DOCSLIB.ORG

Carbohydrates Hydrates of Carbon: General Formula Cn(H2O)N Plants

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Carbohydrates Hydrates of Carbon: General Formula Cn(H2O)N Plants Chapter 25: Carbohydrates hydrates of carbon: general formula Cn(H2O)n Plants: photosynthesis hν 6 CO2 + H2O C6H12O6 + 6 O2 Polymers: large molecules made up of repeating smaller units (monomer) Biopolymers: Monomer units: carbohydrates (chapter 25) monosaccharides peptides and proteins (chapter 26) amino acids nucleic acids (chapter 28) nucleotides 315 25.1 Classification of Carbohydrates: I. Number of carbohydrate units monosaccharides: one carbohydrate unit (simple carbohydrates) disaccharides: two carbohydrate units (complex carbohydrates) trisaccharides: three carbohydrate units polysaccharides: many carbohydrate units CHO H OH HO HO HO H HO HO O HO O glucose H OH HO HO OH HO H OH OH CH2OH HO HO HO O HO O HO HO O HO HO O HO HO HO O O O O O HO HO O HO HO HO O O HO HO HO galactose OH + glucose O glucose = lactose polymer = amylose or cellulose 316 160 II. Position of carbonyl group at C1, carbonyl is an aldehyde: aldose at any other carbon, carbonyl is a ketone: ketose III. Number of carbons three carbons: triose six carbons: hexose four carbons: tetrose seven carbons: heptose five carbons: pentose etc. IV. Cyclic form (chapter 25.5) CHO CHO CHO CHO CH2OH H OH HO H H OH H OH O CH2OH H OH H OH HO H HO H CH2OH H OH H OH H OH CH2OH H OH H OH CH OH 2 CH2OH glyceraldehyde threose ribose glucose fructose (triose) (tetrose) (pentose) (hexose) (hexose) 317 (aldohexose) (ketohexose) 25.2: Depicting carbohydrates stereochemistry: Fischer Projections: representation of a three-dimensional molecule as a flat structure. Tetrahedral carbon represented by two crossed lines: horizontal line is coming vertical line is going back out of the plane of the behind the plane of the page (toward you) paper (away from you) substituent carbon (R)-glyceraldehyde CHO CHO CHO H OH H OH H C CH2OH HO CH2OH CH2OH (S)-glyceraldehyde CHO CHO CHO HO H HO H HO C CH OH H 2 CH OH CH2OH 2 318 161 Manipulation of Fischer Projections 1. Fischer projections can be rotate by 180° only! CHO CH2OH CHO CH2OH 180 ° H OH HO H 180 ° HO H H OH CH2OH CHO CH2OH CHO (R) (R) (S) (S) 180° 180° Valid Valid Fischer Fischer projection projection 319 a 90° rotation inverts the stereochemistry and is illegal! 90 ° CHO OH H OH ! OHC CH2OH CH2OH H (R) (S) 90 ° This is not the correct convention 90° for Fischer projections Should be projecting toward you Should be projecting away you This is the correct convention for Fischer projections and is the enantiomer 320 162 2. If one group of a Fischer projection is held steady, the other three groups can be rotated clockwise or counterclockwise. hold steady CHO CHO H OH HO CH2OH CH2OH H (R) (R) CHO H HO H OHC OH hold steady CH2OH CH2OH (S) (S) 120° 120° hold hold steady steady hold steady 120° 120° hold hold 321 hold steady steady steady Assigning R and S Configuration to Fischer Projections 1. Assign priorities to the four substitutents according to the Cahn-Ingold-Prelog rules 2. Perform the two allowed manipulations of the Fischer projection to place the lowest priority group at the top (or bottom). 