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A World of Sugars: from Sugars in Space to Daily Life

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A World of Sugars: from Sugars in Space to Daily Life 11/10/2016 A World of Sugars: From Sugars in Space to Daily Life Serge Perez, Firenze, Ottobre 2016 1 2 1 11/10/2016 Sucrose HOH H O HO HO H H OH H O HO O OH Disaccharide D‐glucopyranose OH D‐fructofuranose OH Sugar cane : was discovered in New Guinea, arrived to India around 600 BC and reached Persia when Sugar beat : identified by a German Darius invaded India. Upon invading Spain, Arabs Chemist, Andreas Marggraf en 1747; and brought sugar to Europe around 700 AD. brought to culture under Napoleon on the occasion of the british blockade. Etymology : sanskrit "SARKARA" (grain), translated as sukkar in arabic, saccharum in latin and zucchero in italian Production of 145 millions tons/year of a « molecularly » pure product ! What do we mean by « Sugars » ? Refer to a vast familly of molecules, which are homogeneous (Cx (H2O)y ) and diversified. Made up of Carbone, Hydrogen & Oxygen. They are referred to as « Carbohydrates », « Hydrates de carbone » « Kohlenhydrate » but also « Saccharides » and « Glycans » Oligosaccharides, Polysaccharides Glycoconjugates as in Glycopeptides, Glycoproteins, Glycolipids 2 11/10/2016 Molecular Diversity of Monosaccharides Carbon chain (3 à 10 Carbons) multiforms All Carbons are functionalized Coexistence of a Carbonyl group (aldehyde or ketone) with several (2 to 9) Hydroxyl groups : aldoses / ketoses Dual character Electrophile – Nucleophile H O CH2OH AldoseH OH Ketose O HO H HO H CH2OH CH2OH Sugar in Space (400 light‐years away to Earth) Glycoaldehyde (and its reduced alcohol variant –ehyleneglycol) have been identifed from the energy it emits as it changes its rotational energy level by absorbing and emitting in the millimeter wavelength. Ribose ARN ADN Jørgensen, J. K.; Favre, C.; Bisschop, S.; Bourke, T.; Dishoeck, E.; Schmalzl, M. (2012). Detection of the simplest sugar, glycolaldehyde, in a solar‐type protostar with ALMA (http://www.eso.org/public/archives/releases/science papers/eso1234/eso1234a.pdf) 6 3 11/10/2016 Making Ribose in Artificial Cometary Ice Recreating the conditions of the early solar system in lab, mimicking process that can occur in molecular clouds as well as in protoplanetary disks. H2O, CH3 OH and NH3 put in vaccum and cooled to 80°K (during 6 days) 7 Molecular Diversity of Monosaccharides Heteroatoms –Nitrogen, Sulphur – may introduce other functionalites and enrich the corresponding sub families: glycosylamines, thiosugars, glucosinolates … Oxydized forms: uloses, glycaric acids, glyconics, glycuronics … Reduced forms: deoxy‐sugars, itols … Unsaturated variants : enoses, glycals … 4 11/10/2016 Chirality & Stereochemistry CHO H OH HO H H OH H OH CH2OH 9 Historical Representation of Monosaccharides 10 5 11/10/2016 Equilibrium Chain ‐ Ring There exists an equilibrium (reversible or not) between the linear chains and the cyclic form. Its formation is favored under weak acidic or alkaline conditions). The more stable rings are (4C & 1 O) (furanose) and (5C & 1O) (pyranose). Ring locking generates a crucial supplementaty complexity: the anomeric carbon: with two configurations. either , or Mutarotation : Configurational Equilibrium Hydroxyl group at C5 reacts with the aldehyde group at C1 and creates an a additional asymmetric carbon atom with and configuration. 