DOCSLIB.ORG

Synthesis of Lactose-1-C^14 and Lactobionic-1-C^14-Delta Lactone

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Synthesis of Lactose-1-C^14 and Lactobionic-1-C^14-Delta Lactone Journal of Research of the Nationa l Bureau of Standards Vol. 50, No.3, March 1953 Research Paper 2400 Synthesis of Lactose-I-C14 and Lactobionic-I-C 14 Delta Lactone From 3.f3-D-Galactopyranosyl-a-D-Arabinose I Harriet L. Frush and Horace S. Isbell Lact ose-I-CH, which has been prepared for t he first time, was obtained in 38-percent radiochemical yield by the cyanohydrin synthesis with 3- (JS-D-galactopyranosyl)-n-arabinose. The latter substance was prepared in crystalline form and its reaction with N a CH]'\ was studied under a variety of conditions. Acid catalysts favor production of the epimer having the mannose configuration. An improved procedure is given for the lactonization of lactobionic acid; by slow crystallizat ion from methyl cellosolve, large crystals of high-purity lact obionic-I-C14 delta lactone were obtained . The lact one was reduced to lactose by sodium amalgam in the presence of sodium acid oxalate with a yield (by analysis) of 84 percent. A modification of the process in which the separation of the epimeric acids or lact ones is omitted, was also found t o be practicable for t he production of lactose-I-CIl. 1. Introduction To provide a basis for directing the cyanohydrin reaction to lactobionic nitrile rather than to 4-galac­ There are many unsolved problems in human and tosyl-mannonic nitrile, the condensation of 3-galac­ animal nutrition that can be attacked by means of tosyl-arabinose with cyanide was studied by means of certain position-labeled carbohydrates. Lactose, one a tracer technique. Tlli involved conden ation of of the most important of these carbohydrates, has no t the sugar with labeled cyanide in buffered solution , heretofore been available in radioactive form. This hydrolysis of the cyanohydrins, and separation of the paper repOTts the preparation of high-activity labeled lactobionic acid as the calcium lactobionate I-Ou-Iabeled lactose in good yield by means of a calcium bromide double alt [4] . It was found that cyanohydrin synthesis on 3-galactosyl-arabinose. sodium bicarbonate and presumably other general acid catalysts in the cyanohydrin mixture favor 2 . Discussion of the Experimental Method formation of the 4-galacto yl-mannonic epimer; cal­ cium chloride or sodium carbonate, however , favor The over-all plan for the production of labeled formation of the 4-galacto yl-gluconic (lactobionic) lactose consisted of the following steps: epimer. These results obtained by tracer methods, Lactose correspond qualitatively to those obtained by optical rotation and isolation methods in the tudy of the 1E lectrolytic oxidation [1] 2 cyanohydrin synthe i for the production of D-glu­ cose-I-Ol4 and D-mannose-l-0 14 from D-arabinosc [5]­ Calcium lactobionate In the preparation of labeled lactose, both the cal­ H 20 2+ Fe+++ [2] cium chloride method [6], and the sodium carbonate 1 method for conducting the cyanide condensation 3-(JS-D-Galactopyrano yl)-D-arabino e 3 were used, but the lat ter is preferable because it Cyanohydrin reaction avoids the introduction and subsequent troublesome 1 removal of the chloride ion. In early preparations Epimeric nitriles by the calcium chloride method, lactobionic acid wa isolated from the cyanohydrin hydrolyzate as the 1H ydrolysis crystalline calcium lactooionate calcium chloride Epimeric aldobionic acids double salt [7] . The procedure involved several steps later eliminated by condensation in the presence of Lactonization and sodium carbonate, and crystallization of lactobionic separation of epimers lactone from the hydrolyzate. 'rhe latter step wa r 1 made practicable by the development of a procedure Lactobionic-a-Iactone 4-(JS-D-Galactopyranosyl) for the complete conversion of lactobionic acid to -D-mannonic acid the lactone. 