DOCSLIB.ORG

Carbohydrates

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Carbohydrates LETS LEARN SOME GREEK!!!! The name glucose comes from the Greek word glykys (γλυκύς), meaning "sweet", plus the suffix "-ose" which denotes a sugar 4 chiral centers give 24 = the 16 stereoisomer s of hexose sugars. Chirality, or "handedness", Greek, (χειρ), kheir: "hand” chiral carbons are enantiomers Alpha α and Beta β are letters in the Greek alphabet σακχαρων Greek “sakcharon” = sugar Carbohydrates • Carbohydrates, or saccharides (saccharo is Greek for ―sugar) are polyhydroxy aldehydes or ketones, or substances that yield such compounds on hydrolysis. • Carbohydrates include not only sugar, but also the starches that we find in foods, such as bread, pasta, and rice. • The term ―carbohydrate comes from the observation that when you heat sugars, you get carbon and water (hence, hydrate of carbon). Carbohydrates and Biochemistry •Carbohydrates are compounds of tremendous biological importance: –they provide energy through oxidation –they supply carbon for the synthesis of cell components –they serve as a form of stored chemical energy –they form part of the structures of some cells and tissues •Carbohydrates, along with lipids, proteins, nucleic acids, and other compounds are known as biomolecules because they are closely associated with living organisms. Glucose (a monosaccharide) Plants: photosynthesis chlorophyll 6 CO2 + 6 H2O C6H12O6 + 6 O2 sunlight (+)-glucose (+)-glucose starch or cellulose respiration C H O + 6 O 6 CO + 6 H O + energy 6 12 6 2 2 2 Animals plant starch (+)-glucose (+)-glucose glycogen glycogen (+)-glucose (+)-glucose fats or aminoacids respiration (+)-glucose + 6 O2 6 CO2 + 6 H2O + energy CLASSIFICATION: 1- Monosaccharides (simple sugars): They can not be hydrolyzed into simpler units. E.g. glucose, galactose,ribose 2- Oligosaccharides (oligo = few): contain from two to ten monosaccharide units joined in glycosidic bonds. e.g. disaccharides (2 units) e.g. maltose and sucrose, trisaccharides (3 units).....etc. 3-Polysaccharides (poly = many): Also known as glycans. They are composed of more than ten monosaccharide units e.g. starch, glycogen, cellulose.....etc. MONOSACCHARIDES CLASSIFICATION OF MONOSACCHARIDES 1- According to the number of carbon atoms: .Trioses, contain 3 carbon atoms. Tetroses, contain 4 carbon atoms. Pentoses, contain 5 carbon atoms. Hexoses, contain 6 carbon atoms. Heptoses, contain 7 carbon atoms. Octoses. contain 8 carbon atoms. 2- According to the characteristic carbonyl group (aldehyde or ketone group): - Aldo sugars: aldoses: Contain aldehyde group e.g. glucose, ribose, erythrose and glyceraldehydes. - Keto sugars: ketoses: Contain ketone group e.g. fructose, ribulose and dihydroxy acetone. FORMS OF MONOSACCHARIDES: TRIOSES: D- glyceraldehyde Dihydroxyacetone TETROSES: Ketose CH2OH C = O H -C – OH CH2 OH D - erythrose D - erythrulose PENTOSES: HEXOSES: HEPTOSES: IS A KETOSE SUGAR D - sedoheptulose IT IS APTLY SAID THAT GLYCERALDEHYDE IS THE ‘REFERENCE CARBOHYDRATE’ Cyanohydrin Formation and Chain Extension. Kiliani-Fischer Synthesis- a series of reaction that extends carbon chain in a carbohydrate by one carbon and one chiral centre. 