Determination of absolute configuration and biological activity of new immunosuppressants, mycestericins D, E, F and G

Journal of Antibiotics

Volumn 49, Issue 9, 1996, Pages 846-853

  Fujita, Tetsuro ^d   Hamamichi, Norimitsu ^a   Kiuchi, Masatoshi ^c   Matsuzaki, Tohru ^a   Kitao, Yuki ^e   Inoue, Kenichiro ^b   Hirose, Ryoji ^b   Yoneta, Masahiko ^b   Sasaki, Shigeo ^b   Chiba, Kenji ^c  

^a KYOTO UNIVERSITY   (Japan)

^b Research Laboratory   (Japan)

^c Yoshitomi Pharmaceutical Industries Ltd   (Japan)

^d SETSUNAN UNIVERSITY   (Japan)

^e GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IMMUNOSUPPRESSIVE AGENT; MYCESTERICIN; THERMOZYMOCIDIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG ISOLATION; DRUG POTENCY; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; FERMENTATION; LYMPHOCYTE PROLIFERATION; MIXED LYMPHOCYTE REACTION; NONHUMAN; PRIORITY JOURNAL; RAT; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION;

EID: 10244265918     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.49.846     Document Type: Article

References (12)

1. 2+ of peptaibols using electrospray ionization mass spectrometry. J. Mass Spectrometry 31: 177-183, 1966
2. FUJITA, T.; K. INOUE, S. YAMAMOTO, T. IKUMOTO, S. SASAKI, R. TOYAMA, K. CHIBA, Y. HOSHINO & T. OKUMOTO: Fungal metabolites. Part 11. A potent immunosuppressive activity found in Isaria sinclairii metabolite. J. Antibiotics 47: 208-215, 1994
3. KLUEPFEL, D.; J. BAGLI, H. BAKER, M.-P. CHAREST, A. KUDELSKI, S. N. SEGAL & C. VEZINA: Myriocin, a new antifungal antibiotic from Myriococcum albomyces. J. Antibiotics 25: 109-115, 1972
4. BAGLI, J. F.; D. KLUEPFEL & M. ST-JACQUES: Elucidation of structure and stereochemistry of myriocin. A novel antifungal antibiotic. J. Org. Chem. 38: 1253-1260, 1973
5. ARAGOZZINI, F.; P. L. MANACHINI, R. CRAVERI, B. RINDONE & C. SCOLASTICO: Isolation and structure determination of a new antifungal α-hydroxymethyl-α-amino acid. Tetrahedron 28: 5493-5498, 1972
6. SASAKI, S.; R. HASHIMOTO, M. KIUCHI, K. INOUE, T. IKUMOTO, R. HIROSE, K. CHIBA, Y. HOSHINO, T. OKUMOTO & T. FUJITA: Fungal metabolite. Part 14. Novel potent immunosuppressants, mycestericins, produced by Mycelia sterilia. J. Antibiotics 47: 420-433, 1994
7. FUJITA, T.; N. HAMAMICHI, T. MATSUZAKI, Y. KITAO, M. KIUCHI, M. NODE & R. HIROSE: Determination of the absolute configurations and total synthesis of new immunosuppressants, mycestericins E and G. Tetrahedron Lett. 36: 8599-8602, 1995
8. SEEBACH, D. & J. D. AEBI: α-Alkylation of serine with self-reproduction of the center of chirality. Tetrahedron Lett. 25: 2545-2548, 1984
9. SINGH, N.P.; A. GIANNIS, E. HENK, T. KOLTER, K. SANDHOFF & R. R. SCHMIDT: Synthesis of 2-carboxy-substituted sphingosine derivatives. J. Carbohydrate Chemistry. 9: 543-559, 1990
10. KUSUMI, T.; Y. FUJITA, I. OHTANI & H. KAKISAWA: Anomaly in the modified Mosher's method: absolute configurations of some marine cembranolides. Tetrahedron Lett. 32: 2923-2926, 1991
11. FUJITA, T.; M. YONETA, R. HIROSE, S. SASAKI, K. INOUE, M. KIUCHI, S. HIRASE, K. ADACHI, M. ARITA & K. CHIBA: Simple compounds, 2-alkyl-2-amino-1,3-propanediols have potent immunosuppressive activity. BioMed. Chem. Lett. 5: 847-852, 1995
12. ADACHI, K.; T. KOHARA, N. NAKAO, M. ARITA, K. CHIBA, T. MISHINA, S. SASAKI & T. FUJITA: Design, synthesis, and structure-activity relationships of 2-substituted-2-amino-1,3-propanediols: discovery of a novel immunosuppressant, FTY720. BioMed. Chem. Lett. 5: 853-856, 1995