Highly efficient solid-phase phosphopeptide synthesis using bis-(polyfluorophenyl) chlorophosphates: Preparation of serine-threonine protein phosphatase substrates

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8227-8230

  Hormozdiari, Pantea ^a   Gani, David ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; ENZYME SUBSTRATE; PROTEIN SYNTHESIS; TECHNIQUE;

EID: 0030569269     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01874-6     Document Type: Article

References (15)

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4. 3. Goldberg, J.; Huang, H-B.; Kwon, Y-G.; Greengard, P.; Nairn, A. C.; Kuriyan, J. Nature, 1995, 376, 745.
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6. 5. a) Donella-Deana, A.; Mac Gowan, C. H.; Cohen, P.; Marchiori, F.; Meyer, H. E.; Pinna, L. A. Biochim. Biophys. Acta, 1990, 1051, 199;
7. b) Pinna, L. A.; Agostinis, P.; Donella-Deana, A.; Marchiori, F. Adv. Prot. Phosphatases, 1989, 5, 51.
8. 6. Paquet, A.; Johns, M. Int. J. Peptide Protein Res., 1990, 36, 97.
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11. 9. Schulz, J.; Wilkie, J.; Lightfoot, P.; Rutherford, T.; Gani, D. J. Chem. Soc. Chem. Commun., 1995, 2353.
12. 10. The large increase in the rates of acid-catalysed hydrolysis for the pentafluorophenyl and tetrafluorophenyl phosphate triesters compared to those for the non-fluorinated analogues, may be accounted for by their abilities to chelate a proton, possibly through an onrtho-fluorine atom and the phenol phosphate O-atom, to enhance the electrophilicity of the phosphorus atom. The acid lability of bis-perfluorophenyl phosphate triesters [prepared from reagent (7)] has been noted previously. a) Boschan, R. H.; Holder, J. P. U.S. Patent Office 3,341,630, 1967;
13. b) Podolskii, A. V.; Bulatov, M. A. Chem Abs., 1976, 85, 32557h. Details on the kinetics of the phosphorylation and deprotection chemistry will be reported elsewhere.
14. 11. King, D. S.; Fields, C. G.; Fields, G. B. Int. J. Peptide Protein Res., 1990, 36, 255.
15. 12. Mehrotra, A. P.; Gani, D. Tet. Lett., 1996, 37, 6915.