Questions- Carbohydrates A. the Following Structure Is D-Sorbose
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The Role of Biocatalysis in the Asymmetric Synthesis of Alkaloids – an Update Cite This: RSC Adv.,2021,11, 28223 Emmanuel Cigan, † Bettina Eggbauer, † Joerg H
RSC Advances REVIEW View Article Online View Journal | View Issue The role of biocatalysis in the asymmetric synthesis of alkaloids – an update Cite this: RSC Adv.,2021,11, 28223 Emmanuel Cigan, † Bettina Eggbauer, † Joerg H. Schrittwieser * and Wolfgang Kroutil Alkaloids are a group of natural products with interesting pharmacological properties and a long history of medicinal application. Their complex molecular structures have fascinated chemists for decades, and their total synthesis still poses a considerable challenge. In a previous review, we have illustrated how biocatalysis can make valuable contributions to the asymmetric synthesis of alkaloids. The chemo-enzymatic strategies discussed therein have been further explored and improved in recent years, and advances in amine Received 29th May 2021 biocatalysis have vastly expanded the opportunities for incorporating enzymes into synthetic routes Accepted 30th July 2021 towards these important natural products. The present review summarises modern developments in DOI: 10.1039/d1ra04181a chemo-enzymatic alkaloid synthesis since 2013, in which the biocatalytic transformations continue to rsc.li/rsc-advances take an increasingly ‘central’ role. Creative Commons Attribution 3.0 Unported Licence. 1 Introduction originally derived – but also amides, nitro, and nitroso compounds, while excluding primary metabolites such as The alkaloids are a large and structurally diverse group of amino acids, proteins, and porphyrins.1a,d Between 25 000 and nitrogen-containing secondary metabolites that -
Supporting Online Material
1 SUPPLEMENTARY MATERIAL 2 The glycan alphabet is not universal: a hypothesis 3 4 Jaya Srivastava1*, P. Sunthar2 and Petety V. Balaji1 5 6 1Department of Biosciences and Bioengineering, Indian Institute of 7 Technology Bombay, Powai, Mumbai 400076, India 8 9 2Department of Chemical Engineering, Indian Institute of Technology 10 Bombay, Powai, Mumbai 400076, India 11 12 *Corresponding author 13 Email: [email protected] 1 14 CONTENTS Data Description Figure S1 Number of organisms with different number of strains sequenced Figure S2 Biosynthesis pathways Figure S3 Proteome sizes for different number of monosaccharides Figure S4 Prevalence of monosaccharides in species versus that in genomes Figure S5 Bit score distribution plots for hits of various pairs of profiles Table S1 Tools and databases used in this study References References cited in Table S1 Table S2 Comparison of the precursor and nucleotide used for the biosynthesis of two enantiomers of a monosaccharide Flowchart S1 Procedure used to generate HMM profiles Flowchart S2 Precedence rules for assigning annotation to proteins that are hits to two or more profiles and/or BLASTp queries References References to the research articles which describe the pathways (or enzymes of the pathways) of monosaccharide biosynthesis. These formed the basis for generating HMM profiles and choosing BLASTp queries. 15 16 MS-EXCEL file provided separately: Supplementary Data.xlsx 17 Worksheet1 Details of HMM profiles Worksheet2 Details of BLASTp queries Worksheet3 Prevalence of monosaccharides in genomes / species Worksheet4 Abbreviated names of monosaccharides Worksheet5 Enzyme types, enzymes and monosaccharide groups Worksheet6 Precursors of various monosaccharides 18 2 19 Figure S1 The number of species for which different number of strains are sequenced. -
Low Fructose Diet
Low Fructose Diet What is Fructose? Fructose is a naturally occurring simple sugar found in fruit, vegetables, and honey. Fructose intolerance can occur in people with irritable bowel syndrome and other GI disorders. Fruits and fruit juices with higher levels of fructose may cause gas, bloating, abdominal cramping, and diarrhea. Glucose is also a naturally occurring sugar. The more glucose than fructose in a product, the more “intestinal friendly” the fruit or fruit juice may be. High Fructose Corn Syrup (HFCS) **** HFCS is made up of almost half glucose and half fructose and may be absorbed just as well as sucrose (regular table sugar). Therefore, items with HFCS such as soft