19 Determination of carbohydrate stereochemistry 1) HCN CHO CO2H 2) H2, Pd/BaSO4 HNO , H OH 3 H OH 3) H2O heat H OH H OH CH2OH CO2H D-(-)-erythrose tartaric acid CHO H OH Killiani-Fischer synthesis CH2OH D-(+)-glyceraldehyde CHO HNO , CO2H HO H 3 heat HO H H OH H OH 1) HCN CH2OH 2) H2, Pd/BaSO4 CO2H 3) H2O D-(-)-threose D-(-)-tartaric acid 20 1) HCN CHO CO2H 2) H2, Pd/BaSO4 3) H O H OH HNO3, H OH 2 heat H OH H OH H OH H OH CH OH 2 CO2H D-(-)-ribose ribonic acid CHO H OH Killiani-Fischer H OH synthesis CH2OH D-(-)-erythrose CHO CO2H HO H HNO3, HO H heat H OH H OH 1) HCN H OH H OH 2) H2, Pd/BaSO4 3) H2O CH2OH CO2H D-(-)-arabinose arabonic acid 21 1) HCN CHO CO2H 2) H , Pd/BaSO 2 4 H OH HNO3, H OH 3) H2O heat HO H HO H H OH H OH CH2OH CO2H D-(+)-xylose xylonic acid CHO HO H Killiani-Fischer H OH synthesis CH2OH D-(-)-threose CHO CO2H HO H HNO3, HO H heat HO H HO H 1) HCN H OH H OH 2) H2, Pd/BaSO4 3) H2O CH2OH CO2H D-(-)-lyxose lyxonic acid 22 CHO CHO CHO CHO H OH HO H H OH HO H H OH H OH HO H HO H H OH H OH H OH H OH CH2OH CH2OH CH2OH CH2OH D-ribose D-arabinose D-xylose D-lyxose CHO CHO CHO CHO CHO CHO CHO CHO H OH HO H H OH HO H H OH HO H H OH HO H H OH H OH HO H HO H H OH H OH HO H HO H H OH H OH H OH H OH HO H HO H HO H HO H H OH H OH H OH H OH H OH H OH H OH H OH CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH D-allose D-altrose D- glucose D-mannose D-gulose D-idose D-galactose D-talose CO2H CO2H CO2H CO2H CO2H CO2H CO2H CO2H H OH HO H H OH HO H H OH HO H H OH HO H H OH H OH HO H HO H H OH H OH HO H HO H H OH H OH H OH H OH HO H HO H HO H HO H H OH H OH H OH H OH H OH H OH H OH H OH CO2H CO2H CO2H CO2H CO2H CO2H CO2H CO2H optically optically optically optically optically optically optically optically inactive active active active active active inactive active enantiomers 23 PHYSICAL PROPERTIES OF MONOSACCHARIDES Most monosaccharides have a sweet taste (fructose is sweetest; 73% sweeter than sucrose). They are solids at room temperature. They are extremely soluble in water: Despite their high molecular weights, the presence of large numbers of OH groups make the monosaccharides much more water soluble than most molecules of similar MW. Glucose can dissolve in minute amounts of water to make a syrup (1 g / 1 ml H2O). Sugar Relative Sweetness Type Lactose 0.16 Disaccharide Galactose 0.22 Monosaccharide Maltose 0.32 Disaccharide Xylose 0.40 Monosaccharide Glucose 0.74 Monosaccharide Sucrose 1.00 Disaccharide Invert sugar1.30 Mixture of glucose and fructose Fructose 1.73 Monosaccharide ISOMERISM ENANTIOMER OPTICAL EPIMER ISOMER ANOMER ALDOSE-KETOSE ISOMER THE STEREOCHEMISTRY OF CARBOHYDRATES Two Forms of Glyceraldehyde •Glyceraldehyde, the simplest carbohydrate, exists in two isomeric forms that are mirror images of each other: 10 Stereoisomers • These forms are stereoisomers of each other. • Glyceraldehyde is a chiral molecule — it cannot be superimposed on its mirror image. The two mirror-image forms of glyceraldehyde are enantiomers of each other. Chirality and Handedness • Chiral molecules have the same relationship to each other that your left and right hands have when reflected in a mirror. 11 Chiral Carbons Chiral objects cannot be superimposed on their mirror images —e.g., hands, gloves, and shoes. Achiral objects can be superimposed on the mirror images —e.g., drinking glasses, spheres, and cubes. Any carbon atom which is connected to four different groups will be chiral, and will have two nonsuperimposable mirror images; it is a chiral carbon or a center of chirality. –If any of the two groups on the carbon are the same, the carbon atom cannot be chiral. Many organic compounds, including carbohydrates, contain more than one chiral carbon. Van’t Hoff’s 2n rule When a molecule has more than one chiral carbon, each carbon can possibly be arranged in either the right-hand or left-hand form, thus if there are n chiral carbons, there are 2n possible stereoisomers. Maximum number of possible stereoisomers = 2n Can you tell no. of possible stereoisomers of CHOLESTEROL? D and L isomers (Enantiomers) Enantiomers : They are the mirror image of each others. CHO CHO H - C– OH HO-C-H CH2OH CH2OH D-Glyceraldehyde L-Glyceraldehyde Carbohydrates are designated as D- or L- according to the stereochemistry of the highest numbered chiral carbon of the Fischer projection. If the hydroxyl group of the highest numbered chiral carbon is pointing to the right, the sugar is designated as D (Dextro: Latin for on the right side). If the hydroxyl group is pointing to the left, the sugar is designated as L (Levo: Latin for on the left side). Most naturally occurring carbohydrates are of the D-configuration. 