Synthesis of Analogues of 1,3-Dihydroxyacetone Phosphate and Glyceraldehyde 3-Phosphate for Use in Studies of Fructose-1,6-diphosphate Aldolase Article

Bischofberger, N, Waldmann, H, Saito, T et al. (1988). Synthesis of Analogues of 1,3-Dihydroxyacetone Phosphate and Glyceraldehyde 3-Phosphate for Use in Studies of Fructose-1,6-diphosphate Aldolase . JOURNAL OF ORGANIC CHEMISTRY, 53(15), 3457-3465. 10.1021/jo00250a010

cited authors

  • Bischofberger, N; Waldmann, H; Saito, T; Simon, ES; Lees, W; Bednarski, MD; Whitesides, GM

authors

abstract

  • This paper describes the syntheses of five analogues of dihydroxyacetone phosphate (3-azidohydroxyacetone 1-phosphate (5), 3-(acetylamino)hydroxyacetone 1-phosphate (12), (R)-1,3-dihydroxy-2-butanone 1-phosphate (18), (±)-1,3-dihydroxy-2-butanone 3-phosphate (26), and phosphonomethyl glycolate (31)). The syntheses of 18 and 26 are based on a new reaction: that is, the introduction of the phosphate group by reaction of a diazo ketone with dibenzyl phosphate. These methods provide easy access to a number of compounds that are potential substrates for the synthetically useful enzyme aldolase (fructose-1,6-phosphate aldolase from rabbit muscle, EC 4.1.2.13, RAMA) and perhaps for other enzymes of glycolysis. This paper also describes syntheses of 14 aldehydes for examination as substrates for aldolase. When the precursor was available, ozonolysis of vinyl groups proved to be the best route to the corresponding aldehydes. © 1988, American Chemical Society. All rights reserved.

publication date

  • February 1, 1988

published in

Digital Object Identifier (DOI)

start page

  • 3457

end page

  • 3465

volume

  • 53

issue

  • 15