1N aHg", reduction To ascertain favorable conditions for reduction of the lactone to lactose, numerous samples of nonradio­ 1Cry tallization active lactobiomc delta lactone were reduced with Lactose-I-CH various quantities of sodium amalgam in the presence 1 Part of a project on the development of methods for the synthesis of radIo­ of sodium acid oxalate. The reduction wa con­ active carbohydrates, spon80red by the Atomic Energy Co=ission . ducted in the apparatus described previously [5], but • Figures in brackets indicate t.he literature references at the end of this paper. • The alpha modification of this sugar, 3·(p·D·galactopyranosyl)·a·D·arahinose modified by a sidearm that permitted addition of had been crystallized several years ago by Zempl ~ u [31 , but no seed crystals were available in this laboratory. However, after abo ut 2 months, crystals were ob­ amalgam while the solution was being tin'ed. It tained from a sirup containing methyl cellosolve aud isopropyl ether. There­ was found by analysis that, under suitable conditions, after, crystallization of other preparations was readily effected by use of seed crystals. 84 percent of the lactone i converted to the sugar. 133 After removal of sodimTI salts, the lactose was sep­ anion exchange resins.' The combined efRuent and al'ated by crystallization from aqueous methanol wash liquor was evaporated under reduced pressure with the addition of isopropanol. In radioactive to a thick sirup, which was dissolved in about 50 ml preparations, additional labeled sugar was recovered of methvl cellosolve. From this solution several from the mother liquor by the carrier technique. In frac tions" of siruP? 3-galactosyl-arabinose were pre­ a preparation starting with 3.5 mc of C14-labeled cipitated by the addition of isopropyl ether. Each sodium cyanide the yield of labeled lactobionic delta of the fraction s was dissolved in methyl cellosolve lactone was 54 percent. In the reduction step 68 and th e solutions, brought to incipient turbidity by percent of th e lactone was isolated as crys talline means of isoprop:d ether, wer e stored in a desiccator lactose. The over-all radiochemical yield of lactose- over calcium chloride. After 2 months, the sirupy 1-C14 was thus 37 percen t. residue of one fraction crystallized. The r emaining It was also found practicable to prepare lactose fractions crystallized when seeded, and a total of without the separation and purification of any inter­ 50 g of crude crystalline 3-(j3 -D-galactopy-ranosyl)-a-D­ mediate, by reducing the crude lactone mixture pre­ arabinose was obtained. To r ecrystalliz e, the mate­ pared from the cyanohydrin reaction. The resulting rial was dissolved in a minimum of hot water, and solution gave one crop of crystalline lactose without the solution was filt ered with the aid of deeolorizin6 carrier ; additional crops, obtained by use of carriers, carbon and treated 'with isopropanol almost to the raised the radioch emical yield to 38 percent. point of turbidity. It was also recrystalliz ed from a thick aqueous sirup (80° Brix) by the addition of 3. 'Experimental Details m ethyl cellosolve. [albD of the purified product was - 62.5 0 at equilibrium (water , c= 2) in approximate 3.1. Preparation of 3-(j3 -D-Galactopyranosyl)- a-D­ agreement with the value previously reported by Arabinose Zemplen [3] ([al1D= - 50 .3°"""'-63. 1°). A mixture of 375 g of calcium lactobionate penta­ 3.2. Epimeric Proportions of the Products Formed by hydrate, 20 g of barium acetate monohydrate, and Condensation of 3- (j3 -D-Galactopyronosyl)-D-aro­ 10 g of ferric sulfate (with abou t 6H20 ), was added to 3 liters of boiling wa ter [2]. The mixture was binose with Cyanide cooled to 350 C, and 120 ml of 30-percent hydrogen The experiments outlined in table 1 were conducted peroxide was added . During the ensuing reaction to determine optimum conditions for the formation period, the solution was cooled to maintain a temp­ of the lactobionic epimer. In each experimen t 2 ml erature of less than 50 ° C. After about 1 hI' the of a solution containing 0.0636 millimole of 0 14_ solution, which had turned darI-.: bn~)\vn , was cooled labeled cyanide with 5.12 J1.c of activity was placed to 40° C, and a second 120-ml portlOn of hydro!