Chemistry 333 Principles of Biochemistry
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A Review of Physiological Effects of Soluble and Insoluble Dietary Fibers
ition & F tr oo u d N f S o c l i e a n n c r e u s o J Journal of Nutrition & Food Sciences Perry and Ying, J Nutr Food Sci 2016, 6:2 ISSN: 2155-9600 DOI: 10.4172/2155-9600.1000476 Review Article Open Access A Review of Physiological Effects of Soluble and Insoluble Dietary Fibers Perry JR and Ying W* College of Agriculture, Human, and Natural Sciences, 13500 John A Merritt, Tennessee State University, Nashville, TN, USA *Corresponding author: Ying W, College of Agriculture, Human, and Natural Sciences, 13500 John A Merritt, Tennessee State University, Nashville, TN, United States, Tel: 615-963-6006; E-mail: [email protected] Rec date: Feb 18, 2016; Acc date: Mar 03, 2016; Pub date: Mar 14, 2016 Copyright: © 2016 Perry JR, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Abstract This paper seeks to characterize the effects of Total Dietary Fibers (TDFs), Soluble Dietary Fibers (SDFs), and Insoluble Dietary Fibers (IDFs) with regard to the rates of digestion, enzymatic activity, the metabolic syndrome, diabetes and glucose absorption, glycemic index, and weight gain. This review intends to narrow pertinent data from the vast body of research, including both in vivo and in vitro experiments. SDF and IDF share a number of the theorized beneficial properties in the diet including weight loss, increased satiety, effects on inflammatory markers, and intestinal microbiota. -
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. -
Fructose and Mannose in Inborn Errors of Metabolism and Cancer
H OH metabolites OH Review Fructose and Mannose in Inborn Errors of Metabolism and Cancer Elizabeth L. Lieu †, Neil Kelekar †, Pratibha Bhalla † and Jiyeon Kim * Department of Biochemistry and Molecular Genetics, University of Illinois, Chicago, IL 60607, USA; [email protected] (E.L.L.); [email protected] (N.K.); [email protected] (P.B.) * Correspondence: [email protected] † These authors contributed equally to this work. Abstract: History suggests that tasteful properties of sugar have been domesticated as far back as 8000 BCE. With origins in New Guinea, the cultivation of sugar quickly spread over centuries of conquest and trade. The product, which quickly integrated into common foods and onto kitchen tables, is sucrose, which is made up of glucose and fructose dimers. While sugar is commonly associated with flavor, there is a myriad of biochemical properties that explain how sugars as biological molecules function in physiological contexts. Substantial research and reviews have been done on the role of glucose in disease. This review aims to describe the role of its isomers, fructose and mannose, in the context of inborn errors of metabolism and other metabolic diseases, such as cancer. While structurally similar, fructose and mannose give rise to very differing biochemical properties and understanding these differences will guide the development of more effective therapies for metabolic disease. We will discuss pathophysiology linked to perturbations in fructose and mannose metabolism, diagnostic tools, and treatment options of the diseases. Keywords: fructose and mannose; inborn errors of metabolism; cancer Citation: Lieu, E.L.; Kelekar, N.; Bhalla, P.; Kim, J. Fructose and Mannose in Inborn Errors of Metabolism and Cancer. -
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). -
• for an Anomer, the OH Is Drawn Down. • for a Anomer, the OH Is
