Skip to main content
Erschienen in: Cellulose 11/2017

19.08.2017 | Review Paper

Glucose, not cellobiose, is the repeating unit of cellulose and why that is important

verfasst von: Alfred D. French

Erschienen in: Cellulose | Ausgabe 11/2017

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

Despite nomenclature conventions of the International Union of Pure and Applied Chemistry and the International Union of Biochemistry and Molecular Biology, the repeating unit of cellulose is often said to be cellobiose instead of glucose. This review covers arguments regarding the repeating unit in cellulose molecules and crystals based on biosynthesis, shape, crystallographic symmetry, and linkage position. It is concluded that there is no good reason to disagree with the official nomenclature. Statements that cellobiose is the repeating unit add confusion and limit thinking on the range of possible shapes of cellulose. Other frequent flaws in drawings with cellobiose as the repeating unit include incorporation of O-1 as the linkage oxygen atom instead of O-4 (the O-1 hydroxyl is the leaving group in glycoside synthesis). Also, n often erroneously represents the number of cellobiose units when n should denote the degree of polymerization i.e., the number of glucose residues in the polysaccharide.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Literatur
Zurück zum Zitat Barber GA, Hassid WZ (1965) Synthesis of cellulose by enzyme preparations from the developing cotton boll. Nature 207:295–296CrossRef Barber GA, Hassid WZ (1965) Synthesis of cellulose by enzyme preparations from the developing cotton boll. Nature 207:295–296CrossRef
Zurück zum Zitat Barber GA, Elbein AD, Hassid WZ (1964) The synthesis of cellulose by enzyme systems from higher plants. J Biol Chem 239:4056–4061 Barber GA, Elbein AD, Hassid WZ (1964) The synthesis of cellulose by enzyme systems from higher plants. J Biol Chem 239:4056–4061
Zurück zum Zitat Cocinero EJ, Gamblin DP, Davis BG, Simons JP (2009) The building blocks of cellulose: the intrinsic conformational structures of cellobiose, its epimer, lactose, and their singly hydrated complexes. J Am Chem Soc 131:11117–11123CrossRef Cocinero EJ, Gamblin DP, Davis BG, Simons JP (2009) The building blocks of cellulose: the intrinsic conformational structures of cellobiose, its epimer, lactose, and their singly hydrated complexes. J Am Chem Soc 131:11117–11123CrossRef
Zurück zum Zitat Ernst A, Vasella A (1996) Oligosaccharide analogues of polysaccharides: part 8. Orthogonally protected cellobiose-derived dialkynes. A convenient method for the regioselective bromo- and protodegermylation of trimethylgermyl- and trimethylsilyl-protected dialkynes. Helv Chim Acta 79:1279–1294CrossRef Ernst A, Vasella A (1996) Oligosaccharide analogues of polysaccharides: part 8. Orthogonally protected cellobiose-derived dialkynes. A convenient method for the regioselective bromo- and protodegermylation of trimethylgermyl- and trimethylsilyl-protected dialkynes. Helv Chim Acta 79:1279–1294CrossRef
Zurück zum Zitat French AD (2011) Csonka GI (2011) Hydroxyl orientations in cellobiose and other polyhydroxyl compounds: modeling versus experiment. Cellulose 18:897–909CrossRef French AD (2011) Csonka GI (2011) Hydroxyl orientations in cellobiose and other polyhydroxyl compounds: modeling versus experiment. Cellulose 18:897–909CrossRef
Zurück zum Zitat French AD, Johnson GP (2004) What crystals of small analogs are trying to tell us about cellulose structure. Cellulose 11:5–22CrossRef French AD, Johnson GP (2004) What crystals of small analogs are trying to tell us about cellulose structure. Cellulose 11:5–22CrossRef
