Rhamnose

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Rhamnose [1]
Alpha-L-Rhamnopyranose.svg
Names
IUPAC name
6-Deoxy-L-mannopyranose
Systematic IUPAC name
(2R,3R,4R,5R,6S)-6-Methyloxane-2,3,4,5-tetrol
Other names
Isodulcit
α-L-Rhamnose
L-Rhamnose
L-Mannomethylose
α-L-Rha
α-L-Rhamnoside
α-L-Mannomethylose
6-Deoxy-L-mannose
L-Rhamnopyranose
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.020.722 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1 Yes check.svgY
    Key: PNNNRSAQSRJVSB-BXKVDMCESA-N Yes check.svgY
  • InChI=1/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1
    Key: PNNNRSAQSRJVSB-BXKVDMCEBH
  • O=C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C
Properties
C6H12O5
Molar mass 164.157 g·mol−1
Density 1.41 g/mL
Melting point 91 to 93 °C (196 to 199 °F; 364 to 366 K) (monohydrate)
-99.20·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rhamnose (Rha, Rham) is a naturally occurring deoxy sugar. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Rhamnose predominantly occurs in nature in its L-form as L-rhamnose (6-deoxy-L-mannose). This is unusual, since most of the naturally occurring sugars are in D-form. Exceptions are the methyl pentoses L-fucose and L-rhamnose and the pentose L-arabinose. However, examples of naturally-occurring D-rhamnose include some species of bacteria, such as Pseudomonas aeruginosa and Helicobacter pylori . [2]

Contents

Rhamnose can be isolated from buckthorn (Rhamnus), poison sumac, and plants in the genus Uncaria . Rhamnose is also produced by microalgae belonging to class Bacillariophyceae (diatoms). [3]

Rhamnose is commonly bound to other sugars in nature. It is a common glycone component of glycosides from many plants. Rhamnose is also a component of the outer cell membrane of acid-fast bacteria in the Mycobacterium genus, which includes the organism that causes tuberculosis. [4] Natural antibodies against L-rhamnose are present in human serum, [5] and the majority of people seem to possess IgM, IgG or both of these types of immunoglobulins capable of binding this glycan. [6]

An interesting particularity of rhamnose is the absence of formaldehyde production when reacted with periodates in the vicinal diol cleavage reaction, that makes it very useful to remove excess periodate in glycerol or other vicinal diol analysis, that would otherwise give colored blank issues. [7]

See also

Disaccharides:

Polysaccharides:

Glycosides:

Related Research Articles

<span class="mw-page-title-main">Carbohydrate</span> Organic compound that consists only of carbon, hydrogen, and oxygen

A carbohydrate is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1 and thus with the empirical formula Cm(H2O)n, which does not mean the H has covalent bonds with O. However, not all carbohydrates conform to this precise stoichiometric definition, nor are all chemicals that do conform to this definition automatically classified as carbohydrates.

<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.

<span class="mw-page-title-main">Polysaccharide</span> Long carbohydrate polymers comprising 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">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">Hexose</span> 6-Carbon simple sugar

In chemistry, a hexose is a monosaccharide (simple sugar) with six carbon atoms. The chemical formula for all hexoses is C6H12O6, and their molecular weight is 180.156 g/mol.

Carbohydrate metabolism is the whole of the biochemical processes responsible for the metabolic formation, breakdown, and interconversion of carbohydrates in living organisms.

A glucoside is a glycoside that is chemically derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes.

<span class="mw-page-title-main">Glycoside</span> Molecule in which a sugar is bound to another functional group

In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

<span class="mw-page-title-main">Glycolipid</span> Class of chemical compounds

Glycolipids are lipids with a carbohydrate attached by a glycosidic (covalent) bond. Their role is to maintain the stability of the cell membrane and to facilitate cellular recognition, which is crucial to the immune response and in the connections that allow cells to connect to one another to form tissues. Glycolipids are found on the surface of all eukaryotic cell membranes, where they extend from the phospholipid bilayer into the extracellular environment.

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

Fucose is a hexose deoxy sugar with the chemical formula C6H12O5. It is found on N-linked glycans on the mammalian, insect and plant cell surface. Fucose is the fundamental sub-unit of the seaweed polysaccharide fucoidan. The α(1→3) linked core of fucoidan is a suspected carbohydrate antigen for IgE-mediated allergy.

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.

<span class="mw-page-title-main">Isotype (immunology)</span>

In immunology, antibodies are classified into several types called isotypes or classes. The variable (V) regions near the tip of the antibody can differ from molecule to molecule in countless ways, allowing it to specifically target an antigen . In contrast, the constant (C) regions only occur in a few variants, which define the antibody's class. Antibodies of different classes activate distinct effector mechanisms in response to an antigen . They appear at different stages of an immune response, differ in structural features, and in their location around the body.

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">Rhamnolipid</span> Chemical compound

Rhamnolipids are a class of glycolipid produced by Pseudomonas aeruginosa, amongst other organisms, frequently cited as bacterial surfactants. They have a glycosyl head group, in this case a rhamnose moiety, and a 3-(hydroxyalkanoyloxy)alkanoic acid (HAA) fatty acid tail, such as 3-hydroxydecanoic acid.

