Mannans

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Subunit of a typical mannan showing four 1,4-linked beta-D-mannose units, one with a galactose side chain. Mannan with galactose side chain.svg
Subunit of a typical mannan showing four 1,4-linked beta-D-mannose units, one with a galactose side chain.

Mannans are polymers containing the sugar mannose as a principal component. [1] [2] They are a type of polysaccharide found in hemicellulose, a major source of biomass found in higher plants such as softwoods. These polymers also typically contain two other sugars, galactose and glucose. They are often branched (unlike cellulose).

Contents

Structural diversity

Plant mannans have β(1-4) linkages, occasionally with α(1-6) galactose branches, forming galactomannans. They are insoluble and a form of storage polysaccharide. Ivory nut is a source of mannans. An additional type is galactoglucomannan found in soft wood with a mixed mannose/glucose β(1-4) backbone. Many mannans are acetylated and some from marine sources, have sulfate esters side chains.

Yeast and some plants such as conjac and salep have a different type of mannans in their cell wall, with a α(1-6) linked backbone and α(1-2) and α(1-3) linked glucose branches, hence "glucomannan". It is water soluble. It is serologically similar to structures found on mammalian glycoproteins. Detection of mannan leads to lysis in the mannan-binding lectin pathway.[ citation needed ]

Synthesis and degradation

Guanosine diphosphate mannose is the precursor to mannans. GDP-mannose.svg
Guanosine diphosphate mannose is the precursor to mannans.

GDP-mannose is a substrate for glycosyltransferase for enzymes called mannosyltransferases. [4]

Biosynthesis

GDP-mannose is produced from GTP and mannose-6-phosphate by the enzyme mannose-1-phosphate guanylyltransferase.

The degradation of mannans (and many related forms of hemicellulose) has been well studied. The hydrolysis of the main mannan backbone is catalyzed by various enzymes including β-mannosidase, β-glucosidase, and β-mannase. The side chains are degraded by esterases and α-galactosidase. [1]

When a long chain of mannan is hydrolyzed into shorter chains, these smaller molecules are known as mannan oligosaccharide (MOS). MOS by definition can be produced from either insoluble galactomannan or soluble glucomannan, although the latter type is more widely marketed. [5]

Glucomannan MOS is used as prebiotics in animal husbandry and nutritional supplements due to its bioactivity.[ citation needed ]

Etymology

From 'manna', produced by several species of tree and shrub e.g. Fraxinus ornus from whose secretions mannitol was originally isolated.

See also

Related Research Articles

<span class="mw-page-title-main">Glucose</span> Naturally produced monosaccharide

Glucose is a sugar with the molecular formula C6H12O6. Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world.

<span class="mw-page-title-main">Hemicellulose</span> Class of plant cell wall polysaccharides

A hemicellulose is one of a number of heteropolymers, such as arabinoxylans, present along with cellulose in almost all terrestrial plant cell walls. Cellulose is crystalline, strong, and resistant to hydrolysis. Hemicelluloses are branched, shorter in length than cellulose, and also show a propensity to crystallize. They can be hydrolyzed by dilute acid or base as well as a myriad of hemicellulase enzymes.

Hydrolysis is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.

<span class="mw-page-title-main">Polysaccharide</span> Long carbohydrate polymers such as starch, glycogen, cellulose, and chitin

Polysaccharides, or polycarbohydrates, are the most abundant carbohydrates found in food. They are long-chain polymeric carbohydrates composed of monosaccharide units bound together by glycosidic linkages. This carbohydrate can react with water (hydrolysis) using amylase enzymes as catalyst, which produces constituent sugars. They range in structure from linear to highly branched. Examples include storage polysaccharides such as starch, glycogen and galactogen and structural polysaccharides such as cellulose and chitin.

<span class="mw-page-title-main">Starch</span> Glucose polymer used as energy store in plants

Starch or amylum is a polymeric carbohydrate consisting of numerous glucose units joined by glycosidic bonds. This polysaccharide is produced by most green plants for energy storage. Worldwide, it is the most common carbohydrate in human diets, and is contained in large amounts in staple foods such as wheat, potatoes, maize (corn), rice, and cassava (manioc).

<span class="mw-page-title-main">Galactose</span> Monosaccharide sugar

Galactose, sometimes abbreviated Gal, is a monosaccharide sugar that is about as sweet as glucose, and about 65% as sweet as sucrose. It is an aldohexose and a C-4 epimer of glucose. A galactose molecule linked with a glucose molecule forms a lactose molecule.

<span class="mw-page-title-main">Mannose</span> Chemical compound

Mannose is a sugar monomer of the aldohexose series of carbohydrates. It is a C-2 epimer of glucose. Mannose is important in human metabolism, especially in the glycosylation of certain proteins. Several congenital disorders of glycosylation are associated with mutations in enzymes involved in mannose metabolism.

<span class="mw-page-title-main">Cellulase</span> Class of enzymes

Cellulase is any of several enzymes produced chiefly by fungi, bacteria, and protozoans that catalyze cellulolysis, the decomposition of cellulose and of some related polysaccharides:

An oligosaccharide is a saccharide polymer containing a small number of monosaccharides. Oligosaccharides can have many functions including cell recognition and cell adhesion.