6 11/10/2016 HO H HO H HO H HO H O O O O H H H OH HO H HO OH H OH H OH H OH H OH HO OH HO H H OH H H D-ribose D-arabinose D-xylose D-lyxose Aldopentoses HOH HOH HOH HOH H O HO O H O HO O HO HO HO HO H OH H OH HO OH HO OH H OH H H H OH H H OH H OH H H H H H D-Allose D-Altrose D-Glucose D-Mannose HOOH HOOH HOOH HOOH H O HO O H O HO O H H H H H OH H OH HO OH HO OH H OH H H H OH H H OH H OH H H H H H Aldohexoses D-Gulose D-Idose D-Galactose D-Talose Evolution of the Depiction of Monosaccharides Fischer assigned the dextrorotatory glucose (via glucaric acid) the projection with the OH group at C5 pointing to the right. But the absolute configuration was established in 1951 (Bijvoet) by X‐ray crystallography 14 7 11/10/2016 Conformational Complexity The most common rings are furanaoid or pyranoid, with five and six members. Furanose ring structures occur in Envelope (E) and Twist (T) conformations. Six membered ring structures can occur in 2 chairs (C), 6 boat (B), 6 Skew (S) and 12 half‐chair (H) conformations. These conformations result in orientating in space the different functions of the monosaccharide, which have an impact on recognition and reactivity. D-Glucose L-Fucose L-iduronic Acid The Isomer Barrier Nucleotides Peptides Glycans 4 bases 20 amino acids > 150 (700) monosaccharides Linear Linear Lineare or branchéed 2 sites linkage 4 sites linkage 5 sites linkage With 2 stéreo-chemistr ( / ) Hexanucleotide Hexapeptide Hexasaccharide 46 = 4096 206 = 64 000 000 192 780 943 360 (with 10 monosaccharides) High Coding Capacity of Glycans 16 R. A. Laine, Glycobiology, 4, 759-767 (1994) P. H. Seeberger, ACS Chem Biol, 2, 685-691 (2007) 8 11/10/2016 The Isomer Barrier •Have a very high number of monomers (substitution…). • Have many different ways of connecting monomers. • Have branching points. •Are difficult to synthesise … and to crystallize. •Are not the direct product of a gene (≠ proteins). • Cannot be amplified by PCR ( ≠ Nucleic acids). 17 A New and Complex Alphabet BioInformatics: Difficulty to encode the structures 18 9 11/10/2016 Oligosaccharides & Polysaccharides Structural Complexity and Functional Diversity Oligo & Polysaccharides : Monosaccharide units linked by glycosidic linkage One of the most stable linkage among those occurring in bio(macro)molecules 10 11/10/2016 Degradation polysaccharide : hydrolysis perform by Glycosidase oligosaccharide : Glucosyl Hydrolase (GH) Release Energy OH OH OH OH O HO O O O HO O H O HO HO OH HO 2 HO OH HO OH OH OH OH OH Cellobiose Glucose Glucose OH O Glucosyl Transferase (GT) HO HO OH O O O P P O Base Requires Energy O O O O Nucléoside diphosphate HO OH Biosynthesis (construction ) oligosaccharide : Glycosyltransferase polysaccharide : Major Functions Played by Polysaccharides Energy Stores Structural support Solution properties of physiological fluids Plasticity Extra-cellular matrix build-up Blood clot 22 11 11/10/2016 Amylose : Linear chain of glucoses linked 1,4 Amylopectin Energy Storage Combination of amylose + branched linked Polymers of Glucose 1,6 glycosidic bonds Glycogen some similarity to amylopectin but different types of branches Starch: A Multiscale Nanomaterial (Super-helice) (blocklets) molecules‐9 lamellae ‐8 ‐7 ‐6 granule ‐5 10 10 10 growth rings 10 10 24 12 11/10/2016 Other Energy Storage Polysaccharides, (with linear structures more rare, found in plants and small animals galactans (in snails) ; 20-30 units fructane (plants) 20-30 units Helianthus tuberosus Jerusalem artichoke Topinambour Topinanbur (carciofo di Gerusalemme) Fructans : Two Types of Structures : Inulin Phlein types HOH Inulin : H O HO HO H H OH H HOH O Phlein H O HO HO OH HO H O H OH H O O OH HO OH O OHO OH HO O O O OH -2,1 linkage O OH OH OH OH OH OH OH O n n HO O OH -2,6 linkage Phlein biosynthesized by phlein sucrase. OH OH High correlation of the chain length of phlein with the stress resistance. 