Rhamnose












































































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

CAS Number

  • 3615-41-6 ☒N

3D model (JSmol)
  • Interactive image

ChEBI

  • CHEBI:16055 ☑Y

ChemSpider

  • 18150 ☑Y

DrugBank

  • DB01869 ☑Y

KEGG

  • C00507 ☑Y


PubChem CID
  • 19233

UNII

  • QN34XC755A ☑Y




Properties

Chemical formula
C6H12O5

Molar mass
 164.16 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 ☑Y☒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 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.


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).[2]


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.[3]



See also




  • Galactose binding lectin domain, despite the name, often binds rhamnose

  • Alpha-L-rhamnosidase


Disaccharides:




  • Rutinose, rhamnose-glucose


  • Neohesperidose, rhamnose-glucose


  • Robinose, rhamnose-galactose


Glycosides:



  • Category:Rhamnosides

  • Echinacoside

  • Rhamnolipid

  • Verbascoside



References




  1. ^ Merck Index, 11th Edition, 8171.


  2. ^ 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..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}


  3. ^ 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.



Further reading



  • Watanabe, K; Takesue, S (1975). "Use of L-rhamnose to Study Irreversible Adsorption of Bacteriophage PL-1 to a Strain of Lactobacillus casei". Journal of General Virology. 28 (1): 29–35. doi:10.1099/0022-1317-28-1-29. PMID 239994.








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