Structure via PubChem · Public domain (PubChem)
rhamnose (aldehydo)
Also known as L-Rha, (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal, rhamnose
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 are found in some species of bacteria, such as Pseudomonas aeruginosa and Helicobacter pylori.
Chemical data
- Formula
- C6H12O5
- Molecular weight
- 164.16 g/mol
- IUPAC name
- (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal
- SMILES
- C[C@@H]([C@@H]([C@H]([C@H](C=O)O)O)O)O
- InChIKey
- PNNNRSAQSRJVSB-BXKVDMCESA-N
- XLogP
- -2.4
- Polar surface area
- 98 Ų
- H-bond donors
- 4
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
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Article
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- Further reading
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 are found in some species of bacteria, such as Pseudomonas aeruginosa and Helicobacter pylori.
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).