1 CHO 1 H 2 OH CHO 3 2 HO H H OH 4 3 H OH HO H highest numbered highest numbered 5 HO 4 H "chiral" carbon H OH "chiral" carbon 5 CH2OH 6 CH2OH D-Glucose L-Arabinose CHO HO H CHO H OH HO H HO H H OH highest numbered highest numbered H OH "chiral" carbon HO H "chiral" carbon CH2OH CH2OH 33 L- glucose D-Arabinose What’s So Great About Chiral Molecules? Molecules which are enantiomers of each • other have exactly the same physical properties (melting point, boiling point, index of refraction, etc.) but not their interaction with polarized light. •Polarized light vibrates only in one plane; • it results from passing lights through polarizing filter Optical Activity A levorotatory(–) substance rotates polarized light to the left • [e.g., l-glucose; (-)-glucose]. •A dextrorotatory(+) substance rotates polarized light to the • right [e.g., d-glucose; (+)-glucose]. •Molecules which rotate the plane of polarized light are • optically active. •Many biologically important molecules are chiral and • optically active. Often, living systems contain only one of the possible stereochemical forms of a compound, or they are found in separate system. –D-lactic acid is found in living muscles; D-lactic acid is present in sour milk. • –In some cases, one form of a molecule is beneficial, and the enantiomer is a poison (e.g., • thalidomide).
Load more

Recommended publications
  • Liquid Chromatography with Electrospray Ionization And
    Hindawi Publishing Corporation International Journal of Analytical Chemistry Volume 2016, Article ID 9269357, 8 pages http://dx.doi.org/10.1155/2016/9269357 Research Article Liquid Chromatography with Electrospray Ionization and Tandem Mass Spectrometry Applied in the Quantitative Analysis of Chitin-Derived Glucosamine for a Rapid Estimation of Fungal Biomass in Soil Madelen A. Olofsson and Dan Bylund DepartmentofNaturalSciences,MidSwedenUniversity,85170Sundsvall,Sweden Correspondence should be addressed to Madelen A. Olofsson; [email protected] Received 2 September 2015; Accepted 12 January 2016 Academic Editor: Frantisek Foret Copyright © 2016 M. A. Olofsson and D. Bylund. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. This method employs liquid chromatography-tandem mass spectrometry to rapidly quantify chitin-derived glucosamine for estimating fungal biomass. Analyte retention was achieved using hydrophilic interaction liquid chromatography, with a zwitter- ionic stationary phase (ZIC-HILIC), and isocratic elution using 60% 5 mM ammonium formate buffer (pH 3.0) and 40% ACN. Inclusion of muramic acid and its chromatographic separation from glucosamine enabled calculation of the bacterial contribution to the latter. Galactosamine, an isobaric isomer to glucosamine, found in significant amounts in soil samples, was also investigated. Thetwoisomersformthesameprecursorandproductionsandcouldnotbechromatographicallyseparatedusingthisrapid method. Instead, glucosamine and galactosamine were distinguished mathematically, using the linear relationships describing the differences in product ion intensities for the two analytes. The m/z transitions of 180 → 72 and 180 → 84 were applied for the detection of glucosamine and galactosamine and that of 252 → 126 for muramic acid.
