Conjugation of a novel histidine derivative to biomolecules and labelling with [99mTc(OH2)3(CO)3]+

Organic and Biomolecular Chemistry

Volumn 2, Issue 18, 2004, Pages 2593-2603

  Van Staveren, Dave R ^a   Mundwiler, Stefan ^a   Hoffmanns, Ulrich ^b   Pak, Jae Kyoung ^a   Spingler, Bernhard ^a   Metzler Nolte, Nils ^b   Alberto, Roger ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; AMINES; CARBOXYLIC ACIDS; COORDINATION REACTIONS; GAMMA RAYS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ORGANOMETALLICS; OXIDATION; REACTION KINETICS; RHENIUM COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); THERMODYNAMICS; VITAMINS;

COUPLING REAGENTS; OXIDATION STATES; REACTION TIMES; RETENTION TIMES;

ORGANIC COMPOUNDS;

BIOTIN; CYANOCOBALAMIN; DRUG DERIVATIVE; HISTIDINE; LEUCINE ENKEPHALIN; TECHNETIUM COMPLEX;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOTOPE LABELING; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BIOTIN; CRYSTALLOGRAPHY, X-RAY; ENKEPHALIN, LEUCINE; HISTIDINE; ISOTOPE LABELING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOTECHNETIUM COMPOUNDS; VITAMIN B 12;

EID: 4744339937     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b405575f     Document Type: Article

References (37)

1. J. R. Dilworth and S. J. Parrott, Chem. Soc. Rev., 1998, 27, 43-55.
2. S. S. Jurisson and J. D. Lydon, Chem. Rev., 1999, 99, 2205-2218.
3. H. F. Kung, M. P. Kung and S. R. Choi, Semin. Nucl. Med., 2003, 33, 2-13.
4. S. Liu and D. S. Edwards, Chem. Rev., 1999, 99, 2235-2268.
5. R. Alberto, Eur. J. Nucl. Med. Mol. Imaging, 2003, 30, 1299-1302.
6. R. Schibli, R. L. Bella, R. Alberto, E. Garcia-Garayoa, K. Ortner, U. Abram and P. A. Schubiger, Bioconjugate Chem., 2000, 3, 345-351.
7. R. Schibli, R. Schwarzbach, R. Alberto, K. Ortner, H. Schmalle, C. Dumas, A. Egli and P. A. Schubiger, Bioconjugate Chem., 2002, 13, 750-756.
8. A. Egli, R. Alberto, L. Tannahill, R. Schibli, U. Abram, A. Schaffland, R. Waibel, D. Tourwe, L. Jeannin, K. Iterbeke and P. A. Schubiger, J. Nucl. Med., 1999, 40, 1913-1917.
9. S. Seifert, J. U. Kunstler, A. Gupta, H. Funke, T. Reich, H. E. Pietzsch, R. Alberto and B. Johannsen, Inorg. Chim. Acta, 2001, 322, 79-86.
10. J. D. G. Correia, A. Domingos, I. Santos, R. Alberto and K. Ortner, Inorg. Chem., 2001, 40, 5147-5151.
11. R. Alberto, R. Schibli, A. Egli, U. Abram, T. A. Kaden and P.A. Schubiger, J. Am. Chem. Soc., 1998, 120, 7987.
12. D. R. van Staveren, E. Bothe, T. Weyhermuller and N. Metzler-Nolte, Chem. Commun., 2001, 131-132.
13. D. R. van Staveren, E. Bill, E. Bothe, M. Buhl, T. Weyhermuller and N. Metzler-Nolte, Chem. Eur. J., 2002, 8, 1649-1662.
14. D. R. van Staveren and N. Metzler-Nolte, Chem. Commun., 2002, 1406-1407.
15. D. R. van Staveren, E. Bothe and N. Metzler-Nolte, Organometallics, 2003, 22, 3102-3106.
16. J. K. Pak, P. Benny, B. Spingler, K. Ortner and R. Alberto, Chem. Eur. J., 2003, 9, 2053-2061.
17. M. Bodansky and A. Bodansky, The Practice of Peptide Synthesis, Springer-Verlag, Berlin, 1984.
18. M. Bodansky, Principles of Peptide Synthesis, Springer-Verlag, Berlin, 1984.
19. J. Jones, The Chemical Synthesis of Peptides, Clarendon Press, Oxford, 1991.
20. T. W. Greene and P. G. M. Wuts, Protective groups in organic synthesis, John Wiley & Sons, New York, 1999.
21. J. Hughes, T. W. Smith, H. W. Kosterlitz, L. A. Fothergill, B. A. Morgan and H. R. Morris, Nature, 1975, 258, 577-579.
22. S. Udenfried and J. Meienhofer, in The Peptides: Analysis, Synthesis, Biology, Academic Press, New York, 1984, vol. 6, p. 324-389.
23. Vitamin B12 and B12-Proteins, ed. B. Kräutler, D. Arigoni, and B. T. Golding, Wiley-VCH, Weinheim, 1998.
24. Chemistry and Biochemistry of B12, ed. R. Banerjee, Wiley, New York, 1999.
25. P. M. Pathare, D. S. Wilbur, S. Heusser, E. V. Quadros, P. McLoughlin and A. C. Morgan, Bioconjugate Chem., 1996, 7, 217-232.
26. J. B. Armitage, J. R. Cannon, A. W. Johnson, L. F. J. Parker, E. L. Smith, W. H. Stafford and A. R. Todd, J. Chem. Soc., 1953, 3849-3864.
27. K. Bernhauer, H. Vogelmann and F. Wagner, Hoppe-Seyler's Z. Physiol. Chem., 1968, 349, 1281.
28. R. Alberto, R. Schibli, A. P. Schubiger, U. Abram, H. J. Pietzsch and B. Johannsen, J. Am. Chem. Soc., 1999, 121, 6076-6077.
29. R. Alberto, K. Ortner, N. Wheatley, R. Schibli and A. P. Schubiger, J. Am. Chem. Soc., 2001, 123, 3135-3136.
30. R. Jain and L. A. Cohen, Tetrahedron, 1996, 52, 5363-5370.
31. H. Harada, O. Asano, T. Kawata, T. Inoue, T. Horizoe, N. Yasuda, K. Nagata, M. Murakami, J. Nagaoka, S. Kobayashi, I. Tanaka and S. Abe, Bioorg. Med. Chem., 2001, 9, 2709-2726.
32. C. Hunter, R. F. W. Jackson and H. K. Rami, J. Chem. Soc., Perkin Trans. 1, 2000, 219-223.
33. M. Maltese, J. Org. Chem., 2001, 66, 7615-7625.
34. A. J. Brouwer, S. J. E. Mulders and R. M. J. Liskamp, Eur. J. Org. Chem., 2001, 1903-1915.
35. H. J. Meder and W. Beck, Z Naturforsch. B, 1986, 41, 1247-1254.
36. R. Alberto, A. Egli, U. Abram, K. Hegetschweiler, V. Gramlich and P. A. Schubiger, J. Chem. Soc., Dalton Trans., 1994, 2815-2820.
37. D. Jönsson and A. Undén, Tetrahedron Lett., 2002, 43, 3125-3328.