Syntheses of antifungal aureobasidin A analogs with alkyl chains for structure-activity relationship

Journal of Antibiotics

Volumn 51, Issue 3, 1998, Pages 359-367

  Kurome, Toru ^a   Inoue, Tetsuya ^a   Takesako, Kazutoh ^a   Kato, Ikunoshin ^a   Inami, Kaoru ^b   Shiba, Tetsuo ^b  

^a TAKARA SHUZO CO LTD   (Japan)

^b Protein Research Foundation   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKYL GROUP; ANTIFUNGAL AGENT; AUREOBASIDIN DERIVATIVE; CARBOXYL GROUP; GLUTAMIC ACID; NORVALINE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA; CANDIDA GLABRATA; CONTROLLED STUDY; CRYPTOCOCCUS NEOFORMANS; DRUG SYNTHESIS; ESTERIFICATION; LIPOPHILICITY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; SACCHAROMYCES CEREVISIAE; STRUCTURE ACTIVITY RELATION;

EID: 0031923118     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.51.359     Document Type: Article

References (14)

1. TAKESAKO, K.; K. IKAI, F. HARUNA, M. ENDO, K. SHIMANAKA, E. SONO, T. NAKAMURA, I. KATO & H. YAMAGUCHI: Aureobasidins, new antifungal antibiotics. J. Antibiotics 44: 919-924, 1991
2. TAKESAKO, K.; H. KURODA, T. INOUE, F. HARUNA, Y. YOSHIKAWA, I. KATO, K. UCHIDA, T. HIRATANI & H. YAMAGUCHI: Biological properties of aureobasidin A, a cyclic depsipeptide antifungal antibiotic. J. Antibiotics 46: 1414-1420, 1993
3. IKAI, K.; K. TAKESAKO, K. SHIOMI, M. MORIGUCHI, Y. UMEDA, J. YAMAMOTO & I. KATO: Structure of aureobasidin A. J. Antibiotics 44: 925-933, 1991
4. IKAI, K.; K. SHIOMI, K. TAKESAKO & I. KATO: NMR studies of aureobasidin A and E. J. Antibiotics 44: 1199-1207, 1991
5. BENZ, F.; F. KNUSEL, J. NUESCH, H. TREICHLER, W. VOSER, R. NYFELER & W. KELLER-SCHIERLEIN: Stoffwechselprodukte von Mikroorganismen. Echinocandin B, ein Neuartiges Polypeptid-antibioticum aus Aspergillus nidulans var. echinulatus: Isolierung und Bausteine. Helv. Chim. Acta 57: 2459-2477, 1974
6. DEBONO, M.; B. J. ABBOTT, D. S. FUKUDA, M. BARNHART, K. E. WILLARD, R. M. MOLLOY, K. H. MICHEL, J. R. TURNER, T. F. BUTLER & A. H. HUNT: Synthesis of new analogs of echinocandin B by enzymatic deacylation and chemical reaction of the echinocandin B peptide: Synthesis of the antifungal agent cilofungin (LY 121019). J. Antibiotics 42: 389-397, 1989
7. IKAI, K.; K. SHIOMI, K. TAKESAKO, S. MIZUTANI, J. YAMAMOTO, Y. OGAWA, M. UENO & I. KATO: Structures of aureobasidins B to R. J. Antibiotics 44: 1187-1198, 1991
8. YOSHIKAWA, Y.; K. IKAI, Y. UMEDA, A. OGAWA, K. TAKESAKO & I. KATO: Isolation, structures, and antifungal activities of new aureobasidins. J. Antibiotics 46: 1347-1354, 1993
9. AWAZU, N.; K. IKAI, J. YAMAMOTO, K. NISHIMURA, S. MIZUTANI, K. TAKESAKO & I. KATO: Structures and antifungal activities of new aureobasidins. J. Antibiotics 48: 525-527, 1995
10. KUROME, T.; K. INAMI, T. INOUE, K. IKAI, K. TAKESAKO, I. KATO & T. SHIBA: Total synthesis of an antifungal cyclic depsipeptide aureobasidin A. Tetrahedron 52: 4327-4346, 1996
11. TAKESAKO, K.; S. MIZUTANI, H. SAKAKIBARA, M. ENDO, Y. YOSHIKAWA, T. MASUDA, E. SONO-KOYAMA & I. KATO: Precursor directed biosynthesis of aureobasidins. J. Antibiotics 49: 676-681, 1996
12. 4. Chem. Lett. 1979: 981-982, 1979
13. CHEUNG, S. T. & N. LEO BENOITON: N-Methylamino acids in peptide synthesis. V. The synthesis of N-tert-butyloxy-carbonyl, N-methylamino acids by N-methylation. Can. J. Chem. 55: 906, 1977
14. INAMI, K.; T. KUROME, K. TAKESAKO, I. KATO & T. SHIBA: Site-specific ring opening of depsipeptide aureobasidin A in hydrogen fluoride. Tetrahedron Lett. 37: 2043-2044, 1996