Biosynthesis of the azoxycarboxamide lyophyllin and formation of some of its unnatural analogues in fruit-bodies of Lyophyllum connatum

Tetrahedron Letters

Volumn 38, Issue 46, 1997, Pages 8013-8016

  Ye, Yang ^a   Aulinger, Katharina ^a   Arnold, Norbert ^a   Spahl, Werner ^a   Steglich, Wolfgang ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AZOXY DERIVATIVE; HYDROXAMIC ACID DERIVATIVE; LYOPHYLLIN; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; DRUG STRUCTURE; MUSHROOM; REACTION ANALYSIS;

EID: 0030784859     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10177-0     Document Type: Article

References (23)

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6. a) Elaiomycin : Stevens, C.L.; Gillis, T.B.; French, J.C. and Haskell, T.H. J. Am. Chem. Soc. 1956, 78, 3229-3230. LL-BH872α : McGahren, W.J. and Kunstmann, M.P. J. Am. Chem. Soc. 1972, 37, 902-906; Valanimycin : Yamato, M.; Iinuma, H.; Naganawa, H.; Yamagishi, Y.; Hamada, M.; Masuda, T. and Umezawa, H. J. Antibiot. 1986, 39, 184-191. Jietacin A : Omura, S.; Otoguru, K.; Imamura, N.; Kuga, H.; Takahashi, Y.; Masuma, R.; Tanaka, Y.; Tanaka, H.; Su, X. and You, E. J. Antibiot. 1987, 40, 623-629; Imamura, N.; Kuga, H.; Otoguru, K.; Tanaka, H. and Omura, S. J. Antibiot. 1989, 42, 156-158; Maniwamycins : Nakayama, M.; Takahashi, Y.; Itoh, H.; Kamiya, K.; Shiratsuchi, M. and Otani, G. J. Antibiot. 1989, 42, 1535-1540; Nakayama, M.; Watanabe, I.; Deushi, T.; Ishiwata, H.; Shiratsuchi, M. and Otani, G. J. Antibiot. 1989, 42, 1541-1546.
7. a) Elaiomycin : Stevens, C.L.; Gillis, T.B.; French, J.C. and Haskell, T.H. J. Am. Chem. Soc. 1956, 78, 3229-3230. LL-BH872α : McGahren, W.J. and Kunstmann, M.P. J. Am. Chem. Soc. 1972, 37, 902-906; Valanimycin : Yamato, M.; Iinuma, H.; Naganawa, H.; Yamagishi, Y.; Hamada, M.; Masuda, T. and Umezawa, H. J. Antibiot. 1986, 39, 184-191. Jietacin A : Omura, S.; Otoguru, K.; Imamura, N.; Kuga, H.; Takahashi, Y.; Masuma, R.; Tanaka, Y.; Tanaka, H.; Su, X. and You, E. J. Antibiot. 1987, 40, 623-629; Imamura, N.; Kuga, H.; Otoguru, K.; Tanaka, H. and Omura, S. J. Antibiot. 1989, 42, 156-158; Maniwamycins : Nakayama, M.; Takahashi, Y.; Itoh, H.; Kamiya, K.; Shiratsuchi, M. and Otani, G. J. Antibiot. 1989, 42, 1535-1540; Nakayama, M.; Watanabe, I.; Deushi, T.; Ishiwata, H.; Shiratsuchi, M. and Otani, G. J. Antibiot. 1989, 42, 1541-1546.
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20. GC/MS was carried out on a Varian Model 3400 GC coupled to a Finnigan MAT 95Q sector mass spectrometer using EI at 70 eV. The helium flow was 1 ml/min, the injector and coupling temp. 250°C. 1 μl solution was injected with a split of 1:10. Fused-silica capillary columns were used: J&W DB-1701 (15 m × 0.25 mm id). Column temp. programming: maintained at 50°C for 2 min, then heating to 300°C (10°C/min), then maintained at 300°C for 3 min.
21. +], 140 (7), 98 (100, A), 70 (41, B), 56 (51), 55 (92). The stereochemistry of lyophyllin (3) and its analogues 5 is unknown.
22. A similar range of 'unnatural' precursors was accepted by fruit-bodies of Hebeloma sacchariolens in their conversion of anthranilic acid to 2-aminobenzaldehyde: v. Nussbaum, F.; Spahl, W. and Steglich, W. Phytochemistry 1997, 46, 261-264.
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