3. If the priority of the groups 1-2-3 are clockwise then assign the center as R, if 1-2-3 are counterclockwise then assign the center as S. 2 place at the top 4 CO2H H 1 H2N H 4 2 HO2C NH2 1 hold steady CH3 CH3 rotate other 3 3 three groups counterclockwise 1-2-3 counterclockwise = S 2 4 2 CO2H H CO2H 4 1 2 H NH2 1 H2N CO2H H2N CH3 CH3 1 3 CH3 H 3 3 4 1-2-3 clockwise = R 322 163 Fischer projections with more than one chiral center: 1 CHO CHO 2 HO H HO H 3 H OH H OH 4 CH2OH CH2OH Threose 2 CHO H 4 1 2 1 2 4 2 HO H OHC S OH 3 3 4 H OH 4 H OH 1 Hold Steady 1 3 CH2OH CH2OH 3 (2S, 3R) H 4 H 4 Hold Steady 2 1 2 1 2 S 2 OHC OH OHC OH 3 3 HO CH OH 4 H OH 1 1 2 R 3 H CH OH 2 4 3 323 25.3 D, L Sugars Glyceraldhyde- before the R/S convention, stereochemistry was related to (+)-glyceraldhyde CHO CHO H OH HO H CH2OH CH2OH D-glyceraldehyde L=glyceraldehyde R-(+)-glyceraldhyde (+)-rotation = dextrorotatory = D D-carbohydrate have the -OH group of the highest numbered chiral carbon pointing to the right in the Fisher projection as in R-(+)-glyceraldhyde CHO CHO CHO CHO H OH H OH HO H HO H HO H H OH HO H H OH H OH H OH HO H HO H H OH CH2OH CH2OH HO H CH2OH CH2OH D- glucose D-ribose L-ribose L- glucose Most carbohydrate in nature are of the D-series 324 164 For carbohydrates, the convention is to put the carbonyl group at the top for aldoses and closest to the top for ketoses. The carbons are numbered from top to bottom. 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 is pointing to the right in the Fischer projection, the sugar is designated as D (Dextro: Latin for on the right side). If the hydroxyl group is pointing to the left in the Fischer projection, 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 3 4 HO H H OH highest numbered highest numbered 5 HO 4 H stereogenic carbon H OH stereogenic carbon 5 CH2OH 6 CH2OH 325 D-Glucose L-Arabinose 24.4 Configuration of the Aldoses: triose tetroses CHO CHO CHO H OH HO H H OH H OH H OH CH2OH CH2OH CH2OH D-glyceraldehyde D-erythrose D-threose pentoses 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 hexoses 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 326 165 25.5 Cyclic structures of Monosaccharides: hemiacetal formation O H+ HO OR2 + R2OH R1 H R1 H hemiacetal O OH H H cyclic hemiacetal OH O 327 328 166 25.6: Monosaccharide anomers: mutarotation Anomers: the hemiacetal or hemiketal carbon (the carbonyl carbon of the open form) is a new chiral center and is referred to as the anomeric carbon (hemi-acetal carbon of the closed form) CH OH Trans 2 CH2OH Cis HO HO O O HO HO H OH HO HO OH H α-D-Glucopyranose (36%) β-D-Glucopyranose (64%) (α-anomer: C1-OH and (β-anomer: C1-OH and CH OH are cis) CH2OH are trans) 2 The hemiacetal forms of pyranoses adopts a chair conformation. The hydroxyl of the new anomeric (acetal)carbon can be axial (α) or equatorial ( ). The anomers are diastereomers. β 329 The α- and β-anomers are in equilibrium. They interconvert through the open form. The pure anomers can be isolated by crystallization. When the pure anomers are dissolved in water they undergo mutarotation, the process by which they return to an equilibrium mixture of the anomers HO HO OH HO HO O O HO HO OH HO HO H CHO H H OH HO H β-anomer H OH H OH CH OH 2 HO HO OH HO HO O HO H HO H HO HO O OH α-anomer 330 167 25.7: Reactions of monosaccharides reacts like a carbonyl CHO H OH HO HO H HO reacts like HO O reacts like alcohols alcohols H OH HO H OH OH CH2OH Ester formation: H3C O O O O HO H C O CH O HO 3 3 H3C O O HO OH O O HO O CH3 pyridine H3C O O O !