$en in a glass-stoppered tube. The solution was frozen peroxide was added. ,Vhen the seco.n~ reactlOn in a carbon dioxid e-ace tone freezing mixture to pre­ was complete, about 25 g of a decolol1zmg carbon ven t loss of cyanidc, after which 2 ml of a solution, and 10 g of eal ci~m carbonate were added. The containing 0.0705 millimole of 3-galactosyl-arabinose mixture was filtered , and the fil trate was evaporated and the v arious substances listed in table 1, was under reduced pressure t o a sirup of about 80-percen t introduced . The mixture was shaken gently until total solids. The sirup was mixed first with 300 ml the ice dissolved and was then allowed to stand at of methanol and then 600 ml of a 1: 1 mixture of room temperature. After 48 hI', th e mixture was methanol a~d ethanol was added. The resulting heatcd at 80° C for 5 hI' to eff ect hydrolysis, and precipitate was separated by fil ~ra t ion , and was then was evaporated to dryn ess in an air stream. wash ed, fu'st on the filter, then III a beaker, and T he residue in each tube was dissolved in a few drops finally on the 6.1te l' with a total of 500 ml of ethanol. of water, and the solution was neu tralized to the The r esidue 'was discarded. The filtrate and wash end point of phenolphthalein by the addition of liquor deposited some gummy material fr~m which dilu te hydrobromic acid. N omadioactive calcium the clear liquid was decanted . The r esIdue was lactobionate calcium bromid e (531.3 mg of Ca triturated with 100 ml of ethanol, and the ethanol (CI2H 21 0 12 )2 .CaBr2 .6H20 ) [4] was dissolvcd in each hy­ extract was fil ter ed .
Load more

Recommended publications
  • Screening of Lactobionic Acid Producing Microorganisms Hiromi
    469 (J. Appl. Glycosci., Vol. 49, No. 4, p. 469-477 (2002)) Screening of Lactobionic Acid Producing Microorganisms Hiromi Murakami,* Jyunko Kawano,' Hajime Yoshizumi,' Hirofumi Nakano and Sumio Kitahata Osaka Municipal Technical Research Institute (1-6-50, Morinomiya, Joto-ku, Osaka 536-8553, Japan) 1Faculty of Agriculture, Kinki University (3327-204, Nakamachi, Nara 631-8505, Japan) Lactobionic acid (LA) is derived from lactose and expected to be a versatile material for grow- ing bifidobacterium and forming mineral salts with high solubility in water for supplements. We aimed to develop microbial or enzymatic production systems of LA. To this aim, we screened lactose-oxidizing microorganisms, and obtained a strain of Burkholderia cepacia. The lactose- oxidizing activity existed in the membrane fraction of disrupted cell preparation of the strain. Only oxygen was necessary for lactose-oxidizing activity as a proton acceptor. A crude cell-free enzyme preparation was prepared, and its oxidizing ability and other properties on several saccharides were examined. The cell-free preparation oxidized D-glucose, D-mannose, D-galactose, D-xylose, L- arabinose and D-ribose. It also reacted with lactose, cellobiose, maltose, maltotriose, maltotetaose and maltopentaose. The strain accumulated LA in the culture supernatant with no loss of lactose. The strain is advantageous to production of LA by both fermentation and enzymatic reaction. Lactose (Lac), one of the most common saccha- pergillus niger,6,7)Phanerochaete chrysosporium8) rides in dairy products, can be obtained easily and Penicillium chrysogenum .9) These strains and from cheese whey and casein whey, the large pool enzymes will not be used for LA production be- of unutilized resources.
