Cellobiose

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Structural formula
Structure of Cellobiose
General
Surname Cellobiose
other names
  • Cellosis
  • 4- O- β- D -glucopyranosyl- D -glucose
  • D -glycosyl-β- (1 → 4) - D -glucose
Molecular formula C 12 H 22 O 11
Brief description

tasteless, odorless and colorless solid

External identifiers / databases
CAS number 528-50-7
EC number 208-436-5
ECHA InfoCard 100.007.670
PubChem 439178
ChemSpider 388323
DrugBank DB02061
Wikidata Q409017
properties
Molar mass 342.3 g mol −1
Physical state

firmly

density

0.6 g cm −3 (bulk density)

Melting point

239 ° C (decomposition)

solubility

readily soluble in water (111 g l −1 at 15 ° C)

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cellobiose is a naturally occurring disaccharide , which consists of two β-1,4- glycosidically linked glucose molecules .

Properties and occurrence

Cellobiose has been found to decay naturally in the endosperm of maize ( Zea mays ), in the needles of pine ( Pinus ) and in honey. In processed foods, cellobiose has been identified as a reversion product in hydrolyzed starch syrups.

Another development path is the natural decay of cellulose, for example during the decomposition process of wood by naturally occurring fungal enzymes. Most bacteria , fungi and higher living organisms, however, are unable to break down cellobiose into glucose subunits due to a lack of enzymes; only a few protozoa and fungi such as Aspergillus - , Penicillium - and Fusarium TYPES possess the necessary β-1,4-glucosidase or Cellobiases . Some wood- decomposing fungi such as Ceriporiopsis subvermispora can also oxidatively break down cellobiose via cellobiose dehydrogenase ( CDH ), an extracellular hemoflavoenzyme . This creates gluconic acid instead of glucose .

Manufacturing

Biotechnological production

The biotechnological production of cellobiose can be carried out by enzymatic hydrolysis of cellulose or by means of enzymatic processes e.g. B. can be realized technically from sucrose. The latter takes place in the presence of phosphate, with a phosphorylation of sucrose to glucose-1-phosphate (G-1-P) and fructose by sucrose phosphorylase (EC 2.4.1.7) being catalyzed. The fructose produced can be inverted to glucose in a second reaction by glucose isomerase (EC 5.3.1.5). The G-1-P present from the first reaction and the glucose produced in the second reaction are catalyzed in the third reaction by cellobiose phosphorylase (EC 2.4.1.20) with the release of phosphate to cellobiose.

Biotechnological production of cellobiose from sucrose through the use of sucrose phosphorylase, glucose isomerase and cellobiose phosphorylase

In the aqueous saccharide solution, in addition to the main disaccharide compound cellobiose, the monosaccharides glucose and fructose as well as other residues of phosphate, G-1-P and salts are present. The saccharide solution is desalinated by means of electrodialysis. By subsequent crystallization, followed by physical separation (e.g. centrifugation), the cellobiose can be obtained from multicomponent saccharide solutions with purities of over 99.5%.

Hydrolysis without enzymes

Cellobiose can be split into two glucose units by chemical means in acidic, neutral and alkaline aqueous solutions. The necessary activation energies differ only slightly, while the necessary temperatures differ greatly. The easiest way is acid hydrolysis with hydrochloric acid , dilute sulfuric or phosphoric acid - starting at 18 ° C; at least 60 ° C are required for alkaline cleavage, and even 180 ° C for hydrothermal degradation.

Activation energies for hydrolysis without enzymes
Hydrolysis type necessary temp.
in ° C 		Activation energy
in kJ / mol
angry 18-99.5 125.4
alkaline 60-80 ≈ 120
neutral 180-249 136

Treatment of cellulose with acetic acid or acetic anhydride results in the poorly water-soluble cellobiose octaacetate (acetic acid ester ).

use

The use of cellulose from any plant fibers for the production of glucose and from it flammable lower alcohols (such as butanols ) is opposed by the fact that very many easy-to-obtain cellulases (mostly from the tubular fungi Trichoderma viride and T. reesei ) cannot break down cellobiose. This is why β-1,4-glucosidase ( Novozym ) obtained from Aspergillus niger is added in test facilities .

Evidence and determination

Cellobiose can be detected by enzymatic cleavage with β-glucosidases and subsequent paper chromatographic detection of the cleavage product glucose. Chromatographic processes are established in instrumental analysis for the clear detection and quantitative determination of cellobiose. Thus, after derivatization with, for example, silylation reagents, cellobiose can be converted into volatile compounds, which in turn can be unequivocally identified and reliably quantified in various matrices by means of gas chromatography in the presence of other sugar compounds.

HPAEC-PAD chromatogram of a saccharide mixture using a NaOH (0.008-0.2 mol / l) gradient program - cellobiose elutes with a retention time of 47.02 min

In addition, the process of high-performance anion exchange chromatography in conjunction with pulsed amperometric detection (HPAEC-PAD) can be used very well, which deprotonates the saccharides under strongly alkaline chromatography conditions, so that they act as a stationary phase on a strong anion exchanger depending on their molecular structure be retarded to different degrees. The cellobiose is separated from other mono-, di- or other oligosaccharides present without previous derivatization reactions, so that a qualitative and quantitative determination can be carried out reliably.

Cellobiose can be detected wet-chemically through the formation of a red dye in the Wöhlk reaction , in Fearon's test and in the 1,6-diaminohexane method, although other 1,4-linked disaccharides such as e.g. B. lactose or maltose must be excluded, as they react in the same way.

