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The structure of gephyrotoxin (GTX) 223AB

  • Published:1981-12 Issue:12 Volