A variety of phosphonates (XPO32-; X = H-, CH3-, CL3C-, CH3CH2-, and phenyl-) as well as methylarsonate have been shown to be suitable phosphate analogs for the reactions catalyzed by yeast glyceraldehyde-3-phosphate dehydrogenase and calf spleen purine nucleoside phosphorylase. The reactivity of the phosphate analogs with these two enzymes is independent of the pKa of the analog.
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Gardner et al. (1977) studied this question.
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