The H-bonding network of acylguanidine complexes: Combined intermolecular 2hJH,P and 3hJN,P scalar couplings provide an insight into the geometric arrangement

Journal of the American Chemical Society

Volumn 130, Issue 50, 2008, Pages 16846-16847

  Federwisch, Guido ^a   Kleinmaier, Roland ^a   Drettwan, Diana ^a   Gschwind, Ruth M ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLGUANIDINE DERIVATIVE; AMIDE; AMINOTRANSFERASE; BISPHOSPHONIC ACID DERIVATIVE; G PROTEIN COUPLED RECEPTOR; GUANIDINE DERIVATIVE; ORGANIC SOLVENT; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENZYME ACTIVITY; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; SIGNAL TRANSDUCTION;

ACYLATION; GUANIDINE; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 58049213987     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807042u     Document Type: Article

References (25)

1. (a) Alkorta, I.; Elguero, J.; Denisov, G. S. Magn. Reson. Chem. 2008, 46, 599-624.
2. (b) Dingley, A. J.; Cordier, F.; Jaravine, V. A.; Grzesiek, S. In BioNMR in Drug Research; Zerbe, O., Ed.; Wiley-VCH: Weinheim, Germany, 2003.
3. (c) Grzesiek, S.; Cordier, F.; Jaravine, V.; Barfield, M. Prog. Magn. Reson. Spectrosc. 2004, 45, 275-300.
4. Sharif, S.; Fogle, E.; Toney, M. D.; Denisov, G. S.; Shenderovich, I.; Buntkowsky, G.; Tolstoy, P. M.; Huot, M. C.; Limbach, H.-H. J. Am. Chem. Soc. 2007, 129, 9558-9559.
5. (a) Löhr, F.; Mayhew, S. G.; Rüterjans, H. J. Am. Chem. Soc. 2000, 122, 9289-9295.
6. (b) Mishima, M.; Hatanaka, M.; Yokoyama, S.; Ikegami, T.; Wälchli, M.; Ito, Y.; Shirakawa, M. J. Am. Chem. Soc. 2000, 122, 5883-5884.
7. (c) Liu, A.; Majumdar, A.; Jiang, F.; Chernichenko, N.; Skriptin, E.; Patel, D. J. J. Am. Chem. Soc. 2000, 122, 11226-11227.
8. Gschwind, R. M.; Armbrüster, M.; Zubrzycki, I. J. Am. Chem. Soc. 2004, 126, 10228-10229.
9. (a) Katritzky, A. R.; Rogovoy, B. V.; Cai, X.; Kirichenko, N.; Kovalenko, K. V. J. Org. Chem. 2004, 69, 309-313, and references therein.
10. (b) Lee, S.; Kim, T.; Lee, B. H.; Yoo, S.; Lee, K.; Yi, K. Y. Bioorg. Med. Chem. Lett. 2007, 17, 1291-1295.
11. (c) Cole, D. C.; et al. J. Bioorg. Med. Chem. Lett. 2008, 18, 1063-1066.
12. (a) Ghorai, P.; Kraus, A.; Keller, M.; Götte, C.; Igel, P.; Schneider, E.; Schnell, D.; Bernhardt, G.; Dove, S.; Zabel, M.; Elz, S.; Seifert, R.; Buschauer, A. J. Med. Chem. and references therein. In press.
13. (b) Keller, M.; Pop, N.; Hutzler, C.; Beck-Sickinger, A. G.; Bernhardt, G.; Buschauer, A. J. Med. Chem. In press.
14. (c) Schneider, E.; Keller, M.; Brennauer, A.; Hoefelschweiger, B. K.; Gross, D.; Wolfbeis, O. S.; Bernhardt, G.; Buschauer, A. ChemBioChem 2007, 8, 1981-1988.
15. Schrader, T. Chem. Eur. J. 1997, 3, 1537-1541.
16. (a) Tate, S.; Kubo, Y.; Ono, A.; Kainosho, M. J. Am. Chem. Soc. 1995, 117, 7277-7278.
17. (b) Vuister, G.; Bax, A. J. Am. Chem. Soc. 1993, 115, 7772-7777.
18. Kleinmaier, R.; Gschwind, R. M. J. Label Compd. Radiopharm. In press.
19. Cordier, F.; Grzesiek, S. J. Am. Chem. Soc. 1999, 121, 1601-1602.
20. (a) Czernek, J.; Brueschweiler, R. J. Am. Chem. Soc. 2001, 123, 11079-11080.
21. (b) Alkorta, I.; Elguero, J.; Del Bene, J. E. Chem. Phys. Lett. 2005, 412, 97-100.
22. (c) Del Bene, J. E.; Perera, S. A.; Bartlett, R. J.; Elguero, J.; Alkorta, I.; Lopez-Leonardo, C.; Alajarin, M. J. Am. Chem. Soc. 2002, 124, 6393-6397.
23. Luy, B.; Marino, J. P. J. Am. Chem. Soc. 2000, 122, 8095-8096.
24. Markwick, P. R. L.; Sprangers, R.; Sattler, M. J. Am. Chem. Soc. 2003, 125, 644-645.
25. Schlund, S.; Schmuck, C.; Engels, B. Chem. Eur. J. 2007, 13, 6644-6653.