DOCSLIB.ORG

A Novel Ninhydrin Reagent for Analysing

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
A Novel Ninhydrin Reagent for Analysing (19) TZZ ¥_T (11) EP 2 735 877 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: G01N 33/68 (2006.01) 08.03.2017 Bulletin 2017/10 (21) Application number: 13193944.9 (22) Date of filing: 21.11.2013 (54) A NOVEL NINHYDRIN REAGENT FOR ANALYSING NITROGEN-CONTAINING COMPOUNDS NEUARTIGES NINHYDRIN REAGENZ UND VERFAHREN ZUR VERWENDUNG DAVON NOUVEAU RÉACTIF NINHYDRINE ET SON PROCÉDÉ D’UTILISATION (84) Designated Contracting States: (56) References cited: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB WO-A1-2008/081959 CN-A- 102 618 621 GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO GB-A- 1 349 491 SU-A1- 1 597 700 PL PT RO RS SE SI SK SM TR US-A- 3 778 230 US-A- 4 274 833 (30) Priority: 21.11.2012 GB 201220902 • R. BHUSHAN ET AL: "Direct thin layer chromatography enantioresolution of some (43) Date of publication of application: basic dl-amino acids using a pharmaceutical 28.05.2014 Bulletin 2014/22 industry waste as chiral impregnating reagent", JOURNAL OF PHARMACEUTICAL AND (73) Proprietor: JPP Chromatography Limited BIOMEDICAL ANALYSIS, vol. 21, no. 6, 1 January Plymouth, Devon PL9 0DZ (GB) 2000 (2000-01-01), pages 1143-1147, XP055099046, ISSN: 0731-7085, DOI: (72) Inventors: 10.1016/S0731-7085(99)00203-4 • Pitts, Leslie John • DATABASE FSTA [Online] INTERNATIONAL Ivybridge, Devon PL21 9BX (GB) FOOD INFORMATION SERVICE (IFIS), • Pallot, Michael Gerard FRANkFURT-MAIN, DE; 1971, NAKANISHI T ET Wembury, Devon PL9 0DZ (GB) AL: "Enzymic studies on cheese ripening. III. • Jones, Philip Rapid finger-printing on a mixed thin layer for Plymouth, Devon PL3 5BN (GB) qualitative analysis of casein hydrolysate. (translated)", XP002719439, Database accession (74) Representative: Akers, Noel James no. FS-1972-07-P-1107 N.J. Akers & Co 63 Lemon Street Truro, Cornwall TR1 2PN (GB) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 735 877 B1 Printed by Jouve, 75001 PARIS (FR) 1 EP 2 735 877 B1 2 Description determined by the intensity of the coloured product de- tected in the photometer by way of absorbance at the [0001] The present invention relates to a novel reagent specified wavelength. Accordingly, this method may be for analysing nitrogen-containing compounds, for exam- used qualitatively and quantitatively to determine which ple amino acids and the like, and to a method for using 5 amino acids are present in a test sample and the relative the same. concentrations of each. [0002] Amino acids are the components from which [0005] The colour reaction between ninhydrin and the proteins are formed, which in turn play a key role in many amino acid or amine is very slow at room temperature. biological processes. In some cases the presence or ab- It is significantly faster at elevated temperatures, but still sence of a particular amino acid in an individual can se- 10 takes many minutes, even at a temperature of 130°C and riously affect their health. For example, an individual suf- above. To maintain good chromatographic performance fering from the genetic metabolic disorder phenylketonu- the colour reaction needs to take place in a time period rea cannot metabolise phenylalanine; the accumulation of around one minute or less. To achieve this, hydrindan- of which severely affects their brain development. Ac- tin, the reduced form of ninhydrin, was found to be re- cordingly, methods for detecting free amino acids or de- 15 quired for the ninhydrin reagent to be effective and pro- termining the amino acid compositions of proteins are vide an acceptable rate of reaction. There have been a vital for the proper diagnosis and management of diseas- number of suggested reasons or mechanisms for ex- es. Similarly, such methods are important for the analysis plaining the ability of hydrindantin to speed up the forma- of commercial drugs, food and foodstuffs, as well as pro- tion of the coloured products at elevated temperatures. tein and enzyme research and development. More gen- 20 One suggestion is that hydrindantin acts as a stabiliser erally, the detection and identification of nitrogen-con- for one of the reaction intermediates. As such it is con- taining compounds finds applications across a wide sidered as an accelerator not a catalyst. range of disciplines, including, agricultural, biochemical, [0006] The term ’ninhydrin reagent’ refers to a solution clinical, environmental, food, forensic, histochemical, or solutions containing all of the constituents necessary microbiological, medical, nutritional, plant and protein 25 for use in the amino acid analysers. Accordingly, a nin- sciences. hydrin reagent comprises hydrindantin, ninhydrin and the [0003] At present, free or