 | |
| 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 |
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| DrugBank |
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| ECHA InfoCard | 100.020.722 |
| KEGG |
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| UNII | |
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| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Rhamnose (Rha, Rham) is a naturally occurringdeoxy sugar. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Rhamnose predominantly occurs in nature in itsL-form asL-rhamnose (6-deoxy-L-mannose). This is unusual, since most of the naturally occurring sugars are inD-form. Exceptions are the methyl pentosesL-fucose andL-rhamnose and the pentoseL-arabinose. However, examples of naturally occurringD-rhamnose are found in some species of bacteria, such asPseudomonas aeruginosa andHelicobacter pylori.[2]
Rhamnose can be isolated frombuckthorn (Rhamnus),poison sumac, and plants in the genusUncaria. Rhamnose is also produced bymicroalgae belonging to classBacillariophyceae (diatoms).[3]
Rhamnose is commonly bound to other sugars in nature. It is a commonglycone component ofglycosides from many plants. Rhamnose is also a component of the outer cell membrane ofacid-fast bacteria in theMycobacterium genus, which includes the organism that causestuberculosis.[4] Natural antibodies againstL-rhamnose are present in human serum,[5] and the majority of people seem to possessIgM,IgG or both of these types ofimmunoglobulins capable of binding thisglycan.[6]
An interesting particularity of rhamnose is the presence offormaldehyde production when reacted withperiodates in thevicinaldiol cleavage reaction, that makes it very useful to remove excess periodate inglycerol or other vicinaldiol analysis, that would otherwise give colored blank issues.[7]
Disaccharides:
Polysaccharides:
Glycosides:
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| Monosaccharides |
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| Multiple |
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