Download PDF
Synthesis 2009(22): 3765-3768  
DOI: 10.1055/s-0029-1217025
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Incorporation of a Phosphatase Activity-Dependent Quinone Methide Generating Motif into Phosphotyrosine

Kui Shen*, Lixin Qi, Mohini Ravula
Northern Illinois University, Department of Chemistry and Biochemistry, DeKalb, IL 60115, USA
Fax: +1(815)7534802; e-Mail: kshen@niu.edu;
Further Information

Publication History

Received 23 April 2009
Publication Date:
23 September 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

A novel phosphotyrosine analogue that incorporates a phosphatase activity-dependent quinone methide generating motif is synthesized from tyrosine. Following orthoformylation of the phenol moiety of methyl N-Cbz-tyrosinate, the Fmoc-protected 3-difluoromethyl analogue of phosphotyrosine is obtained by functional group transformations.

Key words

amino acids - fluorine - hydrolyses - phosphates - quinone methides - quinomethanes

    References

  • 1a Hunter T. Cell  2000,  100:  113 
    Google Scholar
  • 1b Julien SG. Dube N. Read M. Penney J. Paquet M. Han Y. Kennedy BP. Muller WJ. Tremblay ML. Nature Genetics  2007,  39:  338 
    Google Scholar
  • 1c Saha S. Bardelli A. Buckhaults P. Velculescu VE. Rago C. St. Croix B. Romans KE. Choti MA. Lengauer C. Kinzler KW. Vogelstein B. Science  2001,  294:  1343 
    Google Scholar
  • 1d Zeng Q. Dong JM. Guo K. Li J. Tan HX. Koh V. Pallen CJ. Manser E. Hong W. Cancer Res.  2003,  63:  2716 
    Google Scholar
  • 1e Alonso A. Sasin J. Bottini N. Friedberg I. Friedberg I. Osterman A. Godzik A. Hunter T. Dixon J. Mustelin T. Cell  2004,  117:  699 
    Google Scholar
  • 2a Blanchetot C. Chagnon M. Dube N. Halle M. Tremblay ML. Methods  2005,  35:  44 
    Google Scholar
  • 2b Zhang X. Guo A. Yu J. Possemato A. Chen Y. Zheng W. Polakiewicz RD. Kinzler KW. Vogelstein B. Velculescu VE. Wang ZJ. Proc. Natl. Acad. Sci. U.S.A.  2007,  104:  4060 
    Google Scholar
  • 3a Cravatt BF. Wright AT. Kozarich JW. Annu. Rev. Biochem.  2008,  77:  383 
    Google Scholar
  • 3b Luo Y. Knuckley B. Bhatia M. Thompson PR. J. Am. Chem. Soc.  2006,  128:  1092 
    Google Scholar
  • 4 Shen K. Qi L. Ravula M. Klimaszewski K. Bioorg. Med. Chem. Lett.  2009,  19:  3264 
    CrossrefGoogle Scholar
  • 5a Myers JK. Widlanski TS. Science  1993,  262:  1451 
    Google Scholar
  • 5b Wang Q. Dechert U. Jirik F. Withers SG. Biochem. Biophys. Res. Commun.  1994,  200:  577 
    Google Scholar
  • 5c Born TL. Myers JK. Widlanski TS. Rusnak F. J. Biol. Chem.  1995,  270:  25651 
    Google Scholar
  • 5d Bolton JL. Turnipseed SB. Thompson JA. Chem.-Biol. Interact.  1997,  107:  185 
    Google Scholar
  • 5e Betley JR. Cesaro-Tadic S. Mekhalfia A. Rickard JH. Denham H. Partridge LJ. Plückthun A. Blackburn GM. Angew. Chem. Int. Ed.  2002,  41:  775 
    Google Scholar
  • 5f Zhu Q. Huang X. Chen GYJ. Yao SQ. Tetrahedron Lett.  2003,  44:  2669 
    Google Scholar
  • 5g Lo L.-C. Chiang Y.-L. Kuo C.-H. Liao H.-K. Chen Y.-J. Lin J.-J. Biochem. Biophys. Res. Commun.  2004,  326:  30 
    Google Scholar
  • 6a Williams RM. Im M.-N. J. Am. Chem. Soc.  1991,  113:  9276 
    Google Scholar
  • 6b Smyth MS. Burke TR. Org. Prep. Proced. Int.  1996,  28:  77 
    Google Scholar
  • 6c Hubbard CE. Barrios AM. Bioorg. Med. Chem. Lett.  2008,  18:  679 
    Google Scholar
  • 7a Dhawan B. Redmore D. J. Org. Chem.  1984,  49:  4018 
    Google Scholar
  • 7b Dhawan B. Redmore D. J. Org. Chem.  1986,  51:  179 
    Google Scholar
  • 7c Tian Z. Gu C. Roeske RW. Zhou M. Van Ettan RL. Int. J. Pept. Protein Res.  1993,  42:  155 
    Google Scholar
  • 7d Wakamiya T. Nishida T. Togashi R. Saruta K. Yasuoka J. Kusumoto S. Bull. Chem. Soc. Jpn.  1996,  69:  465 
    Google Scholar
  • 8a Hansen TV. Skattebøl L. Org Synth.  2005,  82:  64 
    Google Scholar
  • 8b Hofsløkken NU. Skattebøl L. Acta Chem. Scand.  1999,  53:  258 
    Google Scholar
  • 9 Rachele JR. J. Org. Chem.  1963,  28:  2898 
    Google Scholar
  • 10a Smyth MS. Burke TR. Tetrahedron Lett.  1994,  35:  551 
    Google Scholar
  • 10b Schwarzer D. Zhang Z. Zheng W. Cole PA. J. Am. Chem. Soc.  2006,  128:  4192 
    Google Scholar
  • 11 Pascal R. Sola R. Tetrahedron Lett.  1998,  39:  503l 
    Google Scholar
  • 12 Shen K. Methods  2007,  42:  234 
    CrossrefGoogle Scholar