Cellulose as polymer of β-D-glucose

Cellulose in 3D

Cellulose (C₆H₁₀O₅)_n is a polysaccharide of beta-glucose.^[1][2] It forms the primary structural component of green plants. The primary cell wall of green plants is made of cellulose; the secondary wall contains cellulose with variable amounts of lignin. Lignin and cellulose, considered together, are termed lignocellulose, which (as wood) is argued to be one of the most common biopolymers on Earth (chrysolaminarin is often argued to be the other). Only one group of animals, the tunicates, has the ability to create and use cellulose. Some acetic acid bacteria are also known to synthesize cellulose, as well as many forms of algae, and the oomycetes. Image File history File links Download high resolution version (1100x488, 44 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Cellulose ... Image File history File links Download high resolution version (1100x488, 44 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Cellulose ... Image File history File links Download high-resolution version (1000x570, 211 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Cellulose ... Image File history File links Download high-resolution version (1000x570, 211 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Cellulose ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... Polysaccharides (sometimes called glycans) are relatively complex carbohydrates. ... Glucose (Glc), a monosaccharide (or simple sugar), is the most important carbohydrate in biology. ... Divisions Green algae Chlorophyta Charophyta Land plants (embryophytes) Non-vascular plants (bryophytes) Marchantiophyta—liverworts Anthocerotophyta—hornworts Bryophyta—mosses Vascular plants (tracheophytes) †Rhyniophyta—rhyniophytes †Zosterophyllophyta—zosterophylls Lycopodiophyta—clubmosses †Trimerophytophyta—trimerophytes Pteridophyta—ferns and horsetails Seed plants (spermatophytes) †Pteridospermatophyta—seed ferns Pinophyta—conifers Cycadophyta—cycads Ginkgophyta—ginkgo Gnetophyta—gnetae Magnoliophyta—flowering plants... Lignin (sometimes lignen) is a chemical compound that is most commonly derived from wood and is an integral part of the cell walls of plants, especially in tracheids, xylem fibres and sclereids. ... Trunks A tree trunk as found at the Veluwe, The Netherlands Wood is a solid material derived from woody plants, notably trees but also shrubs. ... This article or section does not adequately cite its references or sources. ... Adjectives: Terrestrial, Terran, Telluric, Tellurian, Earthly Atmosphere Surface pressure: 101. ... Chrysolaminarin (also known as leucosin) is a polymer of glucopyranoside units. ... Classes Ascidiacea Thaliacea Appendicularia Urochordata (sometimes known as tunicata and commonly called urochordates, tunicates or sea squirts) is the subphylum of saclike filter feeders with input and output siphons. ... Genera Acetobacter Acidicaldus Acidiphilium Acidisphaera Acidocella Acidomonas Asaia Belnapia Craurococcus Gluconacetobacter Gluconobacter Kozakia Leahibacter Muricoccus Neoasaia Oleomonas Paracraurococcus Rhodopila Roseococcus Rubritepida Saccharibacter Stella Swaminathania Teichococcus Zavarzinia Acetic acid bacteria are bacteria that derive their energy from the oxidation of ethanol to acetic acid during respiration. ... A seaweed (Laurencia) up close: the branches are multicellular and only about 1 mm thick. ... Orders Lagenidiales Leptomitales Peronosporales Pythiales Rhipidiales Saprolegniales Sclerosporales Water moulds or Oomycetes are a group of filamentous protists, physically resembling fungi. ...

Background

Cellulose is a common material in plant cell walls. It was discovered and isolated in the mid-nineteenth century by the French chemist Anselme Payen ("Cellulose. Structure, modification and hydrolysis", 1986). It occurs naturally in almost pure form in cotton fiber. In combination with lignin and hemicellulose, it is found in all plant material. Cellulose is the most abundant form of living terrestrial biomass^[1] with an estimated annual production of 1.5x10¹² Tonnes.^[3] (Note: This figure appears to be in error. It is seven times larger than the total Net Primary Production for the planet. The reference does not appear to have anything to do with the figure quoted for net annual production.) A cell wall is a fairly rigid layer surrounding a cell, located external to the cell membrane, that provides the cell with structural support, protection, and a filtering mechanism. ... Cotton ready for harvest. ... Lignin (sometimes lignen) is a chemical compound that is most commonly derived from wood and is an integral part of the cell walls of plants, especially in tracheids, xylem fibres and sclereids. ... A hemicellulose can be any of several heteropolymers (matrix polysaccharides) present in almost all cell walls along with cellulose. ... A tonne or metric ton (symbol t), sometimes referred to as a metric tonne, is a measurement of mass equal to 1,000 kilograms. ...