    [Show full text]
  • Chapter 12 Slides
    11/15/17 CHAPTER 12: Carbohydrates: Structure and Function OUTLINE • 12.1 Role of Carbohydrates • 12.2 Monosaccharides • 12.3 Complex Carbohydrates • 12.4 Carbohydrate Catabolism • 12.5 Oligosaccharides as Cell Markers CHAPTER 12: Carbohydrates: Structure and Function WHAT ARE CARBOHYDRATES? • Glucose and its derivatives are carbohydrates: Ø Carbohydrates are simple organic molecules that have a shared basic chemical Formula: Cn(H2O)n Ø The name “carbo + hydrate” represents that Fact that they are made from CO2 and H2O by photosynthesis • About halF oF all earth’s solid carbon is Found in two polymers of glucose found in plants: Ø Starch = major energy storage molecule Ø Cellulose = major structural component oF the plant cell wall (aka. “fiber”) CHAPTER 12: Carbohydrates: Structure and Function THE SIMPLEST CARBOHYDRATES • Monosaccharides are carbohydrates that cannot be hydrolyZed into simpler carbohydrates: Ø These are the Fundamental building blocks For all other carbohydrates (oFten called “simple sugars”) Ø All have Formulas of based on the basic pattern: Cn(H2O)n • Monosaccharides have speciFic Functional groups: 1. An aldehyde OR a ketone (not both!) 2. Several (two or more) alcohol (-OH) groups 1 11/15/17 CHAPTER 12: Carbohydrates: Structure and Function STRUCTURE & NOMENCLATURE OF MONOSACCHARIDES • Monosaccharides are classiFied by two features: 1. Length of their main carbon chain (utilize standard IUPAC naming For # oF carbons) 2. Whether they contain an aldehyde or ketone group • Names always end with –ose • Two common hexoses:
    [Show full text]
  • Amino Sugars and Muramic Acid—Biomarkers for Soil Microbial Community Structure Analysis
    Soil Biology & Biochemistry 36 (2004) 399–407 www.elsevier.com/locate/soilbio Amino sugars and muramic acid—biomarkers for soil microbial community structure analysis Bruno Glasera,*, Marı´a-Bele´n Turrio´nb, Kassem Alefc aInstitute of Soil Science and Soil Geography, University of Bayreuth, Bayreuth D-95440, Germany bArea of Soil Science and Soil Chemistry, ETSIIAA, University of Valladolid, Palencia 34004, Spain cUmwelt und Technologie Consulting, Bayreuth D-95448, Germany Received 13 December 2002; received in revised form 22 July 2003; accepted 7 October 2003 Abstract Characterizing functional and phylogenetic microbial community structure in soil is important for understanding the fate of microbially- derived compounds during the decomposition and turn-over of soil organic matter. This study was conducted to test whether amino sugars and muramic acid are suitable biomarkers to trace bacterial, fungal, and actinomycetal residues in soil. For this aim, we investigated the pattern, amounts, and dynamics of three amino sugars (glucosamine, mannosamine and galactosamine) and muramic acid in the total microbial biomass and selectively cultivated bacteria, fungi, and actinomycetes offive different soils amended with and without glucose. Our results revealed that total amino sugar and muramic acid concentrations in microbial biomass, extracted from soil after chloroform fumigation varied between 1 and 27 mg kg21 soil. In all soils investigated, glucose addition resulted in a 50–360% increase of these values. In reference to soil microbial biomass-C, the total amino sugar- and muramic acid-C concentrations ranged from 1–71 g C kg21 biomass-C. After an initial lag phase, the cultivated microbes revealed similar amino sugar concentrations of about 35, 27 and 17 g glucosamine-C kg21 TOC in bacteria, fungi, and actinomycetes, respectively.
    [Show full text]
  • Effect of Metal Chlorides on Glucose Mutarotation and Possible Implications on Humin Formation
    Reaction Chemistry & Engineering Effect of Metal Chlorides on Glucose Mutarotation and Possible Implications on Humin Formation Journal: Reaction Chemistry & Engineering Manuscript ID RE-COM-10-2018-000233.R1 Article Type: Communication Date Submitted by the 28-Nov-2018 Author: Complete List of Authors: Ramesh, Pranav; Rutgers The State University of New Jersey, Chemical and Biochemical Engineering Kritikos, Athanasios; Rutgers The State University of New Jersey, Chemical and Biochemical Engineering Tsilomelekis, George; Rutgers The State University of New Jersey, Chemical and Biochemical Engineering Page 1 of 5 ReactionPlease doChemistry not adjust & Engineering margins Journal Name COMMUNICATION Effect of Metal Chlorides on Glucose Mutarotation and Possible Implications on Humin Formation a a a Received 00th January 20xx, Pranav Ramesh , Athanasios Kritikos and George Tsilomelekis * Accepted 00th January 20xx DOI: 10.1039/x0xx00000x www.rsc.org/ An in-situ Raman spectroscopic kinetic study of the glucose suggested that the possible changes in the anomeric mutarotation reaction is presented herein. The effect of metal equilibrium especially via the stabilization of the α-anomer of chlorides on the ease of ring opening process is discussed. It is glucose, might be responsible for improved selectivity towards 7, 8 shown that SnCl4 facilitates the mutarotation process towards the fructose . This also agrees with the concept of anomeric β-anomer extremely fast, while CrCl3 appears to promote the specificity of enzymes; for instance, immobilized D-glucose formation of the α-anomer of glucose. Infrared spectra of humins isomerase has shown ~40% and ~110% higher conversion rates prepared in different Lewis acids underscore the posibility of starting with α–D-glucose as compared to equilibrated glucose multiple reaction pathways.