UDP-2-acetamido-2-deoxy-ribo-hexuluronate aminotransferase is an enzyme with systematic name UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucuronate:2-oxoglutarate aminotransferase. This enzyme catalyses the following chemical reaction

Candida keroseneae is a species of yeast in the genus Candida, family Saccharomycetaceae. Described as new to science in 2011, it was isolated from aviation fuel.

Root mucilage is made of plant-specific polysaccharides or long chains of sugar molecules. This polysaccharide secretion of root exudate forms a gelatinous substance that sticks to the caps of roots. Root mucilage is known to play a role in forming relationships with soil-dwelling life forms. Just how this root mucilage is secreted is debated, but there is growing evidence that mucilage derives from ruptured cells. As roots penetrate through the soil, many of the cells surrounding the caps of roots are continually shed and replaced. These ruptured or lysed cells release their component parts, which include the polysaccharides that form root mucilage. These polysaccharides come from the Golgi apparatus and plant cell wall, which are rich in plant-specific polysaccharides. Unlike animal cells, plant cells have a cell wall that acts as a barrier surrounding the cell providing strength, which supports plants just like a skeleton.

The Criegee oxidation is a glycol cleavage reaction in which vicinal diols are oxidized to form ketones and aldehydes using lead tetraacetate. It is analogous to the use of periodate but uses a milder oxidant. This oxidation was discovered by Rudolf Criegee and coworkers and first reported in 1931 using ethylene glycol as the substrate.

Sulfoglycolysis is a catabolic process in primary metabolism in which sulfoquinovose (6-deoxy-6-sulfonato-glucose) is metabolized to produce energy and carbon-building blocks. Sulfoglycolysis pathways occur in a wide variety of organisms, and enable key steps in the degradation of sulfoquinovosyl diacylglycerol (SQDG), a sulfolipid found in plants and cyanobacteria into sulfite and sulfate. Sulfoglycolysis converts sulfoquinovose (C6H12O8S) into various smaller metabolizable carbon fragments such as pyruvate and dihydroxyacetone phosphate that enter central metabolism. The free energy is used to form the high-energy molecules ATP (adenosine triphosphate) and NADH (reduced nicotinamide adenine dinucleotide). Unlike glycolysis, which allows metabolism of all carbons in glucose, sulfoglycolysis pathways convert only a fraction of the carbon content of sulfoquinovose into smaller metabolizable fragments; the remainder is excreted as C3-sulfonates 2,3-dihydroxypropanesulfonate (DHPS) or sulfolactate (SL); or C2-sulfonates isethionate or sulfoacetate.

The enterobacterial common antigen (ECA) is a carbohydrate antigen found in the outer membrane of many Enterobacterales species. The antigen is unanimously absent from other gram-negative and gram-positive bacteria. Aeromonas hydrophila 209A is the only organism outside of Enterobacterales that expresses the ECA. More studies are needed to explain the presence of the antigen in this species as no other strains of this species express the antigen. The ECA is a polysaccharide made of repeating units of trisaccharides. The functions of these units have very few proven functions. Some evidence indicates role in pathogenicity in the bacteria that present the ECA. There are three separate types of ECA these include ECAPG, ECALPS, and ECACYC, each have different lengths. The synthesis of the ECA is controlled by the wec operon and has a 12-step synthesis which is described below. Due to the lack of proven function of the ECA, any clinical significance is hard to define however, some evidence suggests that human serum has antibodies against ECA.

References

  1. Merck Index, 11th Edition, 8171.
  2. Melamed J, Kocev A, Torgov V, Veselovsky V, Brockhausen I (2022). "Biosynthesis of the Pseudomonas aeruginosa common polysaccharide antigen by D‐Rhamnosyltransferases WbpX and WbpY". Glycoconjugate Journal. doi:10.1007/s10719-022-10040-4. PMC   8853325 . PMID   35166992.
  3. Brown, M. R. (1991). "The amino-acid and sugar composition of 16 species of microalgae used in mariculture". Journal of Experimental Marine Biology and Ecology. 145: 79. doi:10.1016/0022-0981(91)90007-J.
  4. Golan, David E., ed. (2005). "Chapter 35 - Pharmacology of the Bacterial Cell Wall". Principles of Pharmacology: The Pathophysiologic Basis of Drug Therapy. Armen H. Tashjian Jr., Ehrin J. Armstrong, Joshua N. Galanter, April Wang Armstrong, Ramy A. Arnaout, Harris S. Rose. Lippincott Williams and Wilkins. p. 569. ISBN   0-7817-4678-7.
  5. Oyelaran O, McShane LM, Dodd L, Gildersleeve JC (2009). "Profiling Human Serum Antibodies with a Carbohydrate Antigen Microarray". J. Proteome Res. 8 (9): 4301–10. doi:10.1021/pr900515y. PMC   2738755 . PMID   19624168.
  6. Wang X, Chen H, Chiodo F, Tefsen B (2019). "Detection of human IgM and IgG antibodies by means of galactofuranose-coated and rhamnose-coated gold nanoparticles". Matters. https://sciencematters.io/articles/201908000004
  7. Ashworth, M. R. F., ed. (1979). "Chapter 3". Analytical methods for glycerol. Academic Press.

Further reading