    [Show full text]
  • Production of Lactobionic Acid by Oxidation of Lactose Over Gold Catalysts Supported on Mesoporous Silicas – Reaction Optimization and Purification Process Proposal
    Production of lactobionic acid by oxidation of lactose over gold catalysts supported on mesoporous silicas – Reaction optimization and purification process proposal Thèse Luis Felipe Gutiérrez Doctorat en sciences et technologie des aliments Philosophiae Doctor (Ph.D) Québec, Canada © Luis Felipe Gutiérrez, 2013 Résumé Le surplus mondial et le faible prix du lactose ont attiré l‘attention de chercheurs et de l‘industrie pour développer des procédés novateurs pour la production de dérivés du lactose à valeur ajoutée, tels que l‘acide lactobionique (ALB), qui est un produit à haute valeur ajoutée obtenu par l‘oxydation du lactose, avec d‘excellentes propriétés pour des applications dans les industries alimentaire et pharmaceutique. Des recherches sur la production d‘ALB via l‘oxydation catalytique du lactose avec des catalyseurs à base de palladium et de palladium-bismuth, ont montré des bonnes conversions et sélectivités envers l‘ALB. Cependant, le principal problème de ces catalyseurs est leur instabilité par lixiviation et désactivation par suroxydation au cours de la réaction. Les catalyseurs à base d‘or ont montré une meilleure performance que les catalyseurs de bismuth-palladium pour l‘oxydation de glucides. Cependant, trouver un catalyseur robuste pour l‘oxydation du lactose est encore un grand défi. Dans cette dissertation, des nouveaux catalyseurs à base d‘or supportés sur des matériaux mésostructurés de silicium (Au/MSM) ont été synthétisés par deux méthodes différentes, et évalués comme catalyseurs pour l‘oxydation du lactose. Les catalyseurs ont été caractérisés à l‘aide de la physisorption de l‘azote, DRX, FTIR, TEM et XPS. Les effets des conditions d‘opération, telles que la température, le pH, la charge d‘or et le ratio catalyseur/lactose, sur la conversion du lactose ont été étudiés.
    [Show full text]
  • Erythromycin Lactobionate
    Erythromycin lactobionate sc-279018 Material Safety Data Sheet Hazard Alert Code Key: EXTREME HIGH MODERATE LOW Section 1 - CHEMICAL PRODUCT AND COMPANY IDENTIFICATION PRODUCT NAME Erythromycin lactobionate STATEMENT OF HAZARDOUS NATURE CONSIDERED A HAZARDOUS SUBSTANCE ACCORDING TO OSHA 29 CFR 1910.1200. NFPA FLAMMABILITY1 HEALTH2 HAZARD INSTABILITY0 SUPPLIER Santa Cruz Biotechnology, Inc. 2145 Delaware Avenue Santa Cruz, California 95060 800.457.3801 or 831.457.3800 EMERGENCY ChemWatch Within the US & Canada: 877–715–9305 Outside the US & Canada: +800 2436 2255 (1–800-CHEMCALL) or call +613 9573 3112 SYNONYMS C49-H89-N-O25, C37-H67-N-O13.C12-H22-O12, "lactobionic acid, compd. with erythromycin (1:1)", "erythromycin mono(4-O-beta- D-galactopyranosyl-D-gluconate) salt", "4-O-beta-D-galctopyranosyl-D-gluconic acid compd with erythromycin", "Erythrocin Lactobionate", "macrolide antibiotic" Section 2 - HAZARDS IDENTIFICATION CHEMWATCH HAZARD RATINGS Min Max Flammability: 1 Toxicity: 4 Body Contact: 0 Min/Nil=0 Low=1 Reactivity: 1 Moderate=2 High=3 Chronic: 2 Extreme=4 CANADIAN WHMIS SYMBOLS 1 of 7 EMERGENCY OVERVIEW RISK POTENTIAL HEALTH EFFECTS ACUTE HEALTH EFFECTS SWALLOWED ! Accidental ingestion of the material may be severely damaging to the health of the individual; animal experiments indicate that ingestion of less than 5 gram may be fatal. ! Sensitization of skin resulting in eruptions due to exposure to erythromycin has been reported. Higher concentrations may induce reversible deafness and liver damage, with upper abdominal pain, fever, liver enlargement and raised liver enzymes. ! Macrolides comprise a large group of antibiotics derived from Streptomyces spp. having in common a macrocyclic lactone ring to which one or more sugars are attached.