Web links

Commons : Cellobiose  - collection of images, videos and audio files

Individual evidence

  1. ↑ a b Data sheet cellobiose (PDF) from Merck , accessed on December 14, 2010.
  2. ↑ a b c Data sheet D - (+) - Cellobiose, for microbiology, ≥99.0% from Sigma-Aldrich , accessed on December 1, 2019 ( PDF ).
  3. ↑ Entry on cellobiose in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ↑ Josef Schormüller: Textbook of food chemistry . Springer Verlag, 1961, p. 161 .
  5. ^ E. Gentinetta, M. Zambello, F. Salamini: Free sugar in developing maize grain . In: Cereal Chemistry . tape 56 , no. 2 , p. 81-83 .
  6. ^ BO Fraser-Reid, K. Tatsuta, J. Thiem: Glycoscience: Chemistry and Chemical Biology I-III . Springer Verlag, 2001, ISBN 3-540-67764-X , p. 1441 .
  7. ↑ Omotayo O. Erejuwa, Siti A. Sulaiman, Mohd S. Ab Wahab: Honey - A Novel Antidiabetic Agent . In: International Journal of Biological Sciences . tape 8 , no. 6 , p. 913-934 .
  8. ↑ Jose M. Alvarez-Suarez, Francesca Giampieri, Maurizio Battino: Honey as a source of dietary antioxidants: structures, bioavailability and evidence of protective effects against human chronic diseases . In: Current Medicinal Chemistry . tape 20 , no. 5 , 2013, p. 621-638 .
  9. ↑ A. Thompson, K. Anno, ML Wolfrom, M. Inatome: Acid Reversion Products from D-Glucose . In: Journal of the American Chemical Society . tape 76 , no. 5 , 1954, pp. 1309-1311 .
  10. ↑ Sabine M. Bergler: Transglycosidation products during the inversion of sucrose . In: Technische Universität Berlin / Institute for Food Technology and Food Chemistry (Ed.): Scientific thesis . Berlin, S. 17 .
  11. ↑ a b Martin Weidenbörner: Lexicon of food mycology . Springer-Verlag, Berlin / Heidelberg 2000, ISBN 3-540-65241-8 , pp. 34 .
  12. ↑ R. Erdmann: Biochemistry / Microbiology. Internship script from the Ruhr University Bochum .
  13. ↑ E. Duenhofen: Fermentation, purification and characterization of cellobiose dehydrogenase from Ceriporiopsis subvermispora. Diploma thesis at the University of Natural Resources and Life Sciences, Vienna , 2005.
  14. ↑ Ching-Tsang Hou, Jei-Fu Shaw: Biocatalysis and Biotechnology for Functional Foods and Industrial Products . Ed .: CRC press. 2007, ISBN 0-8493-9282-9 .
  15. ↑ M. Makina: Technology for the production of crystalline dextrose and fructose . In: Sugar Industry . tape 129 , no. 4 , 2004, p. 238-239 .
  16. ↑ S. Ouiazzane, B.Messnaoui, p Abderafi, J. Wouters, T. Bounahmidi: Modeling of sucrose crystallization kinetics: The influence of glucose and fructose . In: Journal of Crystal Growth . tape 310 , no. 15 , 2008, p. 3498-3503 .
  17. ↑ Marcel Lesch: Development of a crystallization process to obtain a disaccharide from multi-component saccharide solutions . In: Hochschule Niederrhein / Department of Nutrition (Ed.): Master Thesis . Mönchengladbach 2015, p. 88 .
  18. ^ A b S. Dumitriu: Polysaccharides: Structural Diversity and Functional Versatility. P. 906, CRC Press, 2004, ISBN 978-0-8247-5480-8 .
  19. ↑ B. Rodriguez, P. Dueritas, A. El-Hadj, R. Requena: The Influence of pH on the Hydrolysis of Cellobiose with β-1,4-Glucosidases from Aspergillus Niger. In: 1st World Conference on Biomass for Energy and Industry: Proceedings of the Conference Held in Sevilla , Spain, 5-9 June 2000, Earthscan, 2001, ISBN 978-1-902916-15-6 .
  20. ↑ H. Reznik: About the histochemical evidence of the β-glucosidases involved in lignification . In: Planta . tape 45 , no. 5 , 1955, pp. 455-469 , doi : 10.1007 / BF01937867 .
  21. ↑ I. Boldizsár, K. Horváth, G. Szedlay, I. Molnár-Perl: Simultaneous GC-MS quantitation of acids and sugars in the hydrolyzates of immunostimulant, water-soluble polysaccharides of basidiomycetes . In: Chromatographia . tape 47 , no. 2 , 1998, p. 413-419 .
  22. ^ I. Molnár-Perl, K. Horváth: Simultaneous quantitation of mono-, di- and trisaccharides as their TMS ether oxime derivatives by GC-MS: I. In model solutions . In: Chromatographia . tape 45 , no. 1 , 1997, p. 321-327 .
  23. ↑ Tim Wichmann: Development of an HPLC multi-method for the determination of mono-, di-, tri- and tetrasaccharides . In: Aachen University of Applied Sciences (ed.): Bachelor thesis . Jülich 2012, p. 12-29 .
  24. ↑ Klaus Ruppersberg, Stefanie Herzog, Manfred W. Kussler, Ilka Parchmann: How to visualize the different lactose content of dairy products by Fearon's test and Woehlk test in classroom experiments and a new approach to the mechanisms and formulas of the mysterious red dyes . In: Chemistry Teacher International . tape 0 , no. 0 17 October 2019 ISSN  2569-3263 , doi : 10.1515 / cti-2019-0008 ( degruyter.com [accessed on March 9, 2020]).