N-terminal protein modification through a biomimetic transamination reaction (Angewandte Chemie - International Edition (2006) 45, (5307-5311) DOI: 10.1002/anie.200600368);N-terminal protein modification through a biomimetic transamination reaction

Angewandte Chemie - International Edition

Volumn 45, Issue 32, 2006, Pages 5307-5311

  Gilmore, Joshua M ^a,b   Scheck, Rebecca A ^a,b   Esser Kahn, Aaron P ^a,b   Joshi, Neel S ^a,b   Francis, Matthew B ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

Bioconjugation; Bioorganic chemistry; Oximes; Protein modifications

Indexed keywords

AMINO ACIDS; CHEMICAL MODIFICATION; NITROGEN COMPOUNDS; PHOSPHATES;

BIOCONJUGATION; BIOORGANIC CHEMISTRY; OXIMES; PROTEIN MODIFICATIONS;

PROTEINS;

EID: 33747880302     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200890204     Document Type: Erratum

References (29)

1. For an excellent review on protein bioconjugation, see: G. T. Hermanson, Bioconjugate Techniques, 1st ed., Academic Press, San Diego, 1996.
2. R. F. Doolittle in Prediction of Protein Structure and the Principles of Protein Conformation (Ed.: G. D. Fasman), Plenum, New York, 1989.
3. a) J. M. Antos, M. B. Francis, J. Am. Chem. Soc. 2004, 126, 10256;
4. b) N. S. Joshi, L. R. Whitaker, M. B. Francis, J. Am. Chem. Soc. 2004, 126, 15924;
5. c) J. M. Hooker, E. W. Kovacs, M. B. Francis, J. Am. Chem. Soc. 2004, 126, 3718-3719;
6. d) S. D. Tilley, M. B. Francis, J. Am. Chem. Soc. 2006, 128, 1080-1081.
7. D. P. Baker, E. Y. Lin, K. Lin, M. Pellegrini, R. C. Petter, L. L. Chen, R. M. Arduini, M. Brickelmaier, D. Wen, D. M. Hess, L. Chen, D. Grant, A. Whitty, A. Gill, D. J. Lindner, R. B. Pepinsky, Bioconj. Chem. 2006, 17(1), 179-188.
8. a) P. E. Dawson, T. W. Muir, I. Clarklewis, S. B. H. Kent, Science 1994, 266, 776-779;
9. b) T. W. Muir, Annu. Rev. Biochem. 2003, 72, 249-289.
10. J. P. Tam, Q. Yu, Z. Miao, Biopolymers 1999, 51, 311-332.
11. a) K. F. Geoghegan, J. G. Stroh, Bioconjugate Chem. 1992, 3, 138-146;
12. b) J. K. Chen, W. S. Lane, A. W. Brauer, A. Tanaka, S. L. Schreiber, J. Am. Chem. Soc. 1993, 115, 12591-12592.
13. X. Li, L. Zhang, S. E. Hall, J. P. Tam, Tetrahedron Lett. 2000, 41, 4069-4073.
14. H. B. F. Dixon, J. Protein Chem. 1984, 3, 99-108.
15. W. P. Jencks, J. Am. Chem. Soc. 1959, 81, 475-481.
16. R. Fields, H. B. F. Dixon, Methods Enzymol. 1972, 25, 409-419.
17. See the Supporting Information for details.
18. For reviews of PLP-mediated reactions, see: a) M. D. Toney, Arch. Biochem. Biophys, 2005, 433, 279-287;
19. b) A. C. Eliot, J. F. Kirsch, Annu. Rev. Biochem. 2004, 73, 383-415.
20. a) M. Calzadilla, T. Cordova, A. Malpica, J. Phys. Org. Chem. 1999, 12, 708-712;
21. b) S. Rosenberg, S. M. Silver, J. M. Sayer, W. P. Jencks, J. Am. Chem. Soc. 1974, 96, 7987;
22. see also: c) H. C. Hang, C. R. Bertozzi, Acc. Chem. Res. 2001, 34, 727-736;
23. d) V. W. Cornish, K. M. Hahn, P. G. Schultz, J. Am. Chem. Soc. 1996, 118, 8150-8151.
24. R. Y. Tsien, Annu. Rev. Biochem. 1998, 67, 509-544.
25. R. E. Offord, H. F. Gaertner, Bioconjugate Chem. 1996, 7, 38-44.
26. For an avidin/biotin-based approach to the site-selective attachment of polymers to proteins, see: D. Bontempo, H. D. Maynard, J. Am. Chem. Soc. 2005, 127, 6508-6509.
27. For an alternate strategy that employs solid-phase-assisted synthesis to yield an aminooxy-functionalized protein which has also been used to prepare PEG monoconjugates, see: H. Shao, M. M. Crnogorac, T. Kong, S.-Y. Chen, J. M. Williams, J. M. Tack, V. Gueriguian, E. N. Cagle, M. Carnevali, D. Tumelty, X. Paliard, L. P. Miranda, J. A. Bradburne, G. G. Kochendoerfer, J. Am. Chem. Soc. 2005, 127, 1350-1351;
28. see also: G. G. Kochendoerfer, Curr. Opin. Chem. Biol. 2005, 9, 555-560.
29. T. L. Schlick, Z. Ding, E. W. Kovacs, M. B. Francis, J. Am. Chem. Soc. 2005, 127, 3718-3723.