-D-glucopyranose O CH3 Ether Formation HO Ag O, CH I H3CO HO 2 3 O H3CO HO OH H CO O HO 3 OCH3 H3CO !-D-glucopyranose 331 Glycoside Formation HO OR + R O OR O H+ 2 H 2 2 + R2OH R1 H R1 H R1 H R2OH hemiacetal acetal O OH OR2 H H+ H H O O OH R2OH cyclic hemiacetal glycoside OH OH CH OH, HCl OH HO 3 O HO HO O + HO OH HO HO O HO OCH3 HO HO OCH3 methyl !-D-glucopyranoside methyl "-D-glucopyranoside When R2OH is another carbohydrate unit, complex carbohydrate are formed. 332 168 The Koenigs-Knorr Reaction AcO AcO AcO HBr ROH, Ag O AcO 2 O AcO AcO O AcO OAc O AcO AcO AcO OR AcO AcO Br Neighboring group participation directs the stereochemistry of the glycosidation reaction 333 Reduction of Monosaccharides reacts like a carbonyl CHO CH2OH H OH HO H OH HO HO H NaBH4 HO O HO H H OH HO H OH H OH OH H OH CH2OH CH2OH alditol Oxidation of Monosaccharides: aldoses can be oxidized to aldonic acids with Ag(I) in NH3 (Tollin’s reagent), Cu(II) (Fehling’s or Benedict’s reagent) or Br2.
Load more

Recommended publications
  • Fructose and Sucrose Intake Increase Exogenous Carbohydrate Oxidation During Exercise
    nutrients Article Fructose and Sucrose Intake Increase Exogenous Carbohydrate Oxidation during Exercise Jorn Trommelen 1, Cas J. Fuchs 1, Milou Beelen 1, Kaatje Lenaerts 1, Asker E. Jeukendrup 2, Naomi M. Cermak 1 and Luc J. C. van Loon 1,* 1 NUTRIM School of Nutrition and Translational Research in Metabolism, Maastricht University Medical Centre, P.O. Box 616, 6200 MD Maastricht, The Netherlands; [email protected] (J.T.); [email protected] (C.J.F.); [email protected] (M.B.); [email protected] (K.L.); [email protected] (N.M.C.) 2 School of Sport, Exercise and Health Sciences, Loughborough University, Loughborough LE11 3TU, UK; [email protected] * Correspondence: [email protected]; Tel.: +31-43-388-1397 Received: 6 January 2017; Accepted: 16 February 2017; Published: 20 February 2017 Abstract: Peak exogenous carbohydrate oxidation rates typically reach ~1 g·min−1 during exercise when ample glucose or glucose polymers are ingested. Fructose co-ingestion has been shown to further increase exogenous carbohydrate oxidation rates. The purpose of this study was to assess the impact of fructose co-ingestion provided either as a monosaccharide or as part of the disaccharide sucrose on exogenous carbohydrate oxidation rates during prolonged exercise in trained cyclists. −1 −1 Ten trained male cyclists (VO2peak: 65 ± 2 mL·kg ·min ) cycled on four different occasions for −1 180 min at 50% Wmax during which they consumed a carbohydrate solution providing 1.8 g·min of glucose (GLU), 1.2 g·min−1 glucose + 0.6 g·min−1 fructose (GLU + FRU), 0.6 g·min−1 glucose + 1.2 g·min−1 sucrose (GLU + SUC), or water (WAT).
