First synthesis and determination of the absolute configuration of sulphostin, a novel inhibitor of dipeptidyl peptidase IV

Journal of Natural Products

Volumn 67, Issue 6, 2004, Pages 999-1004

  Abe, Masatoshi ^a   Akiyama, Tetsuo ^a   Nakamura, Hikaru ^a   Kojima, Fukiko ^a   Harada, Shigeko ^a   Muraoka, Yasuhiko ^a  

^a INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDYL PEPTIDASE IV; DIPEPTIDYL PEPTIDASE IV INHIBITOR; ENZYME INHIBITOR; NATURAL PRODUCT; ORNITHINE; PHOSPHORUS; SULPHOSTIN; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL STRAIN; BACTERIUM CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHIRALITY; CONCENTRATION RESPONSE; CRYSTAL STRUCTURE; CULTURE MEDIUM; DRUG DETERMINATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; ENZYME INHIBITION; EPIMER; IC 50; IN VITRO STUDY; NONHUMAN; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; STEREOCHEMISTRY; STEREOISOMERISM; STREPTOMYCES; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TECHNIQUE; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

ANIMALS; ANTIGENS, CD26; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; INHIBITORY CONCENTRATION 50; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; PIPERIDONES; PROTEASE INHIBITORS; RATS; STEREOISOMERISM; STREPTOMYCES; STRUCTURE-ACTIVITY RELATIONSHIP;

BACTERIA (MICROORGANISMS); STREPTOMYCES; STREPTOMYCES SP.;

EID: 3042531830     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np030491b     Document Type: Article

References (22)

1. Heins, J.; Welker, P.; Schönlein, C.; Born, I.; Hartrodt, B.; Neubert, K.; Tsuru, D.; Barth, A. Biochim. Biophys. Acta 1988, 954, 161-169.
2. Oravecz, T.; Pall, M.; Roderiquez, G.; Gorrell, M. D.; Ditto, M.; Nguyen, N. Y.; Boykins, R.; Unsworth, E.; Norcross, M. A. J. Exp. Med. 1997, 186, 1865-1872.
3. Heymann, E.; Mentlein, R. FEBS Lett. 1978, 91, 360-364.
4. Mentlein, R.; Gallwitz, B.; Schmidt, W. E. Eur. J. Biochem. 1993, 214, 829-835.
5. Pederson, R. A.; White, H. A.; Schlenzig, D.; Pauly, R. P.; McIntosh, C. H. S.; Demuth, H. U. Diadetes 1998, 47, 1253-1258.
6. Balkan, B.; Kwasnik, L.; Miserendino, R.; Holst, J. J.; Li, X. Diabetologia 1999, 42, 1324-1331.
7. Ahrén, B.; Simonsson, E.; Larsson, H.; Landin-Olsson, M.; Torgeirsson, H.; Jansson, P. A.; Sandqvist, M.; Båvenholm, P.; Efendic, S.; Eriksson, J. W.; Dickinson, S.; Holmes, D. Diabetes Care 2002, 25, 869-875.
8. Sorbera, L. A.; Revel, L.; Castañer, J. Drugs Fut. 2001, 26, 859-864.
9. Bristol, L. A.; Sakaguchi, K.; Appella, E.; Doyle, D.; Takács, L. J. Immunol. 1992, 149, 367-372.
10. Vivier, I.; Marguet, D.; Naquet, P.; Bonicel, J.; Black, D.; Li, C. X. Y.; Bernard, A. M.; Gorvel, J. P.; Pierres, M. J. Immunol. 1991, 147, 447-454.
11. Korom, S.; De Meester, I.; Stadlbauer, T. H. W.; Chandraker, A.; Schaub, M.; Sayegh, M. H.; Belyaev, A.; Haemers, A.; Scharpé, S.; Kupiec-Weglinski, J. W. Transplantation 1997, 63, 1495-1500.
12. Tanaka, S.; Murakami, T.; Horikawa, H.; Sugiura, M.; Kawashima, K.; Sugita, T. Int. J. Immunopharmacol. 1997, 19, 15-24.
13. Akiyama, T.; Abe, M.; Harada, S.; Kojima, F.; Sawa, R.; Takahashi, Y.; Naganawa, H.; Homma, Y.; Hamada, M.; Yamaguchi, A.; Aoyagi, T.; Muraoka, Y.; Takeuchi, T. J. Antibiot. 2001, 54, 744-746.
14. Sendai, M.; Hashiguchi, S.; Tomimoto, M.; Kishimoto, S.; Matsuo, T.; Kondo, M.; Ochiai, M. J. Antibiot. 1985, 38, 346-371.
15. Oya, H.; Nagatsu, I.; Nagatsu, T. Biochim. Biophys. Acta 1972, 258, 591-599.
16. Hughes, T. E.; Mone, M. D.; Russell, M. E.; Weldon, S. C.; Villhauer, E. B. Biochemistry 1999, 38, 11597-11603.
17. Coutts, S. J.; Kelly, T. A.; Snow, R. J.; Kennedy, C. A.; Barton, R. W.; Adams, J.; Krolikowski, D. A.; Freeman, D. M.; Campbell, S. J.; Ksiazek, J. F.; Bachovchin, W. W. J. Med. Chem. 1996, 39, 2087-2094.
18. Belyaev, A.; Zhang, X.; Augustyns, K.; Lambeir, A.-M.; De Meester, I.; Vedernikova, I.; Scharpé, S.; Haemers, A. J. Med. Chem. 1999, 42, 1041-1052.
19. 3).
20. 3).
21. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, M.; Giacovazzo, C.; Guagliardi, A.; Polidori, G. J. Appl. Crystallogr. 1994, 27, 435-435.
22. Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).