drinks, may be tolerated well when limited to 12 oz per day and with a meal. HFCS can also be found in canned, baked, or processed foods. **** In some patients, even a small amount of processed fruit juice or even foods with HFCS may cause as much malabsorption, and/or intestinal discomfort, as eating large quantities of fruit. Sorbitol Sorbitol or Sorbose is a sugar alcohol used as an artificial sweetener and found naturally in fruits and fruit juices. It can also be found in many “diet foods” such as diet soft drinks, sugarless gum, sugar-free jelly/jam, and liquid medications. Sorbitol often creates similar symptoms as fructose – especially when fructose and sorbitol are ingested together. General Guidelines • Eliminate products with ingredients that list fructose, crystalline fructose (not HFCS), honey, and sorbitol on the label. • Avoid sugar alcohols which include sorbitol, isomalt, lactitol, maltitol, mannitol, xylitol, erythrytol, and lactatol. -
Evidence for Two Asymmetric Conformational States in the Human Erythrocyte Sugar-Transport System by JOHN E
Biochem. J. (1975) 145, 417429 417 Printed in Great Britain Evidence for Two Asymmetric Conformational States in the Human Erythrocyte Sugar-Transport System By JOHN E. G. BARNETT, GEOFFREY D. HOLMAN, R. ALAN CHALKLEY and KENNETH A. MUNDAY Department ofPhysiology and Biochlemistry, University ofSouthampton, Southampton S09 3TU, U.K. (Received 4 June 1974) 6-0-Methyl-, 6-0-propyl-, 6-0-pentyl- and 6-0-benzyl-D-galactose, and 6-0-methyl-, 6-0-propyl- and 6-0-pentyl-D-glucose inhibit the glucose-transport system of the human erythrocyte when added to the external medium. Penetration of 6-0-methyl-D-galactose is inhibited by D-glucose, suggesting that it is transported by the glucose-transport system, but the longer-chain 6-0-alkyl-D-galactoses penetrate by a slower D-glucose- insensitive route at rates proportional to their olive oil/water partition coefficients. 6-0-n-Propyl-D-glucose and 6-0-n-propyl-D-galactose do not significantly inhibit L-sorbose entry or D-glucose exit when present only on the inside of the cells whereas propyl-f6-D-glucopyranoside, which also penetrates the membrane slowly by a glucose- insensitive route, only inhibits L-sorbose entry or D-glucose exit when present inside the cells, and not when on the outside. The 6-0-alkyl-D-galactoses, like the other non- transported C4 and C-6 derivatives, maltose and 4,6-0-ethylidene-D-glucose, protect against fluorodinitrobenzene inactivation, whereas propyl ,B-D-glucopyranoside stimulates the inactivation. Of the transported sugars tested, those modified at C-1, C-2 and C-3 enhance fluorodinitrobenzene inactivation, where those modified at C-4 and C-6 do not, but are inert or protect against inactivation. -
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). -
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 -
The Food Lawyers® Respectfully Request That FDA Implements the Following
December 7, 2020 Dockets Management Staff (HFA-305) Filed Electronically Food and Drug Administration https://www.regulations.gov Re: Sugars Metabolized Differently than Traditional Sugars (FDA-2020-N-1359) Ladies and Gentlemen: One Page Executive Summary FDA’s seeks information to “… promote the public health and help consumers make informed dietary decisions” regarding sugars that are metabolized differently than traditional sugars. Given the nation’s battles with diabetes and obesity, and the benefits that non-traditional sugars can offer in these battles, the Agency’s stated public policy goal goes to the very heart of American consumers’ health. This laudatory public policy’s realization is complicated by a lack of consumer awareness of how some sugars are metabolized differently than others. In an effort to answer the questions posed by the Agency regarding the treatment of Sugars that Are Metabolized Differently Than Traditional Sugars, we suggest that the Agency adapt a mechanism that will seek to harmonize the public policy of promoting public health with consumers’ lack of awareness of sugars that are metabolized differently than sucrose. In particular, we suggest that FDA should consider the following: 1. Establish a new category of sugars called Rare Sugars that exhibit the following characteristics: a. Are naturally occurring b. Impart a sweet taste that is at least 50% the sweetness of sucrose c. 2.0 kcal/g or less. d. Resulting pH of 6.0 or greater of dental plaque after consumption. e. No or low glycemic response. f. No or low insulinemic response. 2. Exclude Rare Sugars from “Total Sugars” and “Added Sugars” declarations to stimulate their deployment by industry and consumption by the public. -