Some animals, particularly ruminants and termites, can digest cellulose with the help of symbiotic micro-organisms - see methanogen. Cellulose is not digestible by humans, and is often referred to as 'dietary fiber' or 'roughage', acting as a hydrophilic bulking agent for faeces. This article does not adequately cite its references or sources. ... Families Mastotermitidae Kalotermitidae Termopsidae Hodotermitidae Rhinotermitidae Serritermitidae Termitidae Termites, sometimes known as white ants, are a group of eusocial insects usually classified at the taxonomic rank of order, Isoptera. ... Meat Ants harvest Leaf Hoppers for their honey dew. ... Methanogens are archaea that produce methane as a metabolic byproduct. ... This article or section does not cite any references or sources. ... Trinomial name Homo sapiens sapiens Linnaeus, 1758 Humans, or human beings, are bipedal primates belonging to the mammalian species Homo sapiens (Latin: wise man or knowing man) in the family Hominidae (the great apes). ... Rabbit feces are usually 0. ...

Cellulose is the major constituent of paper and textiles made of cotton, linen and other plant fibers; further chemical processing can be performed to make cellophane, Clear rolling papers made from Viscose film, rayon, and more recently Cellulose has been found to make Modal, a textile derived from beechwood cellulose. Cellulose is used within the laboratory as a solid-state substrate for thin layer chromatography, and cotton linters, is used in the manufacture of nitrocellulose, historically used in smokeless gunpowder. A blank sheet of paper Paper is a commodity of thin material produced by the amalgamation of fibers, typically vegetable fibers composed of cellulose, which are subsequently held together by hydrogen bonding. ... Cellophane is a thin, transparent sheet made of processed cellulose. ... Viscose is a viscous organic liquid used to make rayon and cellophane. ... Rayon is a manufactured regenerated cellulosic fiber. ... Modal® is a bio-based fiber made by spinning reconstituted cellulose from beech trees. ... Pictured is a sophisticated gas chromatography system. ... For other uses, see Cotton (disambiguation). ... Skeletal formula of nitrocellulose Ball-and-stick model of a section of nitrocellulose Nitrocellulose (also: cellulose nitrate, flash paper) is a highly flammable compound formed by nitrating cellulose through, for example, exposure to nitric acid or another powerful nitrating agent. ... Smokeless powder Smokeless powder is the name given to a number of gunpowder-like propellants used in firearms which produce negligible smoke when fired, unlike the older black powder which it replaced. ...

Rayon is a very important fiber made out of cellulose and has been used for textiles since the beginning of the 20th century. Rayon is a manufactured regenerated cellulosic fiber. ...

Cellulose source and energy crops

Main article: Energy crop

Switchgrass is used as cellulose energy crop. An energy crop is a non-edible plant domesticated for use in agriculture, considered as a group (e. ... Binomial name Panicum virgatum L. Switchgrass (Panicum virgatum) is a warm season grass and is one of the dominant species of the central North American tallgrass prairie. ...

Chemistry

Cellulose monomers (β-glucose) are linked together through β(1→4)-glycosidic bonds by condensation. This is in contrast to the α(1→4)-glycosidic bonds present in other carbohydrates like starch. Cellulose is a straight chain polymer: unlike starch, no coiling occurs, and the molecule adopts an extended rod-like conformation. In microfibrils, the multiple hydroxyl groups on the glucose residues hydrogen bond with each other, holding the chains firmly together and contributing to their high tensile strength. This strength is important in cell walls, where they are meshed into a carbohydrate matrix, helping keep plant cells rigid. In chemistry, a monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer. ... In chemistry, a glycosidic bond is a certain type of functional group that joins a carbohydrate (sugar) molecule to an alcohol, which may be another carbohydrate. ... A condensation reaction is a chemical reaction in which two molecules or moieties combine to form one single molecule, together with the loss of a small molecule. ... In chemistry, a glycosidic bond is a certain type of functional group that joins a carbohydrate (sugar) molecule to an alcohol, which may be another carbohydrate. ... Starch (CAS# 9005-25-8) is a complex carbohydrate which is soluble in water; it is used by plants as a way to store excess glucose. ... An example of a quadruple hydrogen bond between a self-assembled dimer complex reported by Meijer and coworkers. ...