How to draw a Haworth projection from an acyclic aldohexose Example: Convert D-mannose into a Haworth projection. CHO HO H HO H H OH H OH CH2OH D-mannose Step [1]: · Draw a hexagon and place the oxygen atom in the upper right corner. O O in upper right corner Step [2]: · Place the anomeric carbon on the first carbon clockwise from the oxygen. · For an anomer, the OH is drawn down. · For a anomer, the OH is drawn up. This C becomes the anomeric C. 1CHO O H O OH HO H 1 1 HO H OH H H OH anomer anomer H OH anomeric carbon - CH2OH first C clockwise from O · Always keep in mind that the anomeric carbon comes from the carbonyl carbon in the acyclic form. Step [3]: · Add the substituents of the three chiral carbons closest to the C=O. · The substituents on the right side of the Fischer projection are drawn down. · The substituents on the left are drawn up. CHO HO 2 H add H O H O H 3 C2 - C4 H HO H 4 OH OH 4 OH OH H 4 OH HO OH HO OH 3 2 3 2 H H H OH H H anomer anomer CH2OH Haworth convention - 2 Step [4]: · For D sugars the CH2OH group is drawn up. For L sugars the CH2OH group is drawn down. CHO CH2OH CH2OH HO H H O H H O H H HO H H OH OH OH OH H OH HO OH HO OH H H H OH H H anomer anomer CH2OH This OH on the right side CH OH is drawn up. -
Structures of Monosaccharides Hemiacetals
Disaccharides 10:51 AM 1 Disaccharides Definition • Disaccharides are carbohydrates consisting of two monosaccharide units linked via a glycosidic bond. Non-reducing disaccharide (1,1'-Glycosidic linkage) OH HO OH O HO O OH O OH OH HO OH HO O O HO OH + HO OH Glycosidic bond OH OH HO OH HO OH 6' 6 O O Reducing end 5' 1' 4 5 HO 4' O OH 3' 2' 3 2 1 HO OH HO OH Glycone Aglycone Reducing disaccharide (1,4'-Glycosidic linkage) • These disaccharides may be reducing or non-reducing sugars depending on the regiochemistry of the glycosidic 10:51 AM linkage between the two monosaccharides. 2 Nomenclature of Disaccharides • Since disaccharides are glycosides with two monosaccharide units linked through a glycosidic bond, their nomenclature requires the formulation of priority rules to identify which of the two monosaccharides of a disaccharide provides the parent name of the disaccharide and which one will be considered the substituent. • The nomenclature of disaccharides is based on the following considerations: i. Disaccharides with a free hemiacetal group (Reducing disaccharide) ii. Disaccharides without a free hemiacetal group (Non- Reducing Disaccharide) 10:51 AM 3 Nomenclature of Reducing Disaccharides • A disaccharide in which one glycosyl unit appears to have replaced the hydrogen atom of a hydroxyl group of the other is named as a glycosylglycose. The locants of the glycosidic linkage and the anomeric descriptor(s) must be given in the full name. • The parent sugar residue in such a reducing disaccharide is chosen on the basis of the following criteria: • The parent sugar residue is the one that includes the functional group most preferred by general principles of organic nomenclature. -
Effects of Sugars and Sugar Alcohols on the Gelatinization Temperatures of Wheat, Potato, and Corn Starches
foods Article Effects of Sugars and Sugar Alcohols on the Gelatinization Temperatures of Wheat, Potato, and Corn Starches Matthew C. Allan, MaryClaire Chamberlain and Lisa J. Mauer * Department of Food Science, Purdue University, 745 Agriculture Mall Drive, West Lafayette, IN 47907, USA; [email protected] (M.C.A.); [email protected] (M.C.) * Correspondence: [email protected]; Tel.: +1-(765)-494-9111 Received: 13 May 2020; Accepted: 3 June 2020; Published: 8 June 2020 Abstract: The gelatinization temperature (Tgel) of starch increases in the presence of sweeteners due to sweetener-starch intermolecular interactions in the amorphous regions of starch. Different starch botanical sources contain different starch architectures, which may alter sweetener-starch interactions and the effects of sweeteners on Tgels. To document these effects, the Tgels of wheat, potato, waxy corn, dent corn, and 50% and 70% high amylose corn starches were determined in the presence of eleven different sweeteners and varying sweetener concentrations. Tgels of 2:1 sweetener solution:starch slurries were measured using differential scanning calorimetry. The extent of Tgel elevation was affected by both starch and sweetener type. Tgels of wheat and dent corn