Zurück zum Zitat French AD, Johnson GP (2006) Quantum mechanics studies of cellobiose conformations. Can J Chem 84:603–612CrossRef French AD, Johnson GP (2006) Quantum mechanics studies of cellobiose conformations. Can J Chem 84:603–612CrossRef
Zurück zum Zitat French AD, Johnson GP (2007) Linkage and pyranosyl ring twisting in cyclodextrins. Carbohydr Res 342:1223–1237CrossRef French AD, Johnson GP (2007) Linkage and pyranosyl ring twisting in cyclodextrins. Carbohydr Res 342:1223–1237CrossRef
Zurück zum Zitat French AD, Johnson GP, Cramer CJ, Csonka GI (2012) Conformational analysis of cellobiose by electronic structure theories. Carbohydr Res 350:68–76CrossRef French AD, Johnson GP, Cramer CJ, Csonka GI (2012) Conformational analysis of cellobiose by electronic structure theories. Carbohydr Res 350:68–76CrossRef
Zurück zum Zitat Glaser L (1957) The enzymic synthesis of cellulose by Acetobacter xylinum. Biochim Biophys Acta 25:436 (single page note) CrossRef Glaser L (1957) The enzymic synthesis of cellulose by Acetobacter xylinum. Biochim Biophys Acta 25:436 (single page note) CrossRef
Zurück zum Zitat Glasser WG, Atalla RH, Blackwell J, Brown RM Jr, Burchard W, French AD, Klemm DO, Nishiyama Y (2012) About the structure of cellulose: debating the Lindman hypothesis. Cellulose 19:589–598CrossRef Glasser WG, Atalla RH, Blackwell J, Brown RM Jr, Burchard W, French AD, Klemm DO, Nishiyama Y (2012) About the structure of cellulose: debating the Lindman hypothesis. Cellulose 19:589–598CrossRef
Zurück zum Zitat Kalenius E, Kekäläinen T, Neitola R, Beyeh K, Rissanen K, Vainiotalo P (2008) Size- and structure-selective noncovalent recognition of saccharides by tetraethyl and tetraphenyl resorcinarenes in the gas phase. Chem Eur J 14:5220–5228CrossRef Kalenius E, Kekäläinen T, Neitola R, Beyeh K, Rissanen K, Vainiotalo P (2008) Size- and structure-selective noncovalent recognition of saccharides by tetraethyl and tetraphenyl resorcinarenes in the gas phase. Chem Eur J 14:5220–5228CrossRef
Zurück zum Zitat Kouwijzer MLCE, van Euck BP, Kooijman H, Kroon J (1995) An extension of the GROMOS force field for carbohydrates, resulting in improvement of the crystal structure determination of α-d-galactose. Acta Crystalloogr Sect B 51:209–220CrossRef Kouwijzer MLCE, van Euck BP, Kooijman H, Kroon J (1995) An extension of the GROMOS force field for carbohydrates, resulting in improvement of the crystal structure determination of α-d-galactose. Acta Crystalloogr Sect B 51:209–220CrossRef
Zurück zum Zitat Langan P, Nishiyama Y, Chanzy H (2001) X-ray structure of mercerized cellulose II at 1 Å resolution. Biomacromol 2:410–416CrossRef Langan P, Nishiyama Y, Chanzy H (2001) X-ray structure of mercerized cellulose II at 1 Å resolution. Biomacromol 2:410–416CrossRef
Zurück zum Zitat Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood PA (2008) Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures. J Appl Cryst 41:466–470CrossRef Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood PA (2008) Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures. J Appl Cryst 41:466–470CrossRef
Zurück zum Zitat Meader D, Atkins EDT, Happey F (1978) Cellulose trinitrate: molecular conformation and packing considerations. Polymer 19:1371–1374CrossRef Meader D, Atkins EDT, Happey F (1978) Cellulose trinitrate: molecular conformation and packing considerations. Polymer 19:1371–1374CrossRef