hydrolytically released amino requisite buffers and solvents. The ninhydrin reagent acids are typically detected using automatic amino acid may be formed by adding a separate solution of hydrin- analysers. In the 1950’s the first automated amino acid dantin to the ninhydrin solution. Although, it would be analysis method was developed by Moore, Stein and 30 preferable provide one solution comprising all of the con- Spackman, (Spackman DH, Stein WH, and Moore S. Au- stituents necessary for amino acid analysis, an unaccept- tomatic recording apparatus for use in the chromatogra- ably low shelf life of the ninhydrin reagent would result. phy of amino acids. Anal Chem, 1958, 30:1190-1206). Alternatively, hydrindantin may be produced in situ by This multi-stage process involves separating the amino adding a reducing agent to the ninhydrin solution, thereby acids by ion exchange liquid chromatography. A ninhy- 35 reducing a portion of the ninhydrin to hydrindantin. The drin reagent is pumped from a reagent reservoir, mixed formation of hydrindantin in situ occurs more or less in- with the eluent from the ion exchange column and passed stantaneously in the presence of a strong reducing agent. through a steel or plastic reaction coil, heated to the tem- However, both of these methods require the user to mix perature required for reaction. Ninhydrin reacts with all a separate solution of ninhydrin with a separate solution amino acids and related amine compounds to form highly 40 of hydrindantin or a suitable reducing agent before the coloured reaction products. Ruhemann’s purple is ninhydrin reagent is ready to be used in the amino acid formed by primary amines and primary amino acids and analysis. may be measured by absorbance of light at a wavelength [0007] In recent times it has become the preferred of 570nm. Other coloured reaction products, in particular practice for manufacturers to provide two bottles, one yellow reaction products, are formed by secondary45 comprising a solution of hydrindantin in an organic sol- amines and a number of secondary amino acids. These vent and the other comprising a solution of ninhydrin, an reaction products may be measured by its absorbance aqueous buffer and an additional organic solvent, both of light at a wavelength of 440nm. The coloured reaction bottles being tightly sealed under an inert gas atmos- products vary in intensity according to the concentration phere. The contents of the bottles are then mixed to form of amino acid. 50 the ninhydrin reagent shortly before or immediately prior [0004] The amino acid reaction products are passed to use in an amino acid analyser. through a photometer where the light absorbed by the [0008] Unfortunately, hydrindantin is a very difficult re- dye complexes is detected at suitable wavelengths, in agent to handle. It is particularly unstable in the presence particular 570nm and 440nm. The presence of different of air, the oxygen rapidly oxidising the hydrindantin back amino acids may be determined by chromatography. The 55 to ninhydrin. Only relatively small amounts of air are nec- identity of each amino acid is established on the basis of essary to seriously deplete the hydrindantin and thus its migration characteristics and thus its position on the substantially reduce the sensitivity of the colour produc- chromatogram. The concentration of the amino acid is tion. If air is not rigidly excluded from the reagent, the 2 3 EP 2 735 877 B1 4 hydrindantin concentration will slowly drop until no colour agents have been assessed for their suitability for use in reaction will take place in the time frame of the chroma- reagents necessary for amino acid analysis Reducing tographic analysis. agents for ninhydrin are preferably highly soluble in the [0009] Exposure of a ninhydrin reagent comprising hy- reagent solution, have an excellent reducing property drindantin to the surrounding air must therefore be kept 5 against ninhydrin, do not form coloured by products, are to an absolute minimum as even minute traces of oxygen inert to the equipment, and are stable and easy to handle. exposure will cause a steady loss in hydrindantin activity. However, as is discussed in more detail below, existing An inert atmosphere, usually nitrogen, may be used both reducing agents do not exhibit all of these characteristics in the preparation and during use of the ninhydrin rea- and therefore interfere to a significant degree with the gent. As can be appreciated, this requirement results in 10 sensitivity and accuracy of amino acid analysis in one or the need for complex equipment and handling proce- more ways. dures, to ensure hydrindantin activity does not deterio- [0014] During the continuing development of the nin- rate at an unacceptable rate before and/or during its use.
