D-allose-6-phosphate

This enzyme [EC 2.7.1.55], also referred to as allokinase, catalyzes the reaction of ATP with D-aUose to yield ADP and D-allose 6-phosphate. 

The presence of substituents outside the ring usually does not affect the composition. Thus, D-allose 6-phosphate, D-altrose 6-phosphate, and d-manno-heptulose 7-phosphate have practically the same composition as the parent sugars.51... 

D-Allose 6-phosphate Q-glycero -n-altro -octulose 8-phosphate 0.1 80 TK 250 58... 

Chemical Synthesis.—Purine nucleoside 5 -monophosphates enriched with or 0 on the phosphate group are conveniently prepared by treating phosphorus pentachloride in dry triethyl phosphate with one equivalent of the appropriately labelled water to give PO]- or P 0]P0Cl3, which is not isolated but mixed with adenosine or guanosine in the same solvent. Work-up of the resulting 5 -phos-phorodichloridate in similarly labelled water permits the formation of pO]-or P 0]AMP (or GMP) in fair yield with good enrichment. The 5 -monophos-phates of the 5 -C-methyl uridines derived from 6-deoxy-D-allose and 6-deoxy-L-talose have been prepared via phosphorylation of the 2, 3 -0,0-ethoxymethyl-idene derivative of the nucleosides (1) with -cyanoethyl phosphate and DCC or TPS-Cl. The same method has been used to phosphorylate iV -benzoylated 2, 3 -0,C -isopropylidene derivatives of various 5 -C-alkyladenosine species (2) and also 4 -allyladenosine (3) as part of a study in which derivatives of AMP... 

In the presence of formaldehyde (0.5 mol equiv.), sugar phosphates were formed in up to 45% yield, with pentose-2,4-diphosphates dominating over hexose triphosphates by a ratio of 3 1 (Scheme 13.2, Route B). The major component was found to be D,L-ribose-2,4-diphosphate with the ratios of ribose-, arabinose-, lyxose-, and xylose-2,4-diphosphates being 52 14 23 11, respectively. The aldomerization of 2 in the presence of H2CO is a variant of the formose reaction. It avoids the formation of complex product mixtures as a consequence of the fact that aldoses, which are phosphorylated at the C(2) position, cannot undergo aldose-ketose tautomerization. The preference for ribose-2,4-diphosphate 5 and allose-2,4,6-triphosphate formation might be relevant to a discussion of the origin of ribonucleic acids. 

Muller, D, Pitsch, S, Kittaka, A, Wagner, E, Wintner, C E, Eschenmoser, A, Chemie von a-Aminonitrilen. Aldomerisierung von Glycolaldehyd-phosphat zu racemischen Hexose-2,4,6-triphosphaten und (in Gegenwart von Eormaldehyd) racemischen Pentose-2,4-diphosphaten rac-Allose-2,4,6-triphosphat und rac-Ribose-2,4-diphosphat sind die Reaktionhauptprodukte, Helv. Chim. Acta, 73, 1410-1468, 1990. 

---