    [Show full text]
  • The No-Amylose Diet the Goal of This Diet Is to Avoid Foods That Contain Amylose and Glucose Which in Turn Cause a Rapid Rise in Blood Sugar When Ingested
    The No-Amylose Diet The goal of this diet is to avoid foods that contain amylose and glucose which in turn cause a rapid rise in blood sugar when ingested. This diet is based on the 00-2-3 rule and is an easy way for you to remember what should or should not be included in your diet each day. • 0 sugars (glucose or sucrose, including corn syrup) • 0 amylose • 2 servings of protein that total at least 6 to 8 ounces • 3 servings each of vegetables that grow above the ground and fruit (except bananas) per day. Easy-To-Make Adjustments This diet allows for sufficient quantities of food so that you won’t be hungry and can actually enjoy good-tasting, high-quality meals. It just involves adjusting some of our habits and thought patterns when it comes to food. For instance, you can still eat a hamburger, just not the bun. Why not try some melted cheese and a hearty slice of tomato on top instead? Soups can be a nutritious and filling meal or snack, but not when they are loaded with pasta, potatoes, or rice. Why not try some delicious black bean soup or maybe a homemade cream-based tomato soup without the added sugar so often found in canned varieties? Benefits of This Eating Plan And added benefit of this diet is that it is also a gluten-free diet. The avoidance of wheat, oats, rye, and barley is the same for both diets. If you have also been advised to be on a gluten-free diet, no adjustments need to be made in order for you to eat gluten-free.
    [Show full text]
  • Carbohydrate Food List
    Carbohydrate Food List 1. Breads, grains, and pasta Portion Size Carbs (g) Bread 1 slice 10-20 Cornbread 1 piece (deck of 30 cards) Cornmeal (Dry) 2 Tbsp 12 Cream of wheat, cooked with water ½ cup 15 Croutons ½ cup 12 Flour, all-purpose, dry 2 Tbsp 12 Oatmeal, cooked with water ½ cup 12-15 Pasta, cooked 1 cup 45 Pita bread 6” to 9” pita 30-45 Rice, cooked 1 cup 45 Tortilla corn 6” tortilla 12 Tortilla flour 6” tortilla 15 2. Nuts and Legumes Portion size Carbs (g) Beans (black, pinto, refried) and ½ cup 18-22 lentils, as prepared Hummus ½ cup 15-20 Nuts, mixed ½ cup 15 3. Starchy Vegetables Portion size Carbs (g) Corn on the cob 6” to 9” ear 20-30 Corn, cooked or canned ½ cup 15 Peas ½ cup 12 Potato, baked 1 medium (6 oz) 40 Adult Diabetes Education Program - 1 - Potato, mashed ½ cup 15-20 Sweet potato/yams 1 medium (5 oz) 25 Winter squash (butternut, acorn, 1 cup 15-30 hubbard), cooked 4. Milk and yogurts Portion size Carbs (g) Almond milk (plain, unsweetened) 1 cup <1 Cow’s milk (fat-free, 1%, 2%, whole) 1 cup 12 Soy milk (plain, unsweetened) 1 cup 3 Yogurt (plain) 1 cup 14 Yogurt, Greek (plain) 1 cup 10 5. Fruits Portion Size Carbs (g) Apple 1 medium 15-30 (tennis ball) Applesauce (unsweetened) ½ cup 15 Apricots, dried 7 pieces 15 Banana 6”-9” 30-45 Blackberries, blueberries 1 cup 20 Cherries 12 15 Dates, dried 5-6 dates 30 Fruit cocktail, canned (in own juice) ½ cup 15 Grapefruit ½ large 15 Grapes 15 15 Kiwi 1 small (egg) 15 Mango, cubed and frozen ½ cup 15 Melons, cantaloupe or honeydew 1 cup 15 Orange 1 medium 15 (tennis ball) Adult Diabetes Education Program Carbohydrates Food List - 2 - Peaches, canned (in own juice) ½ cup 15 Pear 6 oz 20 Pineapple (fresh) 1 cup, diced 20 Plum 1 plum 10 Prunes, dried 3 prunes 15 Raisins 2 Tbsp 15 Raspberries 1 cup 15 Strawberries 1 cup halves 12 Watermelon 1 cup diced 12 6.