Load more

Recommended publications
  • A Taxonomic Note on the Genus Lactobacillus
    Taxonomic Description template 1 A taxonomic note on the genus Lactobacillus: 2 Description of 23 novel genera, emended description 3 of the genus Lactobacillus Beijerinck 1901, and union 4 of Lactobacillaceae and Leuconostocaceae 5 Jinshui Zheng1, $, Stijn Wittouck2, $, Elisa Salvetti3, $, Charles M.A.P. Franz4, Hugh M.B. Harris5, Paola 6 Mattarelli6, Paul W. O’Toole5, Bruno Pot7, Peter Vandamme8, Jens Walter9, 10, Koichi Watanabe11, 12, 7 Sander Wuyts2, Giovanna E. Felis3, #*, Michael G. Gänzle9, 13#*, Sarah Lebeer2 # 8 '© [Jinshui Zheng, Stijn Wittouck, Elisa Salvetti, Charles M.A.P. Franz, Hugh M.B. Harris, Paola 9 Mattarelli, Paul W. O’Toole, Bruno Pot, Peter Vandamme, Jens Walter, Koichi Watanabe, Sander 10 Wuyts, Giovanna E. Felis, Michael G. Gänzle, Sarah Lebeer]. 11 The definitive peer reviewed, edited version of this article is published in International Journal of 12 Systematic and Evolutionary Microbiology, https://doi.org/10.1099/ijsem.0.004107 13 1Huazhong Agricultural University, State Key Laboratory of Agricultural Microbiology, Hubei Key 14 Laboratory of Agricultural Bioinformatics, Wuhan, Hubei, P.R. China. 15 2Research Group Environmental Ecology and Applied Microbiology, Department of Bioscience 16 Engineering, University of Antwerp, Antwerp, Belgium 17 3 Dept. of Biotechnology, University of Verona, Verona, Italy 18 4 Max Rubner‐Institut, Department of Microbiology and Biotechnology, Kiel, Germany 19 5 School of Microbiology & APC Microbiome Ireland, University College Cork, Co. Cork, Ireland 20 6 University of Bologna, Dept. of Agricultural and Food Sciences, Bologna, Italy 21 7 Research Group of Industrial Microbiology and Food Biotechnology (IMDO), Vrije Universiteit 22 Brussel, Brussels, Belgium 23 8 Laboratory of Microbiology, Department of Biochemistry and Microbiology, Ghent University, Ghent, 24 Belgium 25 9 Department of Agricultural, Food & Nutritional Science, University of Alberta, Edmonton, Canada 26 10 Department of Biological Sciences, University of Alberta, Edmonton, Canada 27 11 National Taiwan University, Dept.
    [Show full text]
  • A Taxonomic Note on the Genus Lactobacillus
    TAXONOMIC DESCRIPTION Zheng et al., Int. J. Syst. Evol. Microbiol. DOI 10.1099/ijsem.0.004107 A taxonomic note on the genus Lactobacillus: Description of 23 novel genera, emended description of the genus Lactobacillus Beijerinck 1901, and union of Lactobacillaceae and Leuconostocaceae Jinshui Zheng1†, Stijn Wittouck2†, Elisa Salvetti3†, Charles M.A.P. Franz4, Hugh M.B. Harris5, Paola Mattarelli6, Paul W. O’Toole5, Bruno Pot7, Peter Vandamme8, Jens Walter9,10, Koichi Watanabe11,12, Sander Wuyts2, Giovanna E. Felis3,*,†, Michael G. Gänzle9,13,*,† and Sarah Lebeer2† Abstract The genus Lactobacillus comprises 261 species (at March 2020) that are extremely diverse at phenotypic, ecological and gen- otypic levels. This study evaluated the taxonomy of Lactobacillaceae and Leuconostocaceae on the basis of whole genome sequences. Parameters that were evaluated included core genome phylogeny, (conserved) pairwise average amino acid identity, clade- specific signature genes, physiological criteria and the ecology of the organisms. Based on this polyphasic approach, we propose reclassification of the genus Lactobacillus into 25 genera including the emended genus Lactobacillus, which includes host- adapted organisms that have been referred to as the Lactobacillus delbrueckii group, Paralactobacillus and 23 novel genera for which the names Holzapfelia, Amylolactobacillus, Bombilactobacillus, Companilactobacillus, Lapidilactobacillus, Agrilactobacil- lus, Schleiferilactobacillus, Loigolactobacilus, Lacticaseibacillus, Latilactobacillus, Dellaglioa,
    [Show full text]
