Rhamnose (Rha, Rham) is a naturally occurring

deoxy sugar Deoxy sugars are sugars that have had a hydroxyl group replaced with a hydrogen atom. Examples include: * Deoxyribose, or 2-deoxy-D-ribose, a constituent of DNA * Fucose, or 6-deoxy-L-galactose, main component of fucoidan of brown algae, and pr ...

. It can be classified as either a methyl-

pentose In chemistry, a pentose is a monosaccharide (simple sugar) with five carbon atoms. The chemical formula of many pentoses is , and their molecular weight is 150.13 g/mol.hexose In chemistry, a hexose is a monosaccharide (simple sugar) with six carbon atoms. The chemical formula for all hexoses is , and their molecular weight is 180.156 g/mol. Hexoses exist in two forms, open-chain or cyclic, that easily convert into ...

. Rhamnose predominantly occurs in nature in its L-form as L-rhamnose (6-deoxy-L-

mannose Mannose is a sugar with the formula , which sometimes is abbreviated Man. It is one of the monomers of the aldohexose series of carbohydrates. It is a C-2 epimer of glucose. Mannose is important in human metabolism, especially in the glycosylatio ...

). This is unusual, since most of the naturally occurring sugars are in D-form. Exceptions are the methyl pentoses L-

fucose 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) l ...

and L-rhamnose and the pentose L-

arabinose Arabinose is an aldopentose – a monosaccharide containing five carbon atoms, and including an aldehyde (CHO) functional group. Properties For biosynthetic reasons, most saccharides are almost always more abundant in nature as the "D"-form, o ...

. However, examples of naturally-occurring D-rhamnose are found in some species of bacteria, such as ''

Pseudomonas aeruginosa ''Pseudomonas aeruginosa'' is a common Bacterial capsule, encapsulated, Gram-negative bacteria, Gram-negative, Aerobic organism, aerobic–facultative anaerobe, facultatively anaerobic, Bacillus (shape), rod-shaped bacteria, bacterium that can c ...

'' and ''

Helicobacter pylori ''Helicobacter pylori'', previously known as ''Campylobacter pylori'', is a gram-negative, Flagellum#bacterial, flagellated, Bacterial cellular morphologies#Helical, helical bacterium. Mutants can have a rod or curved rod shape that exhibits l ...

''. Rhamnose can be isolated from

buckthorn ''Rhamnus'' is a genus of about 140 accepted species of shrubs or small trees, commonly known as buckthorns, in the family Rhamnaceae. Its species range from tall (rarely to ) and are native mainly in east Asia and North America, but found thr ...

(''Rhamnus''),

poison sumac ''Toxicodendron vernix'', commonly known as poison sumac, or swamp-sumach, is a woody shrub or small tree growing to tall. It was previously known as ''Rhus vernix''. This plant is also known as thunderwood, particularly where it occurs in the ...

, and plants in the genus ''

Uncaria ''Uncaria'' is a genus of flowering plants in the Family (biology), family Rubiaceae. It has about 40 species.''Uncaria'' At: World Checklist of Rubiaceae At: Kew Gardens Website. (see ''External links'' below). Their Range (biology), distribut ...

''. Rhamnose is also produced by

microalgae Microalgae or microphytes are microscopic scale, microscopic algae invisible to the naked eye. They are phytoplankton typically found in freshwater and marine life, marine systems, living in both the water column and sediment. They are unicellul ...

belonging to class Bacillariophyceae (diatoms). Rhamnose is commonly bound to other sugars in nature. It is a common glycone component of

glycoside 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. ...

s from many plants. Rhamnose is also a component of the outer cell membrane of

acid-fast Acid-fastness is a physical property of certain bacterial and eukaryotic cells, as well as some sub-cellular structures, specifically their resistance to decolorization by acids during laboratory staining procedures. Once stained as part of a sa ...

bacteria in the ''

Mycobacterium ''Mycobacterium'' is a genus of over 190 species in the phylum Actinomycetota, assigned its own family, Mycobacteriaceae. This genus includes pathogens known to cause serious diseases in mammals, including tuberculosis (''Mycobacterium tuberculo ...

'' genus, which includes the organism that causes

tuberculosis Tuberculosis (TB), also known colloquially as the "white death", or historically as consumption, is a contagious disease usually caused by ''Mycobacterium tuberculosis'' (MTB) bacteria. Tuberculosis generally affects the lungs, but it can al ...

. Natural antibodies against L-rhamnose are present in human serum, and the majority of people seem to possess

IgM Immunoglobulin M (IgM) is the largest of several isotypes of antibodies (also known as immunoglobulin) that are produced by vertebrates. IgM is the first antibody to appear in the response to initial exposure to an antigen; causing it to also ...

IgG Immunoglobulin G (IgG) is a type of antibody. Representing approximately 75% of serum antibodies in humans, IgG is the most common type of antibody found in blood circulation. IgG molecules are created and released by plasma B cells. Each IgG ant ...

or both of these types of

immunoglobulins An antibody (Ab) or immunoglobulin (Ig) is a large, Y-shaped protein belonging to the immunoglobulin superfamily which is used by the immune system to identify and neutralize antigens such as bacteria and viruses, including those that cause di ...

capable of binding this

glycan 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 ...

. An interesting particularity of rhamnose is the presence of

formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...

production when reacted with

periodate Periodate ( ) is an anion composed of iodine and oxygen. It is one of a number of oxyanions of iodine and is the highest in the series, with iodine existing in oxidation state +7. Unlike other perhalogenates, such as perchlorate, it can exist in ...

s in the vicinal

diol cleavage Glycol cleavage is a specific type of organic chemistry oxidation. The carbon–carbon bond in a vicinal diol (glycol) is cleaved and instead the two oxygen atoms become double-bonded to their respective carbon atoms. Depending on the substituti ...

reaction, that makes it very useful to remove excess periodate in

glycerol Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...

or other vicinal

diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting gro ...

analysis, that would otherwise give colored blank issues.

See also

References

Further reading