Efficient synthesis and applications of peptides containing adenylylated tyrosine residues

Angewandte Chemie - International Edition

Volumn 50, Issue 39, 2011, Pages 9200-9204

  Smit, Cornelis ^a   Blümer, Julia ^a   Eerland, Martijn F ^a   Albers, Michael F ^a   Müller, Matthias P ^a   Goody, Roger S ^a   Itzen, Aymelt ^a   Hedberg, Christian ^a  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

Author keywords

adenylylation; antibodies; peptides; post translational modifications; Rab proteins

Indexed keywords

ADENYLYLATION; EFFICIENT SYNTHESIS; HUMAN PATHOGENS; LEGIONELLA PNEUMOPHILA; POLYCLONAL ANTIBODY; POST-TRANSLATIONAL MODIFICATIONS; SOLID PHASE PEPTIDE SYNTHESIS; TYROSINE RESIDUES;

AMINO ACIDS; PEPTIDES;

ANTIBODIES;

ADENOSINE PHOSPHATE; BACTERIAL PROTEIN; IMMOBILIZED ANTIBODY; PEPTIDE; PROTEIN CDC42; RAB PROTEIN; TYROSINE;

ANIMAL; ARTICLE; CELL STRAIN COS1; CERCOPITHECUS; CHEMISTRY; ENZYMOLOGY; IMMUNOLOGY; LEGIONELLA PNEUMOPHILA; METABOLISM; PROTEIN PROCESSING; SYNTHESIS; WESTERN BLOTTING;

ADENOSINE MONOPHOSPHATE; ANIMALS; ANTIBODIES, IMMOBILIZED; BACTERIAL PROTEINS; BLOTTING, WESTERN; CDC42 GTP-BINDING PROTEIN; CERCOPITHECUS AETHIOPS; COS CELLS; LEGIONELLA PNEUMOPHILA; PEPTIDES; PROTEIN PROCESSING, POST-TRANSLATIONAL; RAB1 GTP-BINDING PROTEINS; TYROSINE;

EID: 80052864138     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201103203     Document Type: Article

References (19)

1. E. R. Stadtman, J. Biol. Chem. 2001, 276, 44357-44364
2. for a recent review on adenylylation, see, A. Itzen, W. Blankenfeldt, R. S. Goody, Trends Biochem. Sci. 2011, 36, 221-228.
3. M. L. Yarbrough, Y. Li, L. N. Kinch, N. V. Grishin, H. L. Ball, K. Orth, Science 2009, 323, 269-272.
4. M. P. Müller, H. Peters, J. Blümer, W. Blankenfeldt, R. S. Goody, A. Itzen, Science 2010, 329, 946-949.
5. For a recent review covering the topic of small GTPases as regulators of vesicular transport, see, A. Itzen, R. S. Goody, Semin. Cell Dev. Biol. 2011, 22, 48-56.
6. L. N. Kinch, M. L. Yarbrough, K. Orth, N. V. Grishin, PLoS ONE 2009, 4(6), e 5818.
7. Y. H. Hao, T. Chuang, H. L. Ball, P. Luong, Y. Li, R. D. Flores-Saaib, K. Orth, J. Biotechnol. 2011, 151, 251-254.
8. R. A. Al-Eryania, L. Yan, H. L. Ball, Tetrahedron Lett. 2010, 51, 1730-1731.
9. For an early example of interassembly synthesis of adenylylated tyrosine, see, J. A. Todhunter, D. L. Purich, Biochem. Biophys. Res. Commun. 1974, 59, 82-85
10. G. J. van der Heden van Noort, H. S. Overkleeft, G. A. van der Marel, D. V. Filippov, J. Org. Chem. 2010, 75, 5733-5736.
11. H. Ikeuchi, M. E. Meyer, Y. Ding, J. Hiratake, N. G. J. Richards, Bioorg. Med. Chem. 2009, 17, 6641-6650.
12. S. Ficht, R. J. Payne, R. T. Guy, C.-H. Wong, Chem. Eur. J. 2008, 14, 3620-3629; for a previous example of a CNE-phosphoroamidite building block of the Fmoc-protected tyrosine methyl ester, see
13. C. D. Claeboe, R. Gao, S. M. Hecht, Nucl. Acids Res. 2003, 31, 5685-5691.
14. For a recent review on phosphoroamidite chemistry, see, C. Hoebartner, F. Wachowius, Chem. Biol. Nucl. Acids 2010, 1-37.
15. M. Dessolin, M. G. Guillerrez, N. Thieriet, F. Guibe, A. Loffet, Tetrahedron Lett. 1995, 36, 5741.
16. V. Dourtoglou, B. Gross, V. Lambropoulou, C. Ziodrou, Synthesis 1984, 572.
17. L. A. Carpino, J. Am. Chem. Soc. 1993, 115, 4397.
18. Peptide conjugation, immunization, and antibody purification were performed by Biogenes GmBH, Berlin, Germany (www.biogenes.de).
19. D. V. Palanivelu, A. Goepfert, M. Meury, P. Guye, C. Dehio, T. Schirmer, Protein Sci. 2011 20, 492-499.