; 15407 GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, McGinty Road West, MS 24, Wayzata, Minnesota ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), 55391 (US).
    [Show full text]