    [Show full text]
  • Some Nutritional Properties of Starch and Dietary Fiber in Barley Genotypes Containing Different Levels of Amylose
    Some Nutritional Properties of Starch and Dietary Fiber in Barley Genotypes Containing Different Levels of Amylose 2 I. BJORCK,' A.-C. ELIASSON, A. DREWS,' M. GUDMUNDSSON, 2 and R. KARLSSON3 ABSTRACT Cereal Chem. 67(4):327-333 The nutritional properties of starch and dietary fiber (DF) were studied differences in rate of starch hydrolysis were seen between boiled barley in barley genotypes containing different amylose contents: Waxy Campana flours. In contrast, autoclaving produced a slower course of amylolysis (-8% amylose); Alva, Lina, and Glacier normal (normal varieties, 25-27% in Glacier high, despite complete gelatinization. This material also amylose); and Glacier high (-35% amylose). On an equivalent starch contained a somewhat higher level of retrograded enzyme-resistant starch, basis, all barley varieties showed a somewhat higher availability to a- 3% (starch basis). The content of soluble DF was lower in Alva and amylase than a wheat reference. Among the barley flours, starch in the Lina (4.8%) compared with 6.5% in the other genotypes (dwb). The waxy variety was most available to a-amylase when tested raw. With viscosity of suspensions of isolated DF (1.6%, w/v) correlated to the excess water (90% H2 0), the gelatinization was completed at about 80 C, proportion of soluble DF and was in decreasing order: Waxy > Glacier as measured with differential scanning calorimetry, irrespective of high > Alva. When added to a starch suspension, isolated barley DF amylose content. At lower moisture (50% H2 0), the temperature interval preparations were equally effective in reducing the rate of gastric emptying for gelatinization was considerably broadened.
    [Show full text]
  • Pharmaceutical Compositions of Rifaximin Pharmazeutische Rifaximin-Zusammensetzungen Compositions Pharmaceutiques De Rifaximine
    (19) TZZ Z__ T (11) EP 2 011 486 B2 (12) NEW EUROPEAN PATENT SPECIFICATION After opposition procedure (45) Date of publication and mention (51) Int Cl.: of the opposition decision: A61K 9/20 (2006.01) A61K 31/44 (2006.01) 12.08.2015 Bulletin 2015/33 (45) Mention of the grant of the patent: 23.05.2012 Bulletin 2012/21 (21) Application number: 08252198.0 (22) Date of filing: 26.06.2008 (54) Pharmaceutical compositions of rifaximin Pharmazeutische Rifaximin-Zusammensetzungen Compositions pharmaceutiques de rifaximine (84) Designated Contracting States: (56) References cited: AT BE BG CH CY CZ DE DK EE ES FI FR GB GR EP-A1- 0 616 808 EP-B1- 1 763 339 HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT WO-A-2006/094737 WO-A2-2006/039022 RO SE SI SK TR US-A- 6 140 355 US-A1- 2005 101 598 (30) Priority: 06.07.2007 IN KO09682007 • DUPONT ET AL: "Treatment of Travelers’ 23.06.2008 EP 08252158 Diarrhea: Randomized Trial Comparing Rifaximin, Rifaximin Plus Loperamide, and (43) Date of publication of application: Loperamide Alone" CLINICAL 07.01.2009 Bulletin 2009/02 GASTROENTEROLOGY AND HEPATOLOGY, AMERICAN GASTROENTEROLOGICAL (60) Divisional application: ASSOCIATION, US, vol. 5, no. 4, 17 April 2007 11176043.5 / 2 420 226 (2007-04-17), pages 451-456, XP022029177 ISSN: 14186563.4 / 2 837 378 1542-3565 • ARYA ET AL: "Rifaximin-the promising anti- (73) Proprietor: Lupin Ltd. microbial for enteric infections" JOURNAL OF Mumbai, Maharashtra 400 098 (IN) INFECTION, ACADEMIC PRESS, LONDON, GB, vol.
