D-Allose

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General description of D-Allose:

D-Allose (CPA) or β-D-Allopyranose [2595-97-3] is an aldohexose monosacharid, C-3 epimer of glucose. Pure comound is colorless (white) crystalline solid with the melting point of 141-142 °C^[1] and a rotation at equilibrium [α] +14.5° in water.^[2] It is classified as rare sugar. D-Allose is a low-calorie sweetener (20% less sweetness than sucrose), non-toxic and it can be easily dissolved in water but it is practically insoluble in methanol. It can be found in various plant species, such as Protea rubropilosa, Veronica filiformis, Mantzelia spp. Solanum tuberosum and others.^[3] Convenient laboratory preparation is based on conversion of stereochemistry of C3-hydroxy group of 1,2,5,6-di-O-isopropylidene-α-D-glucofuranose by chemical oxidation to ketone and subsequent stereospecific reduction with borohydride followed by acetals hydrolysis with Amberlite H⁺ resine.^[2] Large scale bioproduction strategy consists of enzymatic isomerisation of D-psicose (formed biochemically from D-fructose) to D-allose, catalysed by enzyme L-rhamonose isomerase.^[4] Authors proposed the bioproduction strategy route to all rare sugars in a ring form as „Izumoring“.^[5]

Application:

Cancer and tumor inhibition is considered to be the most important property of D-allose. It has been reported to be effective against various human cancers.^[6] Furthermore, radiation, when coupled with D-allose, stimulates the production of reactive oxygen species in cancer cells to a significantly higher extent and has an approximately five times larger effect on apoptosis.^[7] It also acts as an immunosuppressant^[8] and due to its anti-inflammatory effect, D-allose can also mitigate cisplatin-induced nephrotoxicity.^[9]

Product categorization (Chemical groups):

Main category:

• Alcohols / Phenols / Hydroxy compounds
• Sugar derivatives

Second level:

• Aliphatic

Third level:

• Heterocyclic compounds

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