Synthesis and utilization of a nonhydrolyzable phosphoadenosine phosphosulfate analog.

  title={Synthesis and utilization of a nonhydrolyzable phosphoadenosine phosphosulfate analog.},
  author={K Ng and Mark D'Souza and L Callahan and David H. Geller and A E Kearns and Stephen B. Lyle and Nancy B. Schwartz},
  journal={Analytical biochemistry},
  volume={198 1},
3'-Phosphoadenosine 5'-phosphosulfate (PAPS) functions as the high-energy sulfate donor for sulfate ester synthesis in all higher organisms. This activated sulfate, like its adenosine 5'-phosphosulfate precursor, is both chemically labile and vulnerable to sulfohydrolase degradation. These obstacles have limited the utility of the native PAPS in the purification and mechanistic description of the numerous PAPS-utilizing enzymes. This paper describes the synthesis of the 2'- and 3'-isomers of a… Expand
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Adenosine-5'-O-(2-fluorodiphosphate) (ADPβF), an analog of adenosine-5'-phosphosulfate
Abstract Adenosine-5′-phosphosulfate (APS) and its 3′-phosphorylated metabolite PAPS (3′-phosphoadenosine-5′-phosphosulfate) play central roles in biological systems. Few analogs of APS or PAPS haveExpand
Synthesis of nucleoside phosphosulfates.
Using this method, various NPS with yields ranging from 70-90%, are obtained, including adenosine 5'-phosphosulfate (APS) and 2',3'-cyclic precursor of 3'phosphoadenosine5'-ph phosphate (PAPS), which are the key intermediates in the assimilation and metabolism of sulfur in all living organisms. Expand
Sulfate activation and transport in mammals: system components and mechanisms.
Isolation of the PAPS-synthesizing activities from rat chondrosarcoma and preparation of stable non-hydrolyzable analogs of APS and PAPS have facilitated the kinetic characterization of mammalian ATP sulfurylase and APS kinase. Expand


Synthesis and properties of a nonhydrolyzable adenosine phosphosulfate analog.
This paper describes the simple and efficient synthesis and structural confirmation of a nonhydrolyzable APS analog, beta-methylene APS, with an overall molar yield of 40-50%. Expand
Adenosine 5'-phosphosulfate kinase from Penicillium chrysogenum. Purification and kinetic characterization.
Adenosine 5'-phosphosulfate (APS) kinase, the second enzyme in the pathway of inorganic sulfate assimilation, was purified to near homogeneity from mycelium of the filamentous fungus, PenicilliumExpand
Reconstitution of adenosine 3'-phosphate 5'-phosphosulfate transporter from rat brain.
Specificity of the translocator activity was tested with a number of nucleotide analogues and only 3',5'-adenosine diphosphate was a competitive inhibitor, and inhibitors of the mitochondrial ADP/ATP transporter and the red cell anion channel blocked transport of PAPS only at very high concentrations. Expand
Co-purification and characterization of ATP-sulfurylase and adenosine-5'-phosphosulfate kinase from rat chondrosarcoma.
The two sulfate-activating enzymes, ATP-sulfurylase and adenosine-5'-phosphosulfate kinase, were each purified about 2000-fold from crude rat chondrosarcoma homogenate and consistently co-purified. Expand
The synthesis of oligoribonucleotides. X. Preparation of 2',3'-cyclic phosphates of ribonucleosides and diribonucleoside phosphates via phosphotriester intermediates.
Both 2′,5′-bis-O-4-methoxytetrahydropyran- 4-yluridine o-chlorophenyl ester and phosphotriester derivatives were converted into the corresponding mono- and di-nucleotide phenyl esters by alkaline hydrolysis. Expand
Preparation of adenosine-3'-phosphate-51-phosphosulfate (PAPS): an improved enzymatic method using Chlorella pyrenoidosa.
Adenosine-3′-phosphate-5′- phosphosulfate (PAPS) is prepared from crude French press extracts of the green alga Chlorella pyrenoidosa purified somewhat by high-speed centrifugation and brief dialysis, and sulfate- 35 S is the only detectable radioactive contaminant. Expand
Enzymatic sulfation of steroids. VI. A simple, rapid method for routine enzymatic preparation of 3'-phosphoadenosine-5'-phosphosulfate.
  • S. Singer
  • Chemistry, Medicine
  • Analytical biochemistry
  • 1979
The method uses rat liver as the source of the PAPS synthesizing enzymes, and requires 2 days for production of 98 to 151 μmol of purified coenzyme. Expand
Preparation of adenosine nucleotide derivatives suitable for affinity chromatography.
Examples are given where these derivatives have been successful in reversibly binding dehydrogenases, kinases and myosin and its proteolytic subfragments and the partial purification of rat liver glucokinase on an ADP derivative is shown. Expand
Studies on bovine adrenal estrogen sulfotransferase. III. Facile synthesis of 3'-phospho- and 2'-phosphoadenosine 5'-phosphosulfate.
A practical synthesis of 3'-phosphoadenosine 5'-phosphosulfate (IV) in yields of 68-72% from adenosine 2',3'-cyclic phosphate 5'-phosphate (II) is described. Reaction of II withExpand
Translocation of adenosine 3'-phosphate 5'-phosphosulfate into rat liver Golgi vesicles.
Translocation of PAPS was inhibited following treatment of Golgi vesicles with Pronase under conditions in which the activity of a lumenal Golgi membrane marker such as sialyltransferase was not. Expand