    [Show full text]
  • Biochemistry Entry of Fructose and Galactose
    Paper : 04 Metabolism of carbohydrates Module : 06 Entry of Fructose and Galactose Dr. Vijaya Khader Dr. MC Varadaraj Principal Investigator Dr.S.K.Khare,Professor IIT Delhi. Paper Coordinator Dr. Ramesh Kothari,Professor UGC-CAS Department of Biosciences Saurashtra University, Rajkot-5, Gujarat-INDIA Dr. S. P. Singh, Professor Content Reviewer UGC-CAS Department of Biosciences Saurashtra University, Rajkot-5, Gujarat-INDIA Dr. Charmy Kothari, Assistant Professor Content Writer Department of Biotechnology Christ College, Affiliated to Saurashtra University, Rajkot-5, Gujarat-INDIA 1 Metabolism of Carbohydrates Biochemistry Entry of Fructose and Galactose Description of Module Subject Name Biochemistry Paper Name 04 Metabolism of Carbohydrates Module Name/Title 06 Entry of Fructose and Galactose 2 Metabolism of Carbohydrates Biochemistry Entry of Fructose and Galactose METABOLISM OF FRUCTOSE Objectives 1. To study the major pathway of fructose metabolism 2. To study specialized pathways of fructose metabolism 3. To study metabolism of galactose 4. To study disorders of galactose metabolism 3 Metabolism of Carbohydrates Biochemistry Entry of Fructose and Galactose Introduction Sucrose disaccharide contains glucose and fructose as monomers. Sucrose can be utilized as a major source of energy. Sucrose includes sugar beets, sugar cane, sorghum, maple sugar pineapple, ripe fruits and honey Corn syrup is recognized as high fructose corn syrup which gives the impression that it is very rich in fructose content but the difference between the fructose content in sucrose and high fructose corn syrup is only 5-10%. HFCS is rich in fructose because the sucrose extracted from the corn syrup is treated with the enzyme that converts some glucose in fructose which makes it more sweet.
    [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]
  • United States Patent Office
    - 2,926,180 United States Patent Office Patented Feb. 23, 1960 2 cycloalkyl, etc. These substituents R and R' may also be substituted with various groupings such as carboxyl 2,926,180 groups, sulfo groups, halogen atoms, etc. Examples of CONDENSATION OF AROMATIC KETONES WITH compounds which are included within the scope of this CARBOHYDRATES AND RELATED MATER ALS 5 general formula are acetophenone, propiophenone, benzo Carl B. Linn, Riverside, Ill., assignor, by mesne assign phenone, acetomesitylene, phenylglyoxal, benzylaceto ments, to Universal Oil Products Company, Des phenone, dypnone, dibenzoylmethane, benzopinacolone, Plaines, Ill., a corporation of Delaware dimethylaminobenzophenone, acetonaphthalene, benzoyl No Drawing. Application June 18, 1957 naphthalene, acetonaphthacene, benzoylnaphthacene, ben 10 zil, benzilacetophenone, ortho-hydroxyacetophenone, para Serial No. 666,489 hydroxyacetophenone, ortho - hydroxy-para - methoxy 5 Claims. (C. 260-345.9) acetophenone, para-hydroxy-meta-methoxyacetophenone, zingerone, etc. This application is a continuation-in-part of my co Carbohydrates which are condensed with aromatic pending application Serial No. 401,068, filed December 5 ketones to form a compound selected from the group 29, 1953, now Patent No. 2,798,079. consisting of an acylaryl-desoxy-alditol and an acylaryl This invention relates to a process for interacting aro desoxy-ketitol include simple sugars, their desoxy- and matic ketones with carbohydrates and materials closely omega-carboxy derivatives, compound sugars or oligo related to carbohydrates. The process relates more par saccharides, and polysaccharides. ticularly to the condensation of simple sugars, their 20 Simple sugars include dioses, trioses, tetroses, pentoses, desoxy- and their omega-carboxy derivatives, compound hexoses, heptoses, octoses, nonoses, and decoses. Com sugars or oligosaccharides, and polysaccharides with aro pound sugars include disaccharides, trisaccharides, and matic ketones in the presence of a hydrogen fluoride tetrasaccharides.
