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Rhamnose information


Rhamnose[1]
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
CAS Number
  • 3615-41-6 ☒N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16055 checkY
ChemSpider
  • 18150 checkY
DrugBank
  • DB01869 checkY
ECHA InfoCard 100.020.722 Edit this at Wikidata
KEGG
  • C00507 checkY
PubChem CID
  • 19233
UNII
  • QN34XC755A checkY
CompTox Dashboard (EPA)
  • DTXSID7042647 Edit this at Wikidata
InChI
  • 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 checkY
    Key: PNNNRSAQSRJVSB-BXKVDMCESA-N checkY
  • 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
SMILES
  • O=C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C
Properties
Chemical formula
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)
Magnetic susceptibility (χ)
-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).
☒N verify (what is checkY☒N ?)
Infobox references

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]

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 presence 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]

  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.

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Hexose

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Glycoside

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Glucoside

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the most common sugar present in glucosides, many are known which yield rhamnose or iso-dulcite; these may be termed pentosides. Much attention has been...

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Spinosad

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attached to an amino sugar (D-forosamine) and a neutral sugar (tri-Ο-methyl-L-rhamnose). Spinosad is relatively nonpolar and not easily dissolved in water. Spinosad...

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Disaccharide

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galactose and one fructose β(1→4) Rutinose One rhamnose and one glucose α(1→6) Rutinulose One rhamnose and one fructose β(1→6) Xylobiose Two xylopyranoses...

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Xanthan gum

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Carbohydrate

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Sugar

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Quercus robur

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dilactone, monogalloyl glucose, digalloyl glucose, trigalloyl glucose, rhamnose, quercitrin and ellagic acid are phenolic compounds found in Q. robur....

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Fructooligosaccharide

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Strawberry

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substituting sugar in strawberry anthocyanins, rutinose, arabinose, and rhamnose conjugates have been found in some strawberry cultivars. Purple minor pigments...

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Polysaccharide

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Isomaltooligosaccharide

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