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Carbon-13-enriched Carbohydrates: Preparation of Triose, Tetrose, and Pentose Phosphates

Carbon-13-enriched Carbohydrates: Preparation of Triose, Tetrose, and Pentose Phosphates

A S Serianni, J Pierce, R Barker

Biochemistry. 1979 Apr 3;18(7):1192-9.

PMID: 218615

Abstract:

Three-, four-, and five-carbon aldononitrile phosphates were prepared, purified, and catalyticlly reduced with palladium--barium sulfate (5%) to the corresponding aldose phosphates in high yields at pH 1.7 +/- 0.1 and atmopsheric pressure. DL-Glyceraldehyde 3-phosphate and the tetrose 4-phosphates were prepared with carbon-13 enrichment at C-1, while the pentose 5-phosphates were prepared with enrichment at C-1 and C-2. Preparations of glycolaldehyde phosphate and d-glyceraldehyde 3-phosphate by lead tetra-acetate oxidation of glycerol phosphate and fructose 6-phosphate, respectively, are described. The proportions of cyclic hemiacetals and linear gem-diol forms of the two- to five-carbon aldose phosphates in aqueous solution are reported. Carbon-13 chemical shifts and carbon--phosphorus and carbon--hydrogen coupling constants for the furanose phosphate ring and linear gem-diol phosphates are reported and discussed. d-[2(-13)C]Ribulose 1,5-bisphosphate and L-[3,4(-13)C]sorbose 1,6-bisphosphate were prepared enzymatically from D-[2(-13)C]ribose 5-phosphate and dl-[1(-13)C]glyceraldehyde 3-phosphate, respectively.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP591593	DL-Glyceraldehyde 3-phosphate solution		591-59-3	Price
LS72305	Palladium on barium sulfate			Price

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