    [Show full text]
  • Sia: the Sugar Code of Life
    Journal of General Surgery Open Access Full Text Article Research Article Sia: The Sugar Code of Life This article was published in the following Scient Open Access Journal: Journal of General Surgery Received November 05, 2017; Accepted November 27, 2017; Published December 04, 2017 Robert Skopec* Abstract Analyst-researcher, Dubnik, Slovakia, Europe Our cells are coated with sugar, and when it comes to cancer, that’s anything but sweet. In a recent talk at TEDxStanford, chemist Carolyn Bertozzi explained why. She studies sialic acid, a sugar that seems to deceive the immune system, allowing cancer cells to evade the body’s defenses. This work focuses on the complex, sugary structures surrounding human cells. That foliage-like coating, it turns out, can tell us a lot of our body – it even reveals a patient’s blood type. Sugar and carbohydrates are dangerous supporters of different types of cancer. Introduction As it can be seen from the information of the American Chemical Society (ACS), ideally, the immune system can figure out which cells are bad, attack them and protect the body from disease. In the case of cancer cells, though, a special sugary coating tricks the immune system into ignoring them. The sialic acid, a sugar that’s denser in cancer cells than in other cells. It seems deceive the immune system, allowing the cancer cells to evade the body’s defenses. Unnoticed and unchallenged, cancer cells are free to divideMonosaccharides and run wild inside - Sialic the acid/N-acetylneuraminicbody [1,2]. acid N-acetylneuraminic acid, also known as Sialic acid, is a key component of important amino sugars that mediate cellular communication.
    [Show full text]
  • 1. Nucleotides A. Pentose Sugars – 5-Carbon Sugar 1) Deoxyribose – in DNA 2) Ribose – in RNA B. Phosphate Group C. Nitroge
    1. Nucleotides a. Pentose sugars – 5-Carbon sugar 1) Deoxyribose – in DNA 2) Ribose – in RNA b. Phosphate group c. Nitrogenous bases 1) Purines a) Adenine b) Guanine 2) Pyrimidines a) Cytosine b) Thymine 2. Types of Nucleic Acids a. DNA 1) Locations 2) Functions b. RNA 1) Locations 2) Functions E. High Energy Biomolecules 1. Adenosine triphosphate a. Uses 1) Active transport 2) Movement 3) Biosynthesis reactions b. Regeneration 1) ADP + Pi + Energy → ATP 4. Classes of proteins a. Structural – ex. Collagen, keratin b. Transport – Hemoglobin, many β-globulins c. Contractile – Actin and Myosin of muscle tissue d. Regulatory - Hormones e. Immunologic - Antibodies f. Clotting – Thrombin and Fibrin g. Osmotic - Albumin h. Catalytic – Enzymes 1) Characteristics of enzymes • Proteins (most); ribonucleoproteins (few/ribozymes) • Act as organic catalysts • Lower the activation energy of reactions • Not changed by the reaction • Bind to their substrates o Lock-and-key model of enzyme activity o Induced-fit model • Highly specific • Named by adding -ase to substrate name; e.g., maltose/maltase • May require cofactors which may be: o Nonprotein metal ions such as copper, manganese, potassium, sodium o Small organic molecules known as coenzymes. The B vitamins like thiamine (B1) riboflavin (B2) and nicotinamide are precursors of coenzymes. • May require activation; e.g., pepsinogen pepsin in stomach chief cells 4. Factors Affecting Enzyme Action • pH o pepsin (stomach) @ pH = 2; trypsin (small int.) @ pH = 8 • Temperature o Denatured by high temp’s. • Enzyme inhibitors o Competitive inhibitors o Noncompetitive inhibitors • Effect of substrate concentration and reversible reactions and the Law of Mass D.