  • Impairment of Melibiose Utilization in Streptococcus Mutans Serotype C Gtfa Mutants
    University of Nebraska - Lincoln DigitalCommons@University of Nebraska - Lincoln Veterinary and Biomedical Sciences, Papers in Veterinary and Biomedical Science Department of March 1989 Impairment of Melibiose Utilization in Streptococcus mutans Serotype c gtfA Mutants Raul G. Barletta University of Nebraska - Lincoln, [email protected] Roy Curtiss III Washington University, St. Louis, Missouri Follow this and additional works at: https://digitalcommons.unl.edu/vetscipapers Part of the Veterinary Medicine Commons Barletta, Raul G. and Curtiss, Roy III, "Impairment of Melibiose Utilization in Streptococcus mutans Serotype c gtfA Mutants" (1989). Papers in Veterinary and Biomedical Science. 13. https://digitalcommons.unl.edu/vetscipapers/13 This Article is brought to you for free and open access by the Veterinary and Biomedical Sciences, Department of at DigitalCommons@University of Nebraska - Lincoln. It has been accepted for inclusion in Papers in Veterinary and Biomedical Science by an authorized administrator of DigitalCommons@University of Nebraska - Lincoln. INFECTION AND IMMUNITY, Mar. 1989, p. 992-995 Vol. 57, No. 3 0019-9567/89/030992-04$02.00/0 Copyright © 1989, American Society for Microbiology Impairment of Melibiose Utilization in Streptococcus mutans Serotype c gtfA Mutants RAUL G. BARLETTA' 2t AND ROY CURTISS II12* Department ofMicrobiology, University ofAlabama at Birmingham, Birmingham, Alabama 35294,' and Department ofBiology, Washington University, St. Louis, Missouri 631302 Received 16 September 1988/Accepted 21 November 1988 The Streptococcus mutans serotype c gtfA gene encodes a 55-kilodalton sucrose-hydrolyzing enzyme. Analysis of S. mutans gtfA mutants revealed that the mutant strains were specifically impaired in the ability to use melibiose as a sole carbon source. S.
    [Show full text]
  • Comparison of Sugar Profile Between Leaves and Fruits of Blueberry And
    plants Article Comparison of Sugar Profile between Leaves and Fruits of Blueberry and Strawberry Cultivars Grown in Organic and Integrated Production System Milica Fotiri´cAkši´c 1,*, Tomislav Tosti 2 , Milica Sredojevi´c 3 , Jasminka Milivojevi´c 1, Mekjell Meland 4 and Maja Nati´c 2 1 Faculty of Agriculture, University of Belgrade, 11080 Belgrade, Serbia 2 Faculty of Chemistry, University of Belgrade, 11158 Belgrade, Serbia 3 Innovation Center, Faculty of Chemistry, University of Belgrade, 11158 Belgrade, Serbia 4 Norwegian Institute of Bioeconomy Research-NIBIO Ullensvang, 5781 Lofthus, Norway * Correspondence: [email protected]; Tel.: +381642612710 Received: 13 May 2019; Accepted: 19 June 2019; Published: 4 July 2019 Abstract: The objective of this study was to determine and compare the sugar profile, distribution in fruits and leaves and sink-source relationship in three strawberry (‘Favette’, ‘Alba’ and ‘Clery’) and three blueberry cultivars (‘Bluecrop’, ‘Duke’ and ‘Nui’) grown in organic (OP) and integrated production systems (IP). Sugar analysis was done using high-performance anion-exchange chromatography (HPAEC) with pulsed amperometric detection (PAD). The results showed that monosaccharide glucose and fructose and disaccharide sucrose were the most important sugars in strawberry, while monosaccharide glucose, fructose, and galactose were the most important in blueberry. Source-sink relationship was different in strawberry compared to blueberry, having a much higher quantity of sugars in its fruits in relation to leaves. According to principal component analysis (PCA), galactose, arabinose, and melibiose were the most important sugars in separating the fruits of strawberries from blueberries, while panose, ribose, stachyose, galactose, maltose, rhamnose, and raffinose were the most important sugar component in leaves recognition.