1) Which of the Following Biomolecules Simply Refers to As “Staff of Life”? (A) Lipids (B) Proteins (C) Vitamins (D) Carbohydrates Sol: (D) Carbohydrates
1) Which of the following Biomolecules simply refers to as “Staff of life”? (a) Lipids (b) Proteins (c) Vitamins (d) Carbohydrates Sol: (d) Carbohydrates. 2) Which of the following is the simplest form of carbohydrates? (a) Carboxyl groups (b) Aldehyde and Ketone groups (c) Alcohol and Carboxyl groups (d) Hydroxyl groups and Hydrogen groups Sol: (b) Aldehyde and Ketone groups. 3) Which of the following monosaccharides is the majority found in the human body? (a) D-type (b) L-type (c) LD-types (d) None of the above Sol: (a) D-type. 4) Which of the following is the most abundant biomolecule on the earth? (a) Lipids (b) Proteins (c) Carbohydrates (d) Nucleic acids. Sol: (c) Carbohydrates. 5) Which of the following are the major functions of Carbohydrates? (a) Storage (b) Structural framework (c) Transport Materials (d) Both Storage and structural framework Sol: (d) Both Storage and structural framework. 6) Which of the following is the general formula of Carbohydrates? (a) (C4H2O)n (b) (C6H2O)n (c) (CH2O)n (d) (C2H2O)n COOH Sol: (c) (CH2O)n. 7) Which of the following is the smallest carbohydrate – triose? (a) Ribose (b) Glucose (c) Glyceraldehyde (d) Dihydroxyacetone Sol: (c) Glyceraldehyde. 8) Which of the following is a reducing sugar? (a) Dihydroxyacetone (b) Erythrulose (c) Glucose (d) All of the above Sol: (c) Glucose. 9) Which of the following is an example of Epimers? (a) Glucose and Ribose (b) Glucose and Galactose (c) Galactose, Mannose and Glucose (d) Glucose, Ribose and Mannose Sol: (b) Glucose and Galactose 10) Which of the following has reducing properties? (a) Mucic acid (b) Glucaric acid (c) Gluconic acid (d) Glucuronic acid Sol: (d) Glucuronic acid. -
Converting Galactose Into the Rare Sugar Talose with Cellobiose 2-Epimerase As Biocatalyst
molecules Article Converting Galactose into the Rare Sugar Talose with Cellobiose 2-Epimerase as Biocatalyst Stevie Van Overtveldt, Ophelia Gevaert, Martijn Cherlet, Koen Beerens and Tom Desmet * Centre for Synthetic Biology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Gent, Belgium; [email protected] (S.V.O.); [email protected] (O.G.); [email protected] (M.C.); [email protected] (K.B.) * Correspondence: [email protected]; Tel.: +32-9264-9920 Academic Editors: Giorgia Oliviero and Nicola Borbone Received: 17 September 2018; Accepted: 29 September 2018; Published: 1 October 2018 Abstract: Cellobiose 2-epimerase from Rhodothermus marinus (RmCE) reversibly converts a glucose residue to a mannose residue at the reducing end of β-1,4-linked oligosaccharides. In this study, the monosaccharide specificity of RmCE has been mapped and the synthesis of D-talose from D-galactose was discovered, a reaction not yet known to occur in nature. Moreover, the conversion is industrially relevant, as talose and its derivatives have been reported to possess important antimicrobial and anti-inflammatory properties. As the enzyme also catalyzes the keto-aldo isomerization of galactose to tagatose as a minor side reaction, the purity of talose was found to decrease over time. After process optimization, 23 g/L of talose could be obtained with a product purity of 86% and a yield of 8.5% (starting from 4 g (24 mmol) of galactose). However, higher purities and concentrations can be reached by decreasing and increasing the reaction time, respectively. In addition, two engineering attempts have also been performed. -
WO 2013/070444 Al 16 May 2013 (16.05.2013) W P O P C T
(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2013/070444 Al 16 May 2013 (16.05.2013) W P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A23G 4/00 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/US20 12/062043 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, 26 October 2012 (26.10.2012) KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (25) Filing Language: English NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, (26) Publication Language: English RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, (30) Priority Data: ZM, ZW. 61/556,546 7 November 20 11 (07. 11.201 1) US (84) Designated States (unless otherwise indicated, for every (71) Applicant (for all designated States except US): WVI. kind of regional protection available): ARIPO (BW, GH, WRIGLEY JR. COMPANY [US/US]; 1132 Blackhawk GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, Street, Chicago, IL 60642 (US). -
