Gram scale synthesis of 3-fluoro-1-hydroxyacetone phosphate: a novel donor substrate in rabbit muscle aldolase-catalyzed aldol reactions.

@article{Fischer2011GramSS,
  title={Gram scale synthesis of 3-fluoro-1-hydroxyacetone phosphate: a novel donor substrate in rabbit muscle aldolase-catalyzed aldol reactions.},
  author={M. Fischer and H. Kaehlig and W. Schmid},
  journal={Chemical communications},
  year={2011},
  volume={47 23},
  pages={
          6647-9
        }
}
  • M. Fischer, H. Kaehlig, W. Schmid
  • Published 2011
  • Chemistry, Medicine
  • Chemical communications
    • An efficient gram scale synthesis of 3-fluoro-1-hydroxyacetone phosphate (FHAP) has been developed. As a close analog to dihydroxyacetone phosphate, FHAP was used as a novel donor substrate for rabbit muscle aldolase catalyzed reactions. The different binding affinities of the gem-diol and keto form of FHAP were studied by (19)F-NMR. 
    View PDF
    4 Citations
    Background Citations
    1
    4 Citations
    Citation Type

    Citation Type

    Decarboxylative Cascade Reactions of Dihydroxyfumaric Acid: A Preparative Approach to the Glyoxylate Scenario.
    • 2
    Stereoselective Aldol Reaction in Aqueous Solution Using Prolinamido-Glycosides as Water-Compatible Organocatalyst
    • 3
    • PDF
    6.12 Inorganic Acid Derivatives
    Gram Scale Synthesis of 3-Fluoro-1-hydroxyacetone Phosphate: A Novel Donor Substrate in Rabbit Muscle Aldolase-Catalyzed Aldol Reactions.

    References

    SHOWING 1-10 OF 53 REFERENCES
    Practical synthesis of 4-hydroxy-3-oxobutylphosphonic acid and its evaluation as a bio-isosteric substrate of DHAP aldolase.
    • 19
    Enzymes as reagents in organic chemistry : transketolase-catalysed synthesis of D-[1,2-13C2]xylulose
    • 34
    Effects of chirality and substituents at carbon 3 in dihydroxyacetone-phosphate analogues on their binding to rabbit muscle aldolase.
    • 10
    Indium‐Mediated Allenylation of Aldehydes and Its Application in Carbohydrate Chemistry: Efficient Synthesis of D‐Ribulose and 1‐Deoxy‐D‐ribulose
    • 9
    SYNTHESIS OF ANALOGS OF 1,3-DIHYDROXYACETONE PHOSPHATE AND GLYCERALDEHYDE-3-PHOSPHATE FOR USE IN STUDIES OF FRUCTOSE-1,6-DIPHOSPHATE ALDOLASE
    • 68
    Synthesis of phosphono analogues of dihydroxyacetone phosphate and glyceraldehyde 3-phosphate.
    • 18
    Synthesis and evaluation of 1-deoxy-D-xylulose 5-phosphoric acid analogues as alternate substrates for methylerythritol phosphate synthase.
    • 40
    Dihydroxyacetone phosphate. Its structure and reactivity with -glycerophosphate dehydrogenase, aldolase and triose phosphate isomerase and some possible metabolic implications.
    • 99
    Properties of the phosphonomethyl isosteres of two phosphate ester glycolytic intermediates.
    • 22
    • PDF
    Synthesis of sugars by aldolase-catalyzed condensation reactions
    • 102
    • PDF