    [Show full text]
  • Cheminformatics for Genome-Scale Metabolic Reconstructions
    CHEMINFORMATICS FOR GENOME-SCALE METABOLIC RECONSTRUCTIONS John W. May European Molecular Biology Laboratory European Bioinformatics Institute University of Cambridge Homerton College A thesis submitted for the degree of Doctor of Philosophy June 2014 Declaration This thesis is the result of my own work and includes nothing which is the outcome of work done in collaboration except where specifically indicated in the text. This dissertation is not substantially the same as any I have submitted for a degree, diploma or other qualification at any other university, and no part has already been, or is currently being submitted for any degree, diploma or other qualification. This dissertation does not exceed the specified length limit of 60,000 words as defined by the Biology Degree Committee. This dissertation has been typeset using LATEX in 11 pt Palatino, one and half spaced, according to the specifications defined by the Board of Graduate Studies and the Biology Degree Committee. June 2014 John W. May to Róisín Acknowledgements This work was carried out in the Cheminformatics and Metabolism Group at the European Bioinformatics Institute (EMBL-EBI). The project was fund- ed by Unilever, the Biotechnology and Biological Sciences Research Coun- cil [BB/I532153/1], and the European Molecular Biology Laboratory. I would like to thank my supervisor, Christoph Steinbeck for his guidance and providing intellectual freedom. I am also thankful to each member of my thesis advisory committee: Gordon James, Julio Saez-Rodriguez, Kiran Patil, and Gos Micklem who gave their time, advice, and guidance. I am thankful to all members of the Cheminformatics and Metabolism Group.
    [Show full text]
  • Coinciding with the Progress of Aggregation, Was Found to Be Particularly Dependent on the Concentration and the Temperature of the Solution
    VOL. 35, 1949 GENETICS: LINDEGREN AND L1NDEGREN 23 coinciding with the progress of aggregation, was found to be particularly dependent on the concentration and the temperature of the solution. Dur- ing the aggregation no increase in free sulfhydryl groups could be detected, and the protein did not seem to have its ability to crystallize impaired. * This work had the support of grants of the BACHE FUND of the NATIONAL ACADEMY OF SCIENCES and the Office of Naval Research. ** Communication No. 168. t Edsall16 has recently discussed the influence of the pH and ionic strength on the coefficient B of the proteins. $ Built.by Mr. W. H. Baker, Elmhurst, L. I., N. Y. § The sample was obtained through the courtesy of Mr. T. J. Deszczynski of the Department of Chemistry, Columbia University, New York, N. Y. 1 Svedberg, T., and Pedersen, K. O., The Ultracentrifuge, Oxford (1940), p. 382. 2 Svedberg, T., Nature, 128, 999 (1931). a Sjogren, B., and Svedberg, T., J. Am. Chem. Soc., 52, 5187 (1930). 4 Nord, F. F., Ranke-Abonyi, 0. M. v., and Weiss, G., Ber., 65, 1148 (1932); Ranke- Abonyi, 0. M. v., and Nord, F. F., Kolloid-Z., 58, 198 (1932); Weiss, G., and Nord, F. F., Z. physik. Chem., 166A, 1 (1933); Lange, F. E. M., and Nord, F. F., Biochem. Z., 278, 173 (1935); Holzapfel, L., Kolloid-Z., 85, 272 (1938); Bull, H. B., Z physik. Chem., 161A, 192 (1932). r Neduzhii, A. A., J. Applied Chem. (U.S.S.R.), 19, 535 (1946). 6 Putzeys, P., and Brosteaux, J., Trans.