    [Show full text]
  • Synthesis of the Galactosyl Derivative of Gluconic Acid with the Transglycosylation Activity of Β-Galactosidase
    258 A. WOJCIECHOWSKA et al.: Synthesis of Gluconic Acid Derivative, Food Technol. Biotechnol. 55 (2) 258–265 (2017) ISSN 1330-9862 scientific note doi: 10.17113/ftb.55.02.17.4732 Synthesis of the Galactosyl Derivative of Gluconic Acid With the Transglycosylation Activity of β-Galactosidase Aleksandra Wojciechowska1*, Robert Klewicki1, Michał Sójka1 and Elżbieta Klewicka2 1Institute of Food Technology and Analysis, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Stefanowskiego 4/10, PL-90-924 Łódź, Poland 2Institute of Fermentation Technology and Microbiology, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Wólczańska 171/173, PL-90-924 Łódź, Poland Received: April 7, 2016 Accepted: November 29, 2016 Summary Bionic acids are bioactive compounds demonstrating numerous interesting properties. They are widely produced by chemical or enzymatic oxidation of disaccharides. This pa- per focuses on the galactosyl derivative of gluconic acid as a result of a new method of bi- onic acid synthesis which utilises the transglycosylation properties of β-galactosidase and introduces lactose as a substrate. Products obtained in such a process are characterised by different structures (and, potentially, properties) than those resulting from traditional oxi- dation of disaccharides. The aim of this study is to determine the effect of selected param- eters (concentration and ratio of substrates, dose of the enzyme, time, pH, presence of salts) on the course of the reaction carried out with the enzymatic preparation Lactozym, containing β-galactosidase from Kluyveromyces lactis. Research has shown that increased dry matter content in the baseline solution (up to 50 %, by mass per volume) and an addi- tion of NaCl contribute to higher yield.
    [Show full text]
  • The Current Status and Future Perspectives of Lactobionic Acid Production: a Review
    FOOD SCIENCE DOI: 10.22616/rrd.24.2018.037 THE CURRENT STATUS AND FUTURE PERSPECTIVES OF LACTOBIONIC ACID PRODUCTION: A REVIEW Inga Sarenkova, Inga Ciprovica Latvia University of Life Sciences and Technologies, Latvia [email protected] Abstract Lactobionic acid is a high value added compound industrially produced through energy intensive chemical synthesis, which uses costly metal catalysts, like gold and platinum. In the next years, biotechnological production of lactobionic acid can be supposed to take the full transition to the manufacturing stage. Productivity of lactobionic acid by microbial production can be affected by various factors – choice of microorganism and its concentration, supply of oxygen, temperature, substrate, cultivation method, pH and aeration rate. The aim was to review research findings for lactobionic acid production as well innovative and efficient technology solutions for self-costs reducing. Whey was recommended as a cheap and suitable substrate for the lactobionic acid production. Whey processing has been advised with Pseudonomas teatrolens in 28 °C and in pH 6 to 7 for yielding the highest productivity. The increasing commercial importance urges the progression of schemes for lactobionic acid biotechnological manufacturing. Key words: lactobionic acid, lactose, oxidation. Introduction long lasting production alternative to the expensive Whey is renewable resource in food industry and high intensive energy chemical production way and contains a lot of milk sugar – lactose. Lactose (Alonso, Rendueles, & Diaz, 2011). Pseudomonas takes an important role in nutrition. It is a unique taetrolens shows higher ability of conversion disaccharide widespread in the mammalian milk per unit of organic matter with no complicated (Gutiérrez, Hamoudi, & Belkacemi, 2011; Prazeres, nutrient requirements (Alonso, Rendueles, & Diaz, Carvalho, & Rivas, 2012).
    [Show full text]
  • Antiaging Effects of Topical Lactobionic Acid: Results of a Controlled Usage Study Barbara A
    STUDY Antiaging Effects of Topical Lactobionic Acid: Results of a Controlled Usage Study Barbara A. Green, RPh, MS; Brenda L. Edison, BA; Monya L. Sigler, PhD There are numerous clinical publications supporting the use of traditional a-hydroxy acids (AHAs), including glycolic acid, lactic acid, and citric acid, to counter aging. Studies have demonstrated sig- nificant dermal effects, including increased deposition of glycosaminoglycans, improved elastic fiber quality, and collagen gene induction. These dermal effects provide antiaging benefits to skin. Lacto- bionic acid, a next-generation AHA possessing a polyhydroxy structure (a so-called polyhydroxy acid), has been shown to provide textural and smoothing benefits to skin and to increase skin thickness via digital caliper measurements, thereby providing multiple antiaging benefits. Lactobionic acid is also an antioxidant chelating substance that suppresses matrix metalloproteinase enzymatic activity, helping to protect against further sunCOS damage. Lactobionic acidDERM has also been shown to be gentle to skin without causing the stinging and irritation associated with some AHAs. This study was conducted to assess the efficacy of topical lactobionic acid 8% to reduce the visible signs of aging skin on the face and to deter- mine histologic and dermalDo thickness Not changes on the armCopy during 12 weeks of controlled usage. Results indicate significant improvements in clinically graded parameters, a significant reduction in mild pre- existing irritation, and significant increases in skin firmness and thickness. Histologic examples of reduced matrix metalloproteinase-9 activity and increased staining for glycosaminoglycans were observed. When used alone, either as a preventive or an active treatment, lactobionic acid provides beneficial antiaging effects.
