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Raffinose

Raffinose
IUPAC name	(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-[ [(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-3,4,5-triol
Other names	Melitose Melitriose Gossypose α-D-Galactosylsucrose
Identifiers
CAS number	512-69-6, [7629-30-0] (pentahydrate)
PubChem	439242
SMILES	C([C@@H]1[C@@H]([C@@H]([C@H] ([C@H](O1)OC[C@@H]2[C@H]([C@@H] ([C@H]([C@H](O2)O[C@]3([C@H]([C@@H] ([C@H](O3)CO)O)O)CO)O)O)O)O)O)O)O
Properties
Molecular formula	C₁₈H₃₂O₁₆
Molar mass	504.42 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Raffinose is a trisaccharide composed of galactose, fructose, and glucose. It can be found in beans, cabbage, brussels sprouts, broccoli, asparagus, other vegetables, and whole grains. Raffinose can be hydrolyzed to D-galactose and sucrose by the enzyme α-galactosidase (α-GAL), an enzyme not found in humans. α-GAL also hydrolyzes other α-galactosides such as stachyose, verbascose, and galactinol, if present. The enzyme does not cleave β-linked galactose, as in lactose.

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The raffinose family of oligosaccharides (RFOs) are alpha-galactosyl derivatives of sucrose, and the most common are the trisaccharide raffinose, the tetrasaccharide stachyose, and the pentasaccharide verbascose. RFOs are almost ubiquitous in the plant kingdom, being found in a large variety of seeds from many different families, and they rank second only to sucrose in abundance as soluble carbohydrates.

Humans and other monogastric animals (pigs and poultry) do not possess the α-GAL enzyme to break down RFOs and these oligosaccharides pass undigested through the stomach and upper intestine. In the lower intestine, they are fermented by gas-producing bacteria which do posses the α-GAL enzyme and make carbon dioxide, methane, and/or hydrogen -- leading to the flatulence commonly associated with eating beans and other vegetables. α-GAL is present in digestive aids such as the product Beano.

Procedures concerning cryopreservation have utilized raffinose to provide hypertonicity for cell desiccation prior to freezing ^[1]. Either raffinose or sucrose is used as a base substance for sucralose.

References

^ Storey B., Noiles, E., Thompson, K. (1998). "Comparison of Glycerol, Other Polyols, Trehalose, and Raffinose to Progive a defined cryoprotectant Medium for Mouse Sperm Cryopreservation". Cryobiology 37: 46-58.

Categories: Carbohydrates | Oligosaccharides