alpha-Glucose-1-phosphate

Title: a-Glucose-1-phosphate
CAS Registry Number: 59-56-3
CAS Name: a-D-Glucopyranose 1-dihydrogenphosphate
Additional Names: a-glucose-1-phosphoric acid; a-D-glucopyranose-1-phosphate; Cori ester
Molecular Formula: C6H13O9P
Molecular Weight: 260.14
Percent Composition: C 27.70%, H 5.04%, O 55.35%, P 11.91%
Literature 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 a-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).
Derivative Type: Free acid
Properties: [a]D25 +120°. pK1 = 1.11; pK2 = 6.13. Stronger acid than H3PO4. Extremely sol in water.
pKa: pK1 = 1.11; pK2 = 6.13
Optical Rotation: [a]D25 +120°
Derivative Type: Barium salt trihydrate
CAS Registry Number: 6056-70-8
Properties: Nonhygroscopic, stable powder. [a]D25 +75° (c = 1.26). Easily sol in water.
Optical Rotation: [a]D25 +75° (c = 1.26)
Derivative Type: Calcium salt
CAS Registry Number: 119119-85-6
Trademarks: Actigam (Daltan)
Derivative Type: Dipotassium salt dihydrate
CAS Registry Number: 5996-14-5
Properties: Crystals from ethanol. [a]D20 +78° (c = 4); [a]20549 +90° (c = 4). Freely sol in water.
Optical Rotation: [a]D20 +78° (c = 4); [a]20549 +90° (c = 4)
Therap-Cat: Calcium salt as roborant.
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