Enantiodivergence in small-molecule catalysis of asymmetric phosphorylation: Concise total syntheses of the enantiomeric D-myo-inositol-1-phosphate and D-myo-inositol-3-phosphate

Journal of the American Chemical Society

Volumn 124, Issue 39, 2002, Pages 11653-11656

  Sculimbrene, Bianca R ^a   Morgan, Adam J ^a   Miller, Scott J ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHORYLATION;

CATALYSTS; PHOSPHATES; SYNTHESIS (CHEMICAL);

CATALYSIS;

INOSITOL 3 PHOSPHATE; INOSITOL PHOSPHATE; PEPTIDE LIBRARY; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; ENANTIOMER; MOLECULE; PEPTIDE ANALYSIS; PHOSPHORYLATION; STEREOCHEMISTRY;

CATALYSIS; INOSITOL PHOSPHATES; KINETICS; OLIGOPEPTIDES; PHOSPHORYLATION; STEREOISOMERISM;

EID: 0037010024     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027402m     Document Type: Article

References (35)

1. For reviews on asymmetric catalysis, see: Comprehensive Asymmetric Catalysis, Vols. I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, Germany, 1999.
2. For an excellent review of enantiodivergence in asymmetric synthesis, see: Sibi, M. P.; Liu, M. Curr. Org. Chem. 2001, 5, 719.
3. For a synthetic example, see: Milton, R. C. L.; Milton, S. C. F.; Kent, S. B. H. Science 1992, 256, 1445.
4. (a) For a "Directed Evolution" approach to modified enzymes with reversed enantioselectivity, see: Zha, D.; Wilensek, S.; Hermes, M.; Jaeger, K.-E.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 2001, 2664.
5. (b) See also: Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier Science Ltd.: Oxford, U.K., 1994.
6. Acylation: (a) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (b) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Azidation: (c) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (d) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635.
7. Acylation: (a) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (b) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Azidation: (c) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (d) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635.
8. Acylation: (a) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (b) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Azidation: (c) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (d) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635.
9. Acylation: (a) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (b) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Azidation: (c) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134. (d) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635.
10. For other representative metal-free peptide and peptide-like enantioselective catalysts, see: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901. (b) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910. (c) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481.
11. For other representative metal-free peptide and peptide-like enantioselective catalysts, see: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.(b) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910. (c) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481.
12. For other representative metal-free peptide and peptide-like enantioselective catalysts, see: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.(b) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910. (c) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481.
13. (a) Agranoff, B. W.; Fisher, S. K. In Inositol Phosphates and Derivatives: Synthesis, Biochemistry and Therapeutic Potential; Reitz, A. B., Ed.; ACS Symposium Series 463; American Chemical Society: Washington, DC, 1991; p 20.
14. (b) Billington, D. C. The Inositol Phosphates: Chemical Synthesis and Biological Significance; VCH: New York, 1993.
15. We have observed enantiodivergent peptide catalysis for acyl transfer. See: Copeland, G. T.; Jarvo, E, R.; Miller, S. J. J. Org. Chem. 1998, 63, 6784.
16. There are often advantages to employing enzymes in organic solvents also. See: Klibanov, A. M. Nature 2001, 409, 241-246.
17. Sculimbrene, B. R.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 10125.
18. For the spectroscopic observation of the NMI-DPCP adduct, see: Mal'tseva, T. V.; Ivanova, E. M.; Korobeinicheva, I. K. Izv. Sib. Otd. Akad. Nauk. SSSR, Ser. Khim. Nauk. 1985, 112-116.
19. Pirrung, M. C. Chem. Biol. 1999, 6, R167.
20. For several examples of His-dependent kinases, see: (a) Bilwes, A. M.; Alex, L. A.; Crane, B. R.; Simon, M. I. Cell 1999, 96, 131. (b) Mizuguchi, H.; Cook, P. F.; Tai, C. H.; Hasemann, C. A.; Uyeda, K. J. Biol. Chem. 1999, 274, 2166. (c) Fraser, M. E.; James, M. N.; Bridger, W. A.; Wolodko, W. T. J. Mol. Biol. 1999, 285, 1633.
21. For several examples of His-dependent kinases, see: (a) Bilwes, A. M.; Alex, L. A.; Crane, B. R.; Simon, M. I. Cell 1999, 96, 131. (b) Mizuguchi, H.; Cook, P. F.; Tai, C. H.; Hasemann, C. A.; Uyeda, K. J. Biol. Chem. 1999, 274, 2166. (c) Fraser, M. E.; James, M. N.; Bridger, W. A.; Wolodko, W. T. J. Mol. Biol. 1999, 285, 1633.
22. For several examples of His-dependent kinases, see: (a) Bilwes, A. M.; Alex, L. A.; Crane, B. R.; Simon, M. I. Cell 1999, 96, 131. (b) Mizuguchi, H.; Cook, P. F.; Tai, C. H.; Hasemann, C. A.; Uyeda, K. J. Biol. Chem. 1999, 274, 2166. (c) Fraser, M. E.; James, M. N.; Bridger, W. A.; Wolodko, W. T. J. Mol. Biol. 1999, 285, 1633.
23. (a) Gellman, S. H. Curr. Opin. Chem. Biol. 1998, 2, 717.
24. (b) Venkatraman, J.; Shankaramma, S. C.; Balaram, P. Chem. Rev. 2001, 101, 3131.
25. β-Turns and β-hairpins have been found to exhibit enantioselectivity in a number of other catalytic processes. For example, see: (a) Reference 5. (b) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522.
26. β-Turns and β-hairpins have been found to exhibit enantioselectivity in a number of other catalytic processes. For example, see:(a) Reference 5. (b) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522.
27. (a) Urbaniak, G. C.; Plous, S. Research Randomizer, version 2.1 [Internet-based computer program]; Middletown, CT. Retrieved most recently June 19, 2002, from http://www.randomizer.org.(b) The library was initially prepared to screen asymmetric acylations. See: Jarvo. E. R.; Evans, C. A.; Copeland, G. T.; Miller, S. J. J. Org. Chem. 2001, 66, 5522.
28. (a) Urbaniak, G. C.; Plous, S. Research Randomizer, version 2.1 [Internet-based computer program]; Middletown, CT. Retrieved most recently June 19, 2002, from http://www.randomizer.org.(b) The library was initially prepared to screen asymmetric acylations. See: Jarvo. E. R.; Evans, C. A.; Copeland, G. T.; Miller, S. J. J. Org. Chem. 2001, 66, 5522.
29. A comprehensive list of the sequences and the screening results are provided in the Supporting Information.
30. The extent to which the bis(phosphorylated) product is formed serves as a correction mechanism for enantioselectivity. See: Schreiber, S. L.; Schreiber, T. S.; Smith, D. B. J. Am. Chem. Soc. 1987, 109, 1525.
31. For reviews of enantioselective desymmetrization, see: (a) Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9.(b) Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765.
32. For reviews of enantioselective desymmetrization, see: (a) Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9.(b) Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765.
33. Billington, D. C.; Baker, R.; Kulagowski, J. J.; Mawer, J. M. J. Chem. Soc., Chem. Commun. 1987, 314.
34. Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975.
35. Gani, D. Nature 2001, 414, 703.