    [Show full text]
  • Lactobionic Acid: Significance and Application in Food and Pharmaceutical Minal, N., Bharwade, Smitha Balakrishnan*, Nisha N
    Intl. J. Food. Ferment. 6(1): 25-33, June 2017 © 2017 New Delhi Publishers. All rights reserved DOI: 10.5958/2321-712X.2017.00003.5 Lactobionic Acid: Significance and Application in Food and Pharmaceutical Minal, N., Bharwade, Smitha Balakrishnan*, Nisha N. Chaudhary and A.K. Jain SMC College of Dairy Science, AAU, Anand, India *Corresponding author: [email protected] Abstract Lactose has long been used as a precursor for the manufacture of high-value derivatives with emerging applications in the food and pharmaceutical industries. This review focuses on the main characteristics, manufacturing methods, physiological effects and applications of lactobionic acid. Lactobionic acid is a product obtained from lactose oxidation, with high potential applications as a bioactive compound. Recent advances in tissue engineering and application of nanotechnology in medical fields have also underlined the increased importance of this organic acid as an important biofunctional agent. Keywords: Lactobionic acid, oxidation, physiological effects, applications Carbohydrates have been used in the manufacture biocompatibility, biodegradability, nontoxicity, of bulk and fine chemicals, and are viewed as a chelating, amphiphilic and antioxidant properties renewable feedstock for the ‘green chemistry of the (Alonso et al., 2013). future. Lactose, a unique disaccharide, occurring extensively in the mammalian milk plays an CHEMISTRY important role in nutrition. Most of the lactose that Lactobionic acid (4-0-β-D-galactopyranosyl-D- is manufactured on an industrial scale is produced gluconic acid) belongs to the aldobionic family of acids from the whey derived from the production of cheese, (Pezzotti and Therisod, 2006). Chemically lactobionic casein or paneer by using drying, crystallization and acid comprises a galactose moiety linked with a purification technologies.
    [Show full text]
  • Hydrates of Erythromycin Salts, the Preparation And
    (19) TZZ ¥Z__T (11) EP 2 301 945 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07H 17/08 (2006.01) A61K 31/7048 (2006.01) 15.10.2014 Bulletin 2014/42 A61P 31/00 (2006.01) (21) Application number: 09793794.0 (86) International application number: PCT/CN2009/000787 (22) Date of filing: 10.07.2009 (87) International publication number: WO 2010/003319 (14.01.2010 Gazette 2010/02) (54) HYDRATES OF ERYTHROMYCIN SALTS, THE PREPARATION AND THE USE THEREOF HYDRATE AUS ERYTHROMYCINSALZEN SOWIE IHRE HERSTELLUNG UND VERWENDUNG HYDRATES DE SELS D’ÉRYTHROMYCINE, LA PRÉPARATION ET L’UTILISATION DE CEUX-CI (84) Designated Contracting States: • DATABASE REGISTRY [Online] CHEMICAL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR ABSTRACTS SERVICE, COLUMBUS, OHIO, US; HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL 16 November 1984 (1984-11-16), XP002662315, PT RO SE SI SK SM TR retrieved from stn accession no. 14444-93-0 Database accession no. 14444-93-0 (30) Priority: 10.07.2008 CN 200810048383 • DATABASE REGISTRY [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; (43) Date of publication of application: 16 November 1984 (1984-11-16), XP002662316, 30.03.2011 Bulletin 2011/13 retrieved from stn accession no. 14550-96-0 Database accession no. 14550-96-0 (73) Proprietor: Liu, Li • DATABASE REGISTRY [Online] CHEMICAL Guangdong 528500 (CN) ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 16 November 1984 (1984-11-16), XP002662317, (72) Inventor: Liu, Li retrieved from stn accession no.