<span class="mw-page-title-main">Glycosaminoglycan</span> Polysaccharides found in animal tissue

Glycosaminoglycans (GAGs) or mucopolysaccharides are long, linear polysaccharides consisting of repeating disaccharide units. The repeating two-sugar unit consists of a uronic sugar and an amino sugar, except in the case of the sulfated glycosaminoglycan keratan, where, in place of the uronic sugar there is a galactose unit. GAGs are found in vertebrates, invertebrates and bacteria. Because GAGs are highly polar molecules and attract water; the body uses them as lubricants or shock absorbers.

<span class="mw-page-title-main">Glucomannan</span> Chemical compound

Glucomannan is a water-soluble polysaccharide that is considered a dietary fiber. It is a hemicellulose component in the cell walls of some plant species. Glucomannan is a food additive used as an emulsifier and thickener. It is a major source of mannan oligosaccharide (MOS) found in nature, the other being galactomannan, which is insoluble.

The terms glycans and polysaccharides are defined by IUPAC as synonyms meaning "compounds consisting of a large number of monosaccharides linked glycosidically". However, in practice the term glycan may also be used to refer to the carbohydrate portion of a glycoconjugate, such as a glycoprotein, glycolipid, or a proteoglycan, even if the carbohydrate is only an oligosaccharide. Glycans usually consist solely of O-glycosidic linkages of monosaccharides. For example, cellulose is a glycan composed of β-1,4-linked D-glucose, and chitin is a glycan composed of β-1,4-linked N-acetyl-D-glucosamine. Glycans can be homo- or heteropolymers of monosaccharide residues, and can be linear or branched.

α-Galactosidase Enzyme

α-Galactosidase is a glycoside hydrolase enzyme that catalyses the following reaction:

<span class="mw-page-title-main">Glycosyltransferase</span> Class of enzymes

Glycosyltransferases are enzymes that establish natural glycosidic linkages. They catalyze the transfer of saccharide moieties from an activated nucleotide sugar to a nucleophilic glycosyl acceptor molecule, the nucleophile of which can be oxygen- carbon-, nitrogen-, or sulfur-based.

<span class="mw-page-title-main">Xylan</span> A plant cell wall polysaccharide

Xylan is a type of hemicellulose, a polysaccharide consisting mainly of xylose residues. It is found in plants, in the secondary cell walls of dicots and all cell walls of grasses. Xylan is the third most abundant biopolymer on Earth, after cellulose and chitin.

Oligosaccharides and polysaccharides are an important class of polymeric carbohydrates found in virtually all living entities. Their structural features make their nomenclature challenging and their roles in living systems make their nomenclature important.

<i>N</i>-linked glycosylation Attachment of an oligosaccharide to a nitrogen atom

N-linked glycosylation, is the attachment of an oligosaccharide, a carbohydrate consisting of several sugar molecules, sometimes also referred to as glycan, to a nitrogen atom, in a process called N-glycosylation, studied in biochemistry. The resulting protein is called an N-linked glycan, or simply an N-glycan.

Galactoglucomannan is a water-soluble hemicellulose, consisting of galactose, glucose and mannose. Many softwood species, e.g. Norway spruce are rich of galactoglucomannans and can contain it up to 10–20%.

Core oligosaccharide is a short chain of sugar residues within Gram-negative lipopolysaccharide (LPS). Core-OS are highly diverse among bacterial species and even within strains of species

<span class="mw-page-title-main">Galactogen</span> Chemical compound

Galactogen is a polysaccharide of galactose that functions as energy storage in pulmonate snails and some Caenogastropoda. This polysaccharide is exclusive of the reproduction and is only found in the albumen gland from the female snail reproductive system and in the perivitelline fluid of eggs.

References

  1. 1 2 Moreira, L. R. S.; Filho, E. X. F. (2008). "An overview of mannan structure and mannan-degrading enzyme systems". Applied Microbiology and Biotechnology. 79 (2): 165–178. doi:10.1007/s00253-008-1423-4. PMID   18385995. S2CID   9746196.
  2. Mannan at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
  3. Samuel G, Reeves P (2003). "Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly". Carbohydrate Research. 338 (23): 2503–19. doi:10.1016/j.carres.2003.07.009. PMID   14670712.
  4. Pauly, Markus; Gille, Sascha; Liu, Lifeng; Mansoori, Nasim; De Souza, Amancio; Schultink, Alex; Xiong, Guangyan (2013). "Hemicellulose biosynthesis". Planta. 238 (4): 627–642. doi:10.1007/s00425-013-1921-1. PMID   23801299. S2CID   17501948.
  5. Nopvichai, C; Charoenwongpaiboon, T; Luengluepunya, N; Ito, K; Muanprasat, C; Pichyangkura, R (2019). "Production and purification of mannan oligosaccharide with epithelial tight junction enhancing activity". PeerJ. 7: e7206. doi: 10.7717/peerj.7206 . PMC   6611449 . PMID   31304065. MOS is often prepared by hydrolysis reaction of a mannose-contained glucan polymer, mainly glucomannan and galactomannan.

Further reading