    [Show full text]
  • Monosaccharide Disaccharide Oligosaccharide Polysaccharide Monosaccharide
    Carbohydrates Classification of Carbohydrates monosaccharide disaccharide oligosaccharide polysaccharide Monosaccharide is not cleaved to a simpler carbohydrate on hydrolysis glucose, for example, is a monosaccharide Disaccharide is cleaved to two monosaccharides on hydrolysis these two monosaccharides may be the same or different C12H22O11 + H2O C6H12O6 + C6H12O6 glucose sucrose (a monosaccharide) fructose (a disaccharide) (a monosaccharide) Higher Saccharides oligosaccharide: gives two or more monosaccharide units on hydrolysis is homogeneous—all molecules of a particular oligosaccharide are the same, including chain length polysaccharide: yields "many" monosaccharide units on hydrolysis mixtures of the same polysaccharide differing only in chain length Some Classes of Carbohydrates No. of carbons Aldose Ketose 4 Aldotetrose Ketotetrose 5 Aldopentose Ketopentose 6 Aldohexose Ketopentose 7 Aldoheptose Ketoheptose 8 Aldooctose Ketooctose Fischer Projections and D-L Notation Fischer Projections Fischer Projections Fischer Projections of Enantiomers Enantiomers of Glyceraldehyde CH O CH O H OH HO H D L CH2OH CH2OH (+)-Glyceraldehyde (–)-Glyceraldehyde The Aldotetroses An Aldotetrose 1 CH O 2 H OH 3 H OH D 4 CH2OH stereochemistry assigned on basis of whether configuration of highest-numbered stereogenic center is analogous to D or L-glyceraldehyde An Aldotetrose 1 CH O 2 H OH 3 H OH 4 CH2OH D-Erythrose The Four Aldotetroses CH O CH O H OH HO H D-Erythrose and L-erythrose are H OH HO H enantiomers CH2OH CH2OH D-Erythrose L-Erythrose The Four
    [Show full text]
  • Hydrocolloids Structure and Properties the Building Blocks for Structure Timothy J
    Hydrocolloids Structure and Properties The building blocks for structure Timothy J. Foster 18 month Meeting, Unilever Vlaardingen, March 29‐31, 2010 Manufactured Materials Foams Emulsions Natural Materials This shows a layer of onion (Allium) cells. Targeting Hydrocolloids For Specific Applications: Approach Material Ingredient Properties Microstructure Oral Process Response Packaging Distribution Storage Process Controlled oral response Process (mouth/gut) Controlling Structure (taste, flavour, texture) CONSTRUCTION DECONSTRUCTION Designed texture/ Ingredient In body functionality Ingredient appearance/ (enzymes) behaviour Interaction with body mucins Reconstruction (associative and new phase separation) Microstructure changes as a Impact on / of starting function of enzyme action materials / structures Re-assembly of structures as a function of digestion breakdown products and body secretions (micelle formation, delivery vehicles) Single Biopolymer systems Hydrocolloid Structure/ Function Need: - define biopolymer primary structure - understand the nature of the interaction / rates - understand the solvent effects - measure material properties - test influence of primary structure variation and changes in environmental conditions on mechanical properties. Hydrocolloid Materials & Function Gelling Thickening Emulsification Pectin Pectin • Gelatin Alginate Alginate • Milk proteins Starch Starch • Egg proteins Agar LBG Carrageenan • Soya proteins Guar gum Gellan • Pea proteins Gelatin Xanthan • Gum Arabic Milk proteins Egg proteins Hydrocolloid
    [Show full text]