    [Show full text]
  • Lactobionic Acid Produced by Zymomonas Mobilis: Alternative To
    A tica nal eu yt c ic a a m A r a c t Valle et al., Pharmaceut Anal Acta 2013, 4:3 h a P DOI: 10.4172/2153-2435.1000220 ISSN: 2153-2435 Pharmaceutica Analytica Acta Research Article Open Access Lactobionic Acid Produced by Zymomonas mobilis: Alternative to Prepare Targeted Nanoparticles Ticiana Alexandra Valle1, Ângelo Adolfo Ruzza3, Marco Fabio Mastroeni1, Eloane Malvessi2, Maurício Moura da Silveira2, Ozair de Souza4 and Gilmar Sidnei Erzinger1* 1Department of Health and Environment, University of Joinville Region, SC, Brazil 2Biotechnology Institute, University of Caxias do Sul (INBio/UCS), RS, Brazil 3Department of Chemistry University Federal of Santa Catarina, SC, Brazil 4Department of MSc in Process Engineering, University of Joinville Region, SC, Brazil Abstract The bacterium Zymomonas mobilis has the ability to produce several organic acids from mixtures of fructose and different aldoses as an alternative to glucose. One of these organic acids, lactobionic acid, is produced from the oxidation of lactose and is produced in equimolar amounts with sorbitol, a product of fructose reduction. Sorbitol is widely used in the food and pharmaceutical industry, while lactobionic acid has important applications in medicine and cosmetics. It has been reported in the literature that lactobionic acid has the potential for drug vectorization, particularly for anti-tumor drugs. The objective of this work is to show that lactobionic acid produced by Zymomonas mobilis can be used for targeted delivery of chemotherapeutic agents. Using analytical techniques such as HPLC, NMR and polarimetry, we showed that lactobionic acid produced in Zymomonas mobilis is of high purity (100%) when compared to the 97% pure lactobionic acid salt from Sigma®, which was used as a reference.
    [Show full text]
  • Download This Article PDF Format
    RSC Advances View Article Online PAPER View Journal | View Issue Efficient production of sugar-derived aldonic acids by Pseudomonas fragi TCCC11892† Cite this: RSC Adv.,2018,8, 39897 Shuhong Mao, a Yanna Liu,b Yali Hou,a Xiaoyu Ma,c Juanjuan Yang,c Haichao Han,b Jianlin Wu,b Longgang Jia,a Huimin Qin *ac and Fuping Lu *ab Aldonic acids are receiving increased interest due to their applications in nanotechnology, food, pharmaceutical and chemical industries. Microbes with aldose-oxidizing activity, rather than purified enzymes, are used for commercial production with limited success. Thus it is still very important to develop new processes using strains with more efficient and novel biocatalytic activities for the production of adonic acids. In the present study, Pseudomonas fragi TCCC11892 was found to be an efficient producer of aldonic acids, with the production of galactonic and L-rhamnonic acid by P. fragi reported for the first time. The semi-continuous production of maltobionic acid and lactobionic acid was Received 11th September 2018 À developed for P. fragi TCCC11892, achieving a yield of over 90 g L 1 for the first 7 cycles. The excellent Accepted 18th November 2018 performance of P. fragi in the production of lactobionic acid (119 g LÀ1) was also observed when using Creative Commons Attribution-NonCommercial 3.0 Unported Licence. DOI: 10.1039/c8ra07556e waste cheese whey as an inexpensive fermentation medium. Scaling up of the above process for rsc.li/rsc-advances production of aldonic acids with P. fragi TCCC11892 cells should facilitate their commercial applications. Introduction a workable approach to overcome the drawbacks associated with chemical or enzymatic oxidation.7–9 Many carbohydrate derivatives, such as sugar acids, are desir- Aldonic acids could be produced from microorganisms with able platform chemicals and have the potential to be used as aldose-oxidizing activity found in many archaea and bacteria a source of energy.1,2 Aldonic acids belong to the class of sugar and some eukaryotes.1,2,10 Recently, P.