starches increased the most, while Tgels of high amylose corn starches were the least affected. Fructose increased Tgels the least, and isomalt and isomaltulose increased Tgels the most. Overall, starch Tgels increased more with increasing sweetener concentration, molar volume, molecular weight, and number of equatorial and exocyclic hydroxyl groups. Starches containing more short amylopectin chains, fewer amylopectin chains that span through multiple clusters, higher number of building blocks per cluster, and shorter inter-block chain lengths exhibited the largest Tgel increases in sweetener solutions, attributed to less stable crystalline regions. -
D-Mannose Treatment Neither Affects Uropathogenic Escherichia Coli
molecules Article d-Mannose Treatment neither Affects Uropathogenic Escherichia coli Properties nor Induces Stable FimH Modifications 1,2, 3,4, 1 5,6 Daniela Scribano y , Meysam Sarshar y , Carla Prezioso , Marco Lucarelli , 5 1 3,7, 7, , Antonio Angeloni , Carlo Zagaglia , Anna Teresa Palamara y and Cecilia Ambrosi y * 1 Department of Public Health and Infectious Diseases, Sapienza University of Rome, 00185 Rome, Italy; [email protected] (D.S.); [email protected] (C.P.); [email protected] (C.Z.) 2 Dani Di Giò Foundation-Onlus, 00193 Rome, Italy 3 Department of Public Health and Infectious Diseases, Sapienza University of Rome, Laboratory Affiliated to Institute Pasteur Italia-Cenci Bolognetti Foundation, 00185 Rome, Italy; [email protected] (M.S.); [email protected] (A.T.P.) 4 Microbiology Research Center (MRC), Pasteur Institute of Iran, Tehran 1316943551, Iran 5 Department of Experimental Medicine, Sapienza University of Rome, 00185 Rome, Italy; [email protected] (M.L.); [email protected] (A.A.) 6 Pasteur Institute Cenci Bolognetti Foundation, 00161 Rome, Italy 7 IRCCS San Raffaele Pisana, Department of Human Sciences and Promotion of the Quality of Life, San Raffaele Roma Open University, 00166 Rome, Italy * Correspondence: [email protected]; Tel.: +39-06-4991-4622 These authors contributed equally to this work. y Academic Editor: László Somsák Received: 19 December 2019; Accepted: 10 January 2020; Published: 13 January 2020 Abstract: Urinary tract infections (UTIs) are mainly caused by uropathogenic Escherichia coli (UPEC). Acute and recurrent UTIs are commonly treated with antibiotics, the efficacy of which is limited by the emergence of antibiotic resistant strains. -
Using Glycosidases to Remove, Trim, Or Modify Glycans on Therapeutic Proteins
February 2016 | Volume 14 | Number 2 www.bioprocessintl.com www.bioprocessintl.com Covering the Whole Development Process for the Global Biotechnology Industry BioProcess International BioProcess FOCUS ON TECHNICAL ARTICLES Vol.14 No.2 February 2016 February No.2 Vol.14 Facing the 483: What to Do? Detecting Impurities: High- Throughput Method Evaluation BridgingUsing Analytical Glycosidases Methods for to Remove, Trim, or Release and Stability TestingEllen P. Guthrie andModifying Paula E. Magnelli Glycans Using Glycosidases Real EstateModify Challenges Glycans in on Therapeutic Proteins Developing Markets Development of a Plant HCP Assay SPECIAL REPORT: CMC Strategy Forum Tackles Process Impurities 14-2-Cover.indd 1 1/13/16 9:59 AM B IOP ROCESS TECHNICAL Using Glycosidases to Remove, Trim, or Modify Glycans on Therapeutic Proteins Ellen P. Guthrie and Paula E. Magnelli ne of the most common Figure 1: Glycoforms identified by LC/MS analysis of intact Erbitux (cetuximab) digested with PNGase F posttranslational modifications of eukaryotic 13.89 Fucose O proteins is glycosylation. 20 Mannose Glycosylation of proteins can affect 18 Sialic acid (NANA) many biological activities. For 16 GlcNAc 15.12 therapeutic glycoproteins, it can 14 Galactose modify biological activity, targeting, 12 Sialic acid (NGNA) trafficking, serum half life, clearance, 10 18.59 and recognition by receptors (1, 2). For (Fluorescence Trace) (Fluorescence 8 6 Or such reasons, biomanufacturers must 10 6 × monitor and characterize the 4 glycosylation patterns of their 19.41 2 11.34 25.02 recombinant therapeutic proteins (3, 4). Counts 9.33 16.37 24.23 27.50 30.99 34.46 37.87 two 0 Therapeutic proteins have 10 15 20 25 30 35 40 main types of glycosylation : N-linked Time (min) glycans and O-linked glycans (5). -