    [Show full text]
  • Supplementary Data
    Metabolomics in cancer research: Supplementary data 1 Supplementary Data 2 Supplementary methods 3 Additional information regarding the search strategy used in the main paper 4 Supplementary tables 5 Supplementary Table 1: List of reported metabolites to be altered in human cancers 6 Supplementary figures 7 Supplementary Figure 1: General overview over the metabolomics workflow 8 1 Metabolomics in cancer research: Supplementary data 9 Supplementary methods 10 Search strategy 11 The search strategy was described in the main paper. For the Web of Knowledge search an 12 additional refinement step was necessary to reduce irrelevant findings. The following research 13 areas of low relevance were excluded: 14 Plant Science, Biophysics, Agriculture, Environmental Sciences Ecology, Microbiology, 15 Computer Science, Mathematics, Cardiology, Engineering, Automation control Systems, 16 Marine Freshwater Biology, Behavioral Science, Physics, Developmental Biology, Zoology, 17 Psychiatry, Energy Fuels, Infectious Disease, Parasitology, Mycology, Rheumatology, 18 Psychology, Veterinary Sciences, Dentistry, Legal Medicine, Polymer Science, 19 Anesthesiology, Robotics, Sports Science, Forestry, Tropical Medicine, Virology, Water 20 Resources, Electrochemistry, Evolutionary Biology, Fisheries, Materials Science, 21 Oceanography, Substance Abuse, Geology, Nuclear Science Technology, Operations 22 Research Management, Orthopedics, Allergy, Biodiversity, Educational Research, 23 Metallurgy, Optics, Emergency Medicine, Geochemistry, History philosophy of science, 24 Mathematical methods in Social sciences, Mechanics, Social Issues, Thermodynamics 25 Additionally the abstracts had to contain one of the following keywords: 26 “MS” OR “mass spectrometry” OR “patients”. 2 Metabolomics in cancer research: Supplementary data 27 Supplementary tables 28 Supplementary Table 1: List of reported metabolites altered in human cancers. Metabolites in bold were reported from a study that validated 29 findings within an independent study population.
    [Show full text]
  • Structural Features
    1 Structural features As defined by the International Union of Pure and Applied Chemistry gly- cans are structures of multiple monosaccharides linked through glycosidic bonds. The terms sugar and saccharide are synonyms, depending on your preference for Arabic (“sukkar”) or Greek (“sakkēaron”). Saccharide is the root for monosaccha- rides (a single carbohydrate unit), oligosaccharides (3 to 20 units) and polysac- charides (large polymers of more than 20 units). Carbohydrates follow the basic formula (CH2O)N>2. Glycolaldehyde (CH2O)2 would be the simplest member of the family if molecules of two C-atoms were not excluded from the biochemical repertoire. Glycolaldehyde has been found in space in cosmic dust surrounding star-forming regions of the Milky Way galaxy. Glycolaldehyde is a precursor of several organic molecules. For example, reaction of glycolaldehyde with propenal, another interstellar molecule, yields ribose, a carbohydrate that is also the backbone of nucleic acids. Figure 1 – The Rho Ophiuchi star-forming region is shown in infrared light as captured by NASA’s Wide-field Infrared Explorer. Glycolaldehyde was identified in the gas surrounding the star-forming region IRAS 16293-2422, which is is the red object in the centre of the marked square. This star-forming region is 26’000 light-years away from Earth. Glycolaldehyde can react with propenal to form ribose. Image source: www.eso.org/public/images/eso1234a/ Beginning the count at three carbon atoms, glyceraldehyde and dihydroxy- acetone share the common chemical formula (CH2O)3 and represent the smallest carbohydrates. As their names imply, glyceraldehyde has an aldehyde group (at C1) and dihydoxyacetone a carbonyl group (at C2).
