4461. α-Glucose-1-phosphate

Nomenclature

CAS number: 59-56-3
α-d-Glucopyranose 1-dihydrogenphosphate; α-glucose-1-phosphoric acid; α-d-glucopyranose-1-phosphate; Cori ester.
C6H13O9P; mol wt 260.14.
C 27.70%, H 5.04%, O 55.35%, P 11.91%.

Description and references

Found widely in both plants and animals. In plants it is the immediate precursor of starch, and in animals of glycogen, being also the first product in the breakdown and utilization of these substances. Isoln from muscle and synthesis using trisilver phosphate: Cori et al., J. Biol. Chem. 121, 465 (1937); Krahl, Cori, Biochem. Prep. 1, 33 (1949). Prepn from α-acetobromglucose + silver diphenyl phosphate: Posternak, J. Am. Chem. Soc. 72, 4824 (1950); by phosphorolysis of starch using phosphorylase and orthophosphate: McCready, Hassid, Biochem. Prep. 4, 63 (1955). Structure: Wolfrom, Pletcher, J. Am. Chem. Soc. 63, 1050 (1941). Configuration: Wolfrom et al., ibid. 64, 23 (1942); Harmon, Diss. Abstr. 24, 4400 (1964); Beevers, Maconochie, Acta Crystallogr. 18, 232 (1965).

Chemical structure

Derivative

Free acid.

Properties

[α]D25 +120°. pK1 = 1.11; pK2 = 6.13. Stronger acid than H3PO4. Extremely sol in water.

Derivative

Barium salt trihydrate.

Nomenclature

CAS number: 6056-70-8

Properties

Nonhygroscopic, stable powder. [α]D25 +75° (c = 1.26). Easily sol in water.

Derivative

Calcium salt.

Nomenclature

CAS number: 119119-85-6
Actigam (Daltan).

Derivative

Dipotassium salt dihydrate.

Nomenclature

CAS number: 5996-14-5

Properties

Crystals from ethanol. [α]D20 +78° (c = 4); [α]20549 +90° (c = 4). Freely sol in water.

Therapeutic Category

Calcium salt as roborant.