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. -
20H-Carbohydrates.Pdf
Carbohydrates Carbohydrates are compounds that have the general formula CnH2nOn Because CnH2nOn can also be written Cn(H2O)n, they appear to be “hydrates of carbon” Carbohydrates are also called “sugars” or “saccharides” Carbohydrates can be either aldoses (ald is for aldehyde and ose means a carbohydrate) or ketoses (ket is for ketone) OH OH O OH CH2OH CH2OH OHC HOH2C OH OH OH OH An Aldose A Ketose (D-Glucose) (D-Fructose) Carbohydrates Due to the multiple chiral centers along a linear carbon chain for carbohydrates, Emil Fischer developed the “Fischer Projection” in order to represent these compounds Remember how to draw a Fischer projection: 1) View the linear carbon chain along the vertical axis (always place the more oxidized carbon [aldehyde in an aldose] towards the top) 2) The horizontal lines are coming out of the page toward the viewer 3) Will need to change the viewpoint for each carbon so the horizontal substituents are always pointing towards the viewer CHO OH OH H OH HO H CH2OH = OHC H OH OH OH H OH CH2OH Emil Fischer (1852-1919) Carbohydrates The aldoses are thus all related by having an aldehyde group at one end, a primary alcohol group at the other end, and the two ends connected by a series of H-C-OH groups CHO CHO CHO CHO CHO H OH H OH H OH H OH HO H CH2OH H OH H OH H OH HO H CH2OH H OH H OH HO H CH2OH H OH HO H CH2OH CH2OH Aldotriose Aldotetrose Aldopentose Aldohexose Aldohexose D-glyceraldehyde D-erythose D-ribose D-allose L-allose The D-aldoses are named according to glyceraldehyde, the D refers to the configurational -
THE USE of MONOSACCHARIDES, DISACCHARIDES, and TRISACCHARIDES in SYNTHETIC DILUENTS for the STORAGE of RAM SPERMATOZOA at 37°C and 5°C by K
THE USE OF MONOSACCHARIDES, DISACCHARIDES, AND TRISACCHARIDES IN SYNTHETIC DILUENTS FOR THE STORAGE OF RAM SPERMATOZOA AT 37°C AND 5°C By K. R. LAPWOOD* and 1. C. A. MARTIN* [Manuscript received January 19, 1966] Summary Using synthetic semen diluents based on 20 mM phosphate buffer, 31 mM N aCl, 0·8 % non.dialysable skim milk solids, plus antibiotics, and 185 mM of the sugars ribose, arabinose, xylose, glucose, mannose, fructose, galactose, rhamnose, maltose, lactose, sucrose, or raffinose, it was found that ram spermatozoa survive best at 37°C in diluents containing glucose, mannose, fructose, or sucrose; however, at 5°C ribose, arabinose, xylose, and galactose were the sugars of choice. Increasing replacement of fructose in the diluent with up to 185 mM of these sugars resulted in increased survival at the respective temperatures. Part replacement of 185 mM fructose in the range 7·75-62 mM with the sugars most favourable at 5°C was of little benefit. No effect of changes in osmotic pressure was noted using varying concentrations of the sugars to give tonicities of 0·9, 1· 0, and 1 ·1 relative to 154 mM NaCI or 308 mM sugar. Increased motility scores and percentages of motile sperma· tozoa were observed when 17 mM fructose was added to ribose and arabinose diluents at 5°C, but not when added to diluents containing xylose, the hexoses, galactose, fructose, and glucose; nor for any sugar· containing diluent at 37°C. 1. INTRODUCTION Since the earlier work of Emmens and Blackshaw (1950), who found that the addition of sugars, particularly pentoses, improved revival of mammalian sperma tozoa after deep-freezing, viability and fertility studies have shown that the addition of various sugars to semen diluents improve spermatozoal survival at temperatures of approximately 37 and 5°C for the bull, ram, and cock.