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Rhamnose

Rhamnose^[1]

IUPAC name	(2R,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol
Identifiers
CAS number	10485-94-6
SMILES	O[C@H]1C(C)O[C@@H] (O)[C@@H](O)[C@@H]1O
Properties
Molecular formula	C₆H₁₂O₅
Molar mass	164.16 g/mol
Melting point	91-93 °C (monohydrate)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Rhamnose is a naturally-occurring deoxy sugar. It can be classified either as 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.

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L-Rhamnose can be isolated from Buckthorn (Rhamnus) and poison sumac. It is also found as a glycoside in a variety of other plants.

Rhamnose is a component of the outer cell membrane of acid-fast bacteria in the Mycobacterium genus, which includes the organsism that causes tuberculosis.^[2]

References

^ Merck Index, 11th Edition, 8171.
^ (2005) "Chapter 35 - Pharmacology of the Bacterial Cell Wall", in Golan, David E.: 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 (in English), Lippincott Williams and Wilkins, 569. ISBN 0-7817-4678-7.

General:	Aldose \| Ketose \| Pyranose \| Furanose
Geometry:	Triose \| Tetrose \| Pentose \| Hexose \| Heptose \| Cyclohexane conformation \| Anomer \| Mutarotation
Small/Large:	Glyceraldehyde \| Dihydroxyacetone \| Erythrose \| Threose \| Erythrulose \| Sedoheptulose
Trioses:	ketotriose \| Aldotriose
Tetroses:	Erythrulose \| Erythrose \| Threose
Pentoses:	Arabinose \| Deoxyribose \| Lyxose \| Ribose \| Ribulose \| Xylose \| Xylulose
Hexoses:	Glucose \| Galactose \| Mannose \| Gulose \| Idose \| Talose \| Allose \| Altrose \| Fructose \| Sorbose \| Tagatose \| Psicose \| Fucose \| Rhamnose
Disaccharides:	Sucrose \| Lactose \| Trehalose \| Maltose
Polymers:	Glycogen \| Starch (Amylose \| Amylopectin) \| Cellulose \| Chitin \| Stachyose \| Inulin \| Dextrin
Glycosaminoglycans:	Heparin \| Chondroitin sulfate \| Hyaluronan \| Heparan sulfate \| Dermatan sulfate \| Keratan sulfate
Aminoglycosides:	Kanamycin \| Streptomycin \| Tobramycin \| Neomycin \| Paromomycin \| Apramycin \| Gentamicin \| Netilmicin \| Amikacin