In contrast to starch, cellulose is also much more crystalline. Whereas starch has a crystalline to amorphous transition at 60 -70 °C in water as in cooking, it takes 320°C and 25 MPa for cellulose to become amorphous in water.^[3] Starch (CAS# 9005-25-8) is a complex carbohydrate which is soluble in water; it is used by plants as a way to store excess glucose. ... Crystallinity is the degree of structural order in a solid, often represented by a fraction or percentage. ... MPA is a TLA (three-letter acronym) that may mean: Macedonian Press Agency Marine Protected Area Maritime Patrol Aircraft Maryland and Pennsylvania Railroad (AAR reporting mark MPA) Master of Public Administration Master of Public Affairs Max Planck Institute for Astrophysics Metropolitan Police Authority Mid-atlantic Pagan Alliance Motion Picture Association...

Given a cellulose material, the portion that does not dissolve in a 17.5% solution of sodium hydroxide at 20 °C is α cellulose, which is true cellulose; the portion that dissolves and then precipitates upon acidification is β cellulose; and the proportion that dissolves but does not precipitate is γ cellulose.

Cellulose can be assayed using a method described by Updegraff in 1969, where the fiber is dissolved in acetic and nitric acid, and allowed to react with anthrone in sulfuric acid. The resulting coloured compound is assayed spectrophotometrically at a wavelength of approximately 635 nm. For the Stargate SG-1 episode, see 1969 (Stargate SG-1). ... Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. ... The chemical compound nitric acid (HNO3), also known as aqua fortis and spirit of nitre, is an aqueous solution of hydrogen nitrate (anhydrous nitric acid). ... Anthrone is a tricyclic aromatic hydrocarbon. ... Sulfuric acid, H2SO4, is a strong mineral acid. ... To help compare different orders of magnitudes this page lists lengths between 10-9 m (metre) and 10-8 m (1 nm and 10 nm). ...

Biosynthesis

In higher plants cellulose is synthesized at the plasma membrane by rosette terminal complexes (RTCs). The RTCs are hexameric protein structures, approximately 25 nm in diameter, that contain the cellulose synthase enzymes that synthesise the individual cellulose chains.^[4] The RTCs contain at least three different cellulose synthases, encoded by CesA genes, in an unknown stoichiometry.^[5] Separate sets of CesA genes are involved in primary and secondary cell wall biosynthesis. Cellulose synthase utilizes UDP-D-glucose precursors to generate microcrystalline cellulose. Cellulose synthesis requires chain initiation and elongation, and the two processes are separate. CesA glucosyltransferase initiates cellulose polymerization using a steroid primer, 'sitosterol-beta-glucoside' and UDP-glucose.^[6] A cellulase may function to cleave the primer from the mature chain. Drawing of a cell membrane A component of every biological cell, the cell membrane (or plasma membrane) is a thin and structured bilayer of phospholipid and protein molecules that envelopes the cell. ... A cell wall is a fairly rigid layer surrounding a cell, located external to the cell membrane, that provides the cell with structural support, protection, and a filtering mechanism. ...

Breakdown (cellulolysis)

Cellulolysis is the process relating to or causing the hydrolysis of cellulose (i.e. cellulolytic bacteria, fungi or enzymes). Hydrolysis is a chemical reaction or process in which a chemical compound reacts with water. ...

Mammals do not have the ability to break down cellulose directly. Typically, this ability is possessed only by certain bacteria (which have specific enzymes) like Cellulomonas etc, and which are often the flora on the gut walls of ruminants like cows and sheep, or by fungi, which in nature are responsible for cycling of nutrients. The enzymes utilized to cleave the glycosidic linkage in cellulose are glycoside hydrolases including endo-acting cellulases and exo-acting glucosidases. Such enzymes are usually secreted as part of multienzyme complexes that may include dockerins and cellulose binding modules, referred to in some cases as cellulosomes. Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... This article does not adequately cite its references or sources. ... A glycosidic bond is formed between a hemiacetal group of a sugar molecule (such as glucose) and an alcohol functional group to form an acetal. ... Glycoside hydrolases (also called glycosidases) catalyze the hydrolysis of the glycosidic linkage to generate two smaller sugars. ... Binding can mean: Binding (computer science) - a tie (for example) to certain names in programming languages Binding (knot) - A type of knot Binding (linguistics) - a property relating to anaphors (pronouns and R-expressions) and c-command Bookbinding - the protective cover of a book; and the art of constructing this Ski... Cellulosomes are complexes of enzymes created by bacteria such as Clostridium and Bacteroides, but functioning outside the cell. ...