Zurück zum Zitat Medronho B, Romano A, Miguel MG, Stigsson L, Lindman B (2012) Rationalizing cellulose (in)solubility: reviewing basic physicochemical aspects and role of hydrophobic interactions. Cellulose 19:581–587CrossRef Medronho B, Romano A, Miguel MG, Stigsson L, Lindman B (2012) Rationalizing cellulose (in)solubility: reviewing basic physicochemical aspects and role of hydrophobic interactions. Cellulose 19:581–587CrossRef
Zurück zum Zitat Nishiyama Y, Langan P, Chanzy H (2002) Crystal structure and hydrogen-bonding system in cellulose Iβ from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc 124:9074–9082CrossRef Nishiyama Y, Langan P, Chanzy H (2002) Crystal structure and hydrogen-bonding system in cellulose Iβ from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc 124:9074–9082CrossRef
Zurück zum Zitat Nishiyama Y, Sugiyama J, Chanzy H, Langan P (2003) Crystal structure and hydrogen bonding system in cellulose Iα from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc 125:14300–14306CrossRef Nishiyama Y, Sugiyama J, Chanzy H, Langan P (2003) Crystal structure and hydrogen bonding system in cellulose Iα from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc 125:14300–14306CrossRef
Zurück zum Zitat Oscarson S (1999) Conjugation of monosaccharides – synthesis of glycosidic linkages in glycosides, oligosaccharides, and polysaccharides. In: Finch P (ed) Carbohydrates Structures, syntheses and dynamics. Kluwer Academic Publishers, Dordrecht Oscarson S (1999) Conjugation of monosaccharides – synthesis of glycosidic linkages in glycosides, oligosaccharides, and polysaccharides. In: Finch P (ed) Carbohydrates Structures, syntheses and dynamics. Kluwer Academic Publishers, Dordrecht
Zurück zum Zitat Strati GL, Willett JL, Momany FA (2002) Ab initio computational study of β-cellobiose conformers using B3LYP/6-311 ++G**. Carbohydr Res 337:1833–1849CrossRef Strati GL, Willett JL, Momany FA (2002) Ab initio computational study of β-cellobiose conformers using B3LYP/6-311 ++G**. Carbohydr Res 337:1833–1849CrossRef
Zurück zum Zitat Wada M, Chanzy H, Nishiyama Y, Langan P (2004) Cellulose IIII Crystal Structure and Hydrogen Bonding by Synchrotron X-ray and Neutron Fiber Diffraction. Macromolecules 37:8548–8555CrossRef Wada M, Chanzy H, Nishiyama Y, Langan P (2004) Cellulose IIII Crystal Structure and Hydrogen Bonding by Synchrotron X-ray and Neutron Fiber Diffraction. Macromolecules 37:8548–8555CrossRef
Zurück zum Zitat Wada M, Heux L, Nishiyama Y, Langan P (2009) X-ray crystallographic, scanning microprobe X-ray diffraction, and cross-polarized/magic angle spinning 13C NMR studies of the structure of cellulose IIIII. Biomacromol 10:302–309CrossRef Wada M, Heux L, Nishiyama Y, Langan P (2009) X-ray crystallographic, scanning microprobe X-ray diffraction, and cross-polarized/magic angle spinning 13C NMR studies of the structure of cellulose IIIII. Biomacromol 10:302–309CrossRef
Zurück zum Zitat Whitaker PM, Nieduszynski IA, Atkins EDT (1974) Structural aspects of soda-cellulose II. Polymer 15:125–127CrossRef Whitaker PM, Nieduszynski IA, Atkins EDT (1974) Structural aspects of soda-cellulose II. Polymer 15:125–127CrossRef
Metadaten
Titel
Glucose, not cellobiose, is the repeating unit of cellulose and why that is important
verfasst von
Alfred D. French
Publikationsdatum
19.08.2017
Verlag
Springer Netherlands
Erschienen in
Cellulose / Ausgabe 11/2017
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI
https://doi.org/10.1007/s10570-017-1450-3

Weitere Artikel der Ausgabe 11/2017

Cellulose 11/2017 Zur Ausgabe