    [Show full text]
  • International Food Research Journal 20(6): 3293-3298 (2013) Journal Homepage
    International Food Research Journal 20(6): 3293-3298 (2013) Journal homepage: http://www.ifrj.upm.edu.my Biochemical characterization and technological properties of predominant Lactobacilli isolated from East-Azarbaijan sourdoughs (Iran) 1*Golshan Tafti, A., 2Peighambardoust, S. H. and 3Hejazi, M. A. 1Department of Agricultural Engineering Research, Agricultural Research Centre, Kerman, I.R. Iran 2Department of Food Science, College of Agriculture, University of Tabriz, Tabriz 5166616471, I.R. Iran 3Branch for Northwest and West region, Agricultural Biotechnology Research Institute, Tabriz, Iran Article history Abstract Received: 1 March 2013 Seventeen traditional sourdough samples were collected from the Northern regions in East- Received in revised form: Azarbaijan province of Iran. The pH and total titratable acidity (TTA) values of the sourdoughs 31 July 2013 varied from 3.71-4.07 and 15.2-26.8 ml, respectively. A total of 50 Lactobacillus strains were Accepted: 9 July 2013 isolated from the sourdoughs and identified by biochemical methods. Of the isolates, 74% were identified asL. plantarum and L. curvatus or L. casei subsp. rhamnosus, 10% as L. morinus or L. Keywords paralimentarius and 4% as L. sake or L. bavaricus and L. casei subsp. Casei. Three isolates from the main groups were selected and identified using 16S rRNA gene sequencing. The results of Biochemical gene sequencing revealed the isolates as L. plantarum, L. curvatus and L. paralimentarius. All characterization three Lactobacillus strains produced exopolysaccharide from sucrose in MRS broth medium Lactobacillus and also showed proteolytic activity. Lactobacillus curvatus had weak proteolytic activity Sourdough compared to other strains. The strains showed some differences in acidification properties Technological properties both in MRS broth and sourdough fermentation.
    [Show full text]
  • Title Isomerization of Saccharides in Subcritical Aqueous Alcohols
    Isomerization of Saccharides in Subcritical Aqueous Alcohols( Title Dissertation_全文 ) Author(s) Gao, Da-Ming Citation 京都大学 Issue Date 2016-03-23 URL https://doi.org/10.14989/doctor.k19754 Right 許諾条件により本文は2016-10-01に公開 Type Thesis or Dissertation Textversion ETD Kyoto University Isomerization of Saccharides in Subcritical Aqueous Alcohols Da-Ming Gao 2016 Contents General Introduction ··········································································1 Chapter 1 Kinetics of Sucrose Hydrolysis in a Subcritical Water-ethanol Mixture 1.1. Introduction ·····················································································4 1.2. Materials and Methods ········································································4 1.3. Results and Discussion ········································································5 1.4. Conclusions ··················································································· 11 Chapter 2 Kinetic Analysis for the Isomerization of Glucose, Fructose, and Mannose in Subcritical Aqueous Ethanol 2.1. Introduction ···················································································12 2.2. Materials and Methods ······································································12 2.3. Results and Discussion ······································································13 2.4. Conclusions ···················································································20 Chapter 3 Promotion or Suppression of Glucose Isomerization in Subcritical Aqueous
    [Show full text]
  • Comparison of Melibiose and Trehalose As Stabilising Excipients for Spray-Dried Β-Galactosidase Formulations
    Accepted Manuscript Comparison of melibiose and trehalose as stabilising excipients for spray-dried β-galactosidase formulations Tiina Lipiäinen, Heikki Räikkönen, Anna-Maija Kolu, Marikki Peltoniemi, Anne Juppo PII: S0378-5173(18)30182-0 DOI: https://doi.org/10.1016/j.ijpharm.2018.03.035 Reference: IJP 17378 To appear in: International Journal of Pharmaceutics Received Date: 20 January 2018 Revised Date: 1 March 2018 Accepted Date: 17 March 2018 Please cite this article as: T. Lipiäinen, H. Räikkönen, A-M. Kolu, M. Peltoniemi, A. Juppo, Comparison of melibiose and trehalose as stabilising excipients for spray-dried β-galactosidase formulations, International Journal of Pharmaceutics (2018), doi: https://doi.org/10.1016/j.ijpharm.2018.03.035 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Title Comparison of melibiose and trehalose as stabilising excipients for spray-dried β-galactosidase formulations Authors 5 Tiina Lipiäinena, Heikki Räikkönena, Anna-Maija Kolua, Marikki Peltoniemia, Anne Juppoa a Division of Pharmaceutical Chemistry and Technology, Faculty of Pharmacy, University of Helsinki, Finland Corresponding author Tiina Lipiäinen 10 E-mail: [email protected] Postal address: Division of Pharmaceutical Chemistry and Technology Faculty of Pharmacy P.O. Box 56 (Viikinkaari 5 E) FI-00014 University of Helsinki 15 00790 Helsinki Finland Telephone: +358 2941 59346 1 Abstract 20 Spray-dried protein formulations commonly require stabilising excipients to prevent protein degradation during processing and storage, and trehalose has been commonly used.