13 11/10/2016 Structural Polysaccharides: Highly diverse from micro‐organisms to « higher organisms ». Bring mechanical stability and protection to bacterial, plants and animals. Bacteria Plants Animals Cellulose: Major Structural Constituents in Plants,….. Cellulose: Linear chains of 1,4 linked Glucose 14 11/10/2016 Cellulose: Several Levels of Structural Organizations 29 Cellulose Biosynthesis 300‐1000Adapted Glucose from residues Brown per et minuteal., Plant (speed: Physiol.Biochem., 300 nm/min) (2000) 30 15 11/10/2016 Pectins 31 Algae Anionic polysaccharides ‐ Gel forming (hydrocolloïds) : Agar & Carrageenan, Alginates. Agar et Carrageenan distributed in the cell walls of red algea : galactans et Alginate, distributed widely in mannans . Made up Mannose a the cell walls of brown algea Sulfated galactose. OH HO O OH O O HO O HO HO O Linear polysaccharides with n Mannuronic & Guluronique Modifications and variable patterns of sulfatations 16 11/10/2016 Bacteria Peptidoglycan : 1 or several layers, murein, ac. teichoïc (Gram+) External membranes: lipopolysaccharides and lipoproteins Not shown Polysaccharidic capsule OH Peptidoglycan : OH * O murein (murus : mur) O O O O O * HO AcHN AcHN (NAc)Glucosamine - ac. muramique H CO2H CH3 Téïchoic acids (teichos = mur) (Gram+ only) O O P O O core O O P O O n Core : glycerol, ribitol, monosaccharides & disaccharides (Galactose & GalactosamineNAc) 17 11/10/2016 Lipopolysaccharides (Gram(‐)) Animals Glycosaminoglycans (GAGs) • Linear polysaccharides: Uronic acid and Hexosamines •High viscosity ; elasticity • Connective tissues, intercellular space (cartilages) 18 11/10/2016 Glycosaminoglycans GAGs : Oligosaccharides 4 to 10 monosaccharide units, usually as a result of the degradation or transformation of polysaccharides. ‐Dextrins FructoOligoSaccharides (FOS GalactoOligoSaccharides (GOS) Cyclodextrines 19 11/10/2016 Cyclodextrins : (, , ) Cyclic Oligomers of 1‐4 linked 6,7,8 Glucoses Encapsulation Enhance stability, solubility, controled relase, masking odor Applications: Pharmaceutical, Cosmetics, Food Analytical chemistry: separation Honey Oligosaccharides Honey Crystallization F as Fructose & Fat 20 11/10/2016 The Most Common Disaccharides Lactose (galactose – glucose) HOOH HOH H O D-glucose H H O HO O H OH HO H H H H OH H OH D-galactose Linkage -1,4 Human Milk Oligosaccharides ….. The Most Common Disaccharides Maltose (glucose-glucose) HOH H O HO HO H H OH HOH H H O O HO H D-glucose H OH H OH Linkage -1,4 D-glucose 21 11/10/2016 The Most Common Disaccharides Trehalose (glucose-glucose) Cryoprotection HOH HOH Medical Applications : H O O H Stabilization & Protection HO OH HO H H OH antibodies, enzymes, embryos, H OH OH H H O H help in transplantation D-glucose D-glucose …cosmetic Linkage Cryoprotection- Tardigrades The Most Common Disaccharides Sucrose (glucose‐fructose) HOH D-glucose H O HO HO H H OH OH D-fructose H O O HO Liaison -1,2 OH HO Sugar beat Sugar cane 22 11/10/2016 Sucrochemistry….
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