    [Show full text]
  • Xorox Univerelty Microfilms
    INFORMATION TO USERS This material was producad from a microfilm copy of the original document. While the moit advanced technological meant to photograph and reproduce thii document have been used, the quality it heavily dependent upon the quality of the original submitted. The following explanation of techniques is provided to help ou understand markings or patterns which may appear on this reproduction. 1. The sign or "target" for pages apparently lacking from the document photographed is "Missing Page(s)". If it was possible to ob tain the mining page(s) or section, they are spliced into the film along w ith: adjacent pages, This may have necessitated cutting thru an image and dupli eating adjacent pages to insure you complete continuity. 2. When an image on the film is obliterated with a large round black mark, it is an indication that the photographer suspected that the copy may have moved during exposure and thus cause a blurred image, fou will find a good image of the page in the adjacent frame. 3. When a map, drawing or chart, etc., was part of the material being photographed the photographer followed a definite method in "sectioning” the material. It is customary to begin photoi ig at the upper left hand comer of a large dieet and to continue photoi ig from left to right in equal sections with a small overlap. If necessary, sectioning is continued agein — beginning below the first row and continuing on until complete. 4. The majority of users indicate that the textual content is of greatest value, however, a somewhat higher quality reproduction could be made from "photographs" if essential to the understanding of the dissertation.
    [Show full text]
  • Analysis of Proteomic Responses of Freeze-Dried Oenococcus Oeni to Access the Molecular Mechanism of Acid Acclimation on Cell Freeze-Drying Resistance
    Accepted Manuscript Analysis of proteomic responses of freeze-dried Oenococcus oeni to access the molecular mechanism of acid acclimation on cell freeze-drying resistance Kun Yang, Yang Zhu, Yiman Qi, Tingjing Zhang, Miaomiao Liu, Jie Zhang, Xinyuan Wei, Mingtao Fan, Guoqiang Zhang PII: S0308-8146(19)30188-8 DOI: https://doi.org/10.1016/j.foodchem.2019.01.120 Reference: FOCH 24215 To appear in: Food Chemistry Received Date: 2 October 2018 Revised Date: 24 December 2018 Accepted Date: 17 January 2019 Please cite this article as: Yang, K., Zhu, Y., Qi, Y., Zhang, T., Liu, M., Zhang, J., Wei, X., Fan, M., Zhang, G., Analysis of proteomic responses of freeze-dried Oenococcus oeni to access the molecular mechanism of acid acclimation on cell freeze-drying resistance, Food Chemistry (2019), doi: https://doi.org/10.1016/j.foodchem. 2019.01.120 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Analysis of proteomic responses of freeze-dried Oenococcus oeni to access the molecular mechanism of acid acclimation on cell freeze-drying resistance Kun Yang1,2, Yang Zhu3, Yiman Qi2,Tingjing Zhang4, Miaomiao Liu2, Jie Zhang2, Xinyuan Wei2, Mingtao Fan2,*, Guoqiang Zhang1,* 1 College of Biological and Chemical Engineering, Anhui Polytechnic University, Wuhu, 241000, China 2 College of Food Science and Engineering, Northwest A ＆ F University, Yangling, 712100, China 3 School of Agriculture and Food Sciences, University of Queensland, QLD, 4046, Australia 4 College of Food Science and Technology, Henan University of Technology, Zhenzhou, 450001, China * Corresponding author: 1.
