113474-78-5Relevant articles and documents
Biosynthesis of Natural Products with a P-C Bond, I. - Incorporation of D-Glucose into (2-Aminoethyl)phosphonic Acid in Tetrahymena thermophila
Hammerschmidt, Friedrich
, p. 531 - 536 (2007/10/02)
The phosphate-phosphonate rearrangement is tested as a model reaction for the biosynthesis of the P-C bond as alternative to the rearrangement of phosphoenolpyruvate.D-glucose was prepared and added to the growth medium of Tetrahymena thermophila. (2-Aminoethyl)phosphonic acid (AEP) (1) was isolated from the wet cell mass by hydrolysis with 6N HCl and ion exchange chromatography and was derivatized to the crystalline 4-bromobenzamide 26.The amount of -AEP in admixture with unlabeled AEP was up to 43percent, which is not in agreement with an enzymic phosphate-phosphonate rearrangement of dihydroxyacetone phosphate, for which monodeutereated AEP would be expected.For comparison -AEP (31) was prepared starting from 2-amino-ethanol.