Total Synthesis of Aspeverin and Penicimutamide a Part Ii
PART I: TOTAL SYNTHESIS OF ASPEVERIN AND PENICIMUTAMIDE A PART II: TOTAL CHEMICAL SYNTHESIS OF ALL-L AND ALL-D KRAS(G12V) AND THE FURTHER EXPLORATION OF ISONITRILE- MEDIATED PEPTIDE LIGATIONS A Dissertation Presented to the Faculty of the Weill Cornell Graduate School of Medical Sciences in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy by Adam M. Levinson January 2017 © Adam M. Levinson 2016 PART I: TOTAL SYNTHESIS OF ASPEVERIN AND PENICIMUTAMIDE A PART II: TOTAL CHEMICAL SYNTHESIS AND FOLDING OF ALL-L AND ALL-D KRAS(G12V) AND THE FURTHER EXPLORATION OF ISONITRILE- MEDIATED PEPTIDE LIGATIONS Adam M. Levinson Cornell University 2016 Part I: Fungi serve as a rich source of prenylated indole alkaloids, which exhibit important biological activities including antiproliferative, antibiotic, and antihelminthic properties. Their promise as therapeutics, coupled with their diverse and complex molecular architectures, have made prenylated indole alkaloids popular targets for synthetic chemists in order to probe their activities and develop new synthetic methods. Herein, we describe the first total synthesis of aspeverin, a unique bridged carbamate-containing prenylated indole alkaloid isolated from Aspergillus versicolor. We also describe the synthesis of a closely related congener, penicimutamide A, isolated from a mutant strain of Penicillium purpurogenum. These molecules belong to a recently described subclass of prenylated indoles thought to be degradation products of parent bicyclo[2.2.2]diazaoctane congeners. In this research, we showcase a highly diastereoselective Diels−Alder cycloaddition, followed by an electrophilic Rawal arylation – reductive indolization to forge the pentacyclic scaffold of these natural products. A novel sequence for installation of a geminal dimethyl group was also developed. -
Screening of Candidate Substrates and Coupling Ions of Transporters By
TOOLS AND RESOURCES Screening of candidate substrates and coupling ions of transporters by thermostability shift assays Homa Majd1†, Martin S King1†, Shane M Palmer1, Anthony C Smith1, Liam DH Elbourne2, Ian T Paulsen2, David Sharples3,4, Peter JF Henderson3,4, Edmund RS Kunji1* 1Medical Research Council Mitochondrial Biology Unit, University of Cambridge, Cambridge, United Kingdom; 2Department of Molecular Sciences, Macquarie University, Sydney, Australia; 3Astbury Centre for Structural Molecular Biology, University of Leeds, Leeds, United Kingdom; 4School of Biomedical Sciences, University of Leeds, Leeds, United Kingdom Abstract Substrates of most transport proteins have not been identified, limiting our understanding of their role in physiology and disease. Traditional identification methods use transport assays with radioactive compounds, but they are technically challenging and many compounds are unavailable in radioactive form or are prohibitively expensive, precluding large- scale trials. Here, we present a high-throughput screening method that can identify candidate substrates from libraries of unlabeled compounds. The assay is based on the principle that transport proteins recognize substrates through specific interactions, which lead to enhanced stabilization of the transporter population in thermostability shift assays. Representatives of three different transporter (super)families were tested, which differ in structure as well as transport and ion coupling mechanisms. In each case, the substrates were identified correctly from a large set of *For correspondence: chemically related compounds, including stereo-isoforms. In some cases, stabilization by substrate [email protected] binding was enhanced further by ions, providing testable hypotheses on energy coupling †These authors contributed mechanisms. equally to this work DOI: https://doi.org/10.7554/eLife.38821.001 Competing interests: The authors declare that no competing interests exist.