    [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]
  • NMR Spectroscopy and MD Simulations of Carbohydrates
    NMR spectroscopy and MD simul ations of carbohydrates Elin Säwén © Elin Säwén, Stockholm 2011 Cover picture: Five repeating units of the exopolysaccharide produced by Streptococcus thermophilus ST1 and a 1H NMR spectrum of the same exopolysaccharide. ISSN XXXX-XXXX ISBN XXX-XX-XXXXX-XX-X Printed in Sweden by US-AB, Stockholm 2011 Distributor: Department of Organic Chemistry, Stockholm University Till Ingrid Abstract Knowledge about the structure, conformation and dynamics of carbohydrates is important in our understanding of the way carbohydrates function in bio- logical systems, for example in intermolecular signaling and recognition. This thesis is a summary of five papers studying these properties in carbohy- drate-containing molecules with NMR spectroscopy and molecular dynamics simulations. In paper I, the ring-conformations of the six-membered rings of two car- baiduronic analogs were investigated. These carbasugars could potentially be used as hydrolytically stable mimics of iduronic acid in drugs. The study 4 showed that the equilibrium is entirely shifted towards the C1 conformation. Paper II is an investigation of the conformational flexibility and dynamics of two (1 →6)-linked disaccharides related to an oligosaccharide epitope expressed on malignant tumor cells. In paper III, the conformational space of the glycosidic linkage of the di- saccharide α-D-Man p-(1 →2)-α-D-Man p-OMe, which is present in N- and O- linked glycoproteins, was studied. A maximum entropy analysis using dif- ferent priors as background information was used and four new Karplus 3 3 equations for JC,C and JC,H coupling constants, related to the glycosidic linkage, were presented.
    [Show full text]
  • Synthesis and Sorting of Proteoglycans
    Journal of Cell Science 113, 193-205 (2000) 193 Printed in Great Britain © The Company of Biologists Limited 2000 JCS0690 COMMENTARY Synthesis and sorting of proteoglycans Kristian Prydz1,* and Knut Tomas Dalen2 1Department of Biochemistry and 2Institute for Nutrition Research, University of Oslo, Norway *Author for correspondence (e-mail: [email protected]) Published on WWW 13 January 2000 SUMMARY Proteoglycans are widely expressed in animal cells. type, which is acquired by use of particular Ser-Gly sites in Interactions between negatively charged glycosaminoglycan the protein core, might therefore be important for post- chains and molecules such as growth factors are essential for synthesis sorting. This links regulation of glycosaminoglycan differentiation of cells during development and maintenance synthesis to the post-Golgi fate of proteoglycans. of tissue organisation. We propose that glycosaminoglycan chains play a role in targeting of proteoglycans to their proper cellular or extracellular location. The variability seen Key words: Proteoglycan, Glycosaminoglycan, Sorting, Polarised in glycosaminoglycan chain structure from cell type to cell cell, Epithelial cell, Glycan INTRODUCTION VARIATION IN PROTEOGLYCAN COMPOSITION Proteoglycans (PGs) consist of a protein portion and long, PGs were initially grouped together because of the high unbranched polysaccharides (glycosaminoglycans or GAGs). negative charges of their GAG chains, which make separation The latter have a high negative charge, owing to the presence from other molecules by ion-exchange chromatography easy. of acidic sugar residues and/or modification by sulphate PGs are, however, not that similar. The core protein size ranges groups. The acidic sugar alternates with an amino sugar in from 10 kDa to >500 kDa, and the number of GAG chains repeated disaccharide units.
    [Show full text]
  • Mutarotation
    13 Mutarotation The α and β anomers are diastereomers of each other and usually have different specific rotations. A solution or liquid sample of a pure α anomer will rotate plane polarised light by a different amount and/or in the opposite direction than the pure β anomer of that compound. The optical rotation of the solution depends on the optical rotation of each anomer and their ratio in the solution. For example, if a solution of β-D-glucopyranose is dissolved in water, its specific optical rotation will be +18.7°. Over time, some of the β-D-glucopyranose will undergo mutarotation to become α-D-glucopyranose, which has an optical rotation of +112.2°. Thus the rotation of the solution will increase from +18.7° to an equilibrium value of +52.7° as some of the β form is converted to the α form. The equilibrium mixture is actually about 64% of β-D-glucopyranose and about 36% of α-D-glucopyranose, though there are also traces of the other forms including furanoses and open chained form. The α anomer is the major conformer, although somewhat controversially; this is due to the anomeric effect with the stabilization energy provided by n–σ* hyperconjugation. The observed rotation of the sample is the weighted sum of the optical rotation of each anomer weighted by the amount of that anomer present. 14 Therefore, one can use a polarimeter to measure the rotation of a sample and then calculate the ratio of the two anomers present from the enantiomeric excess, as long as one knows the rotation of each pure anomer.
    [Show full text]