Many cellulolytic bacteria, fungi or enzymes break down cellulose into shorter linked chains known as cellodextrins. Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... Cellodextrins are glucose polymers of varying length (2+ glucose monomers) resulting from the breakdown of cellulose. ...

Embodied Energy

Stub

Please insert calculations of chemical energy required to synthesis one molecular unit of cellulose, and energy released by burning one molecular unit of cellulose. This is significant for discussions on cellulose as replacement for fossil fuels.

Derivatives

The hydroxyl groups of cellulose can be partially or fully reacted with various chemicals to provide derivates with useful properties. Cellulose esters and cellulose ethers are the most important commercial materials. In principle, though not always in current industrial practice, cellulosic polymers are renewable resources. // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... General formula of a carboxylate ester. ... Ether is the general name for a class of chemical compounds which contain an ether group — an oxygen atom connected to two (substituted) alkyl groups. ...

Among the esters are cellulose acetate and cellulose triacetate, which are film- and fiber-forming materials that find a variety of uses. The inorganic ester nitrocellulose was initially used as an explosive and was an early film forming material. Cellulose acetate, first prepared in 1865, is the acetate ester of cellulose. ... Cellulose triacetate, also known simply as triacetate, is manufactured from cellulose and acetate. ... Skeletal formula of nitrocellulose Ball-and-stick model of a section of nitrocellulose Nitrocellulose (also: cellulose nitrate, flash paper) is a highly flammable compound formed by nitrating cellulose through, for example, exposure to nitric acid or another powerful nitrating agent. ...

Ether derivatives include

• Ethylcellulose, a water-insoluble commercial thermoplastic used in coatings, inks, binders, and controlled-release drug tablets;
• Hydroxypropyl cellulose;
• Carboxymethyl cellulose;
• Hydroxypropyl methyl cellulose, E464, used as a viscosity modifier, gelling agent, foaming agent and binding agent;
• Hydroxyethyl methyl cellulose, used in production of cellulose films.

Hydroxypropyl cellulose (cellulose, 2-hydroxypropyl ether) is a derivative of cellulose with both water solubility and organic solubility. ... Carboxymethyl cellulose, or CMC, is a cellulose derivative with carboxymethyl groups (-CH2-COOH) bound to some of the hydroxyl groups of the glucopyranose monomers that make up the cellulose backbone. ... For the mathematical constant see: E (mathematical constant). ...

References

Chemical Communications or ChemComm is a is a peer-reviewed scientific journal in the chemical sciences published since 1996 by the Royal Society of Chemistry. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

See also

• Cellulase
• Cell wall
• Ethanol fuel
• Hemicellulose
• Jungle rot
• Lignin
• Microcrystalline cellulose
• Proteonomics

Cellulase is an enzyme complex which breaks down cellulose to beta-glucose. ... A cell wall is a fairly rigid layer surrounding a cell, located external to the cell membrane, that provides the cell with structural support, protection, and a filtering mechanism. ... also used for chesse Information on pump, California. ... A hemicellulose can be any of several heteropolymers (matrix polysaccharides) present in almost all cell walls along with cellulose. ... Jungle rot is military jargon for fungal foot infection that is typically contracted in tropical climates. ... Lignin (sometimes lignen) is a chemical compound that is most commonly derived from wood and is an integral part of the cell walls of plants, especially in tracheids, xylem fibres and sclereids. ... Microcrystalline Cellulose is an excipient used in the formulation of tablets and capsules. ... This article or section is in need of attention from an expert on the subject. ...

External links

• LSBU cellulose page
• Clear description of a cellulose assay method at the Cotton Fiber Biosciences unit of the USDA.
• Cellulose films could provide flapping wings and cheap artificial muscles for robots - TechnologyReview.com
• Using cellulase enzymes in the bioethanol process.
• A list of cellulolytic bacteria.
• Links to external chemical sources