    [Show full text]
  • 022434Orig1s000
    CENTER FOR DRUG EVALUATION AND RESEARCH APPLICATION NUMBER: 022434Orig1s000 PHARMACOLOGY REVIEW(S) DEPARTMENT OF HEALTH AND HUMAN SERVICES PUBLIC HEALTH SERVICE FOOD AND DRUG ADMINISTRATION CENTER FOR DRUG EVALUATION AND RESEARCH PHARMACOLOGY/TOXICOLOGY NDA REVIEW AND EVALUATION Application number: 22434 Supporting document/s: Electronic submission (SDN-001) Applicant’s letter date: January 12, 2011 CDER stamp date: January 12, 2011 Product: Argatroban Injection Indication: Prophylaxis or treatment of thrombosis in adult patients with heparin-induced thrombocytopenia; As an anticoagulant in adult patients with or at risk for heparin-induced thrombocytopenia undergoing percutaneous coronary intervention Applicant: Eagle Pharmaceuticals, Inc. Review Division: Division of Hematology Products Reviewer: Shwu-Luan Lee, Ph.D. Supervisor/Team Leader: Haleh Saber, Ph.D. Division Director: Ann Farrell, M.D. Project Manager: Lara Akinsanya Disclaimer Except as specifically identified, all data and information discussed below and necessary for approval of NDA 22434 are owned by Eagle Pharmaceuticals, Inc. or are data for which Eagle Pharmaceuticals, Inc. has obtained a written right of reference. Any information or data necessary for approval of NDA 22434 that Eagle Pharmaceuticals, Inc. does not own or have a written right to reference constitutes one of the following: (1) published literature, or (2) a prior FDA finding of safety or effectiveness for a listed drug, as described in the drug’s approved labeling. Any data or information described or referenced below from a previously approved application that Eagle Pharmaceuticals, Inc. does not own (or from FDA reviews or summaries of a previously approved application) is for descriptive purposes only and is not relied upon for approval of NDA 22434.
    [Show full text]
  • One-Pot Synthesis of Lactose Derivatives from Whey Permeate
    foods Article One-Pot Synthesis of Lactose Derivatives from Whey Permeate Maryam Enteshari and Sergio I. Martínez-Monteagudo * Dairy and Food Science Department, South Dakota State University, Alfred Dairy Science Hall, Brookings, SD 57007, USA; [email protected] * Correspondence: [email protected]; Tel.: +1-605-688-4118 Received: 17 May 2020; Accepted: 5 June 2020; Published: 13 June 2020 Abstract: The simultaneous production of lactulose (LAU), lactobionic acid (LBA), and organic acids from sweet and acid whey permeate (SWP and AWP) via catalytic synthesis (5% Ru/C) was studied in a continuous stirred-tank reactor. At selected conditions (60 ◦C, 60 bar, and 600 rpm), a maximum conversion of lactose (37 and 34%) was obtained after 90 min for SWP and AWP, respectively. The highest yield calculated with respect to the initial concentration of lactose for LAU was 22.98 0.81 ± and 15.29 0.81% after only 30 min for SWP, and AWP, respectively. For LBA, a maximum yield was ± found in SWP (5.23%) after 210 min, while about 2.2% was found in AWP. Six major organic acids (gluconic, pyruvic, lactic, formic, acetic, and citric acid) were quantified during the one-pot synthesis of lactose. Keywords: one-pot synthesis; catalysis; lactulose; lactobionic acid 1. Introduction Whey is the main byproduct obtained from the manufacture of cheese, yogurt, and milk protein concentrates [1]. It is the yellowish liquid separated from curds, and it is mainly made of water (~94%), lactose (~5%), proteins (~1%), minerals (~1%), and milk fat (~0.5%) [2]. As a byproduct, whey is concentrated and further fractionated to produce a wide array of products and ingredients with food and pharmaceutical applications.
    [Show full text]