    [Show full text]
  • Versatile Building Blocks from Disaccharides: Glycosylated 5-Hydroxymethylfurfuralsi Dierk Martin and Frieder W
    Tetrahedron: Asymmetry 17 (2006) 756–762 Versatile building blocks from disaccharides: glycosylated 5-hydroxymethylfurfuralsI Dierk Martin and Frieder W. Lichtenthaler* Clemens-Scho¨pf-Institut fu¨r Organische Chemie und Biochemie, Technische Universita¨t Darmstadt, Petersenstraße 22, D-64287 Darmstadt, Germany Received 10 December 2005; accepted 19 December 2005 Available online 15 March 2006 Dedicated to Professor Klaus Buchholz on the occasion of his 65th birthday Abstract—A practical protocol for the elaboration of O-glycosyl-HMF’s from glycosyl-(1!6)-glucoses is reported, the two steps involving aluminate-promoted isomerization to the respective 6-O-glycosyl-fructoses and subsequent selective dehydration of the fructose portion. Accordingly, melibiose, gentiobiose, and primeverose are converted into the corresponding 2-uloses and, then, into a-GalMF 11, b-GMF 12, and b-XylMF 13. Pt/C-catalyzed oxidation with oxygen in NaOH at 25 °C efficiently generated the respec- tive furoic acids from a-GalMF and a-GMF, whilst Pt/O2 in water at 50 °C also oxidizes the primary OH to give the dicarboxylic acids 15 and 17–key building blocks for the generation of novel types of polyesters and polyamides. Ó 2006 Elsevier Ltd. All rights reserved. 1. Introduction HO O As carbohydrates represent 75% of the annually renew- O HOOC O COOH H able biomass, their utilization for the generation of 1 2 chemicals and materials that eventually replace those from fossil resources is a major challenge for green 2,3 OH chemistry. This entails the development of efficient O methodologies for the simultaneous reduction of their HO oxygen content and introduction of C@C and C@O HO HO functionality toward industrially viable building blocks.
    [Show full text]
  • Present Status on Removal of Raff Inose Family Oligosaccharides – a Review
    Czech Journal of Food Sciences, 37, 2019 (3): 141–154 Review https://doi.org/10.17221/472/2016-CJFS Present status on removal of raff inose family oligosaccharides – a Review Jian Zhang*, Guangsen Song*, Yunjun Mei, Rui Li, Haiyan Zhang, Ye Liu School of Chemical and Environmental Engineering, Wuhan Polytechnic University, Wuhan, P.R. China *Corresponding authors: [email protected]; [email protected] Citation: Zhang J., Song G., Mei Y., Li R., Zhang H., Liu Y. (2019): Present status on removal of raffinose family oligosacchari- des ‒ a Review. Czech J. Food Sci., 37: 141–154. Abstract: Raffinose family oligosaccharides (RFOs) are α-galactosyl derivatives of sucrose or glucose. They are found in a large variety of seeds from many different families such as beans, vegetables and whole grains. Due to absence of α-galactosidase in the digestive tract of humans and other monogastric animals, RFOs are responsible for intestinal disturbances (flatulence) following the ingestion of legume-derived products. Structural relationships of RFOs and their enzymatic degradation mechanism are described. Concentration and distribution from various seed sources are introduced. The present status on removal of the RFOs (such as soaking, cooking, germination, and addition of α-galactosidase) is summarized. At the meantime, α-galactosidases from botanic and microbial sources and their partial enzymatic properties are also presented in detail. Based on a comparison of various removal treatments, the microbial α-galactosidases are thought as the most optimum
    [Show full text]
  • WO 2014/028243 Al 20 February 2014 (20.02.2014)
    (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 2014/028243 Al 20 February 2014 (20.02.2014) (51) International Patent Classification: DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, A23L 1/236 (2006.01) HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, (21) International Application Number: MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, PCT/US2013/053377 OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SC, (22) International Filing Date: SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, 2 August 2013 (02.08.2013) TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (26) Publication Language: English GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (30) Priority Data: UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, 61/682,456 13 August 2012 (13.08.2012) US TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, (71) Applicant: MCNEIL NUTRITIONALS, LLC [US/US]; MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, 601 Office Drive, Fort Washington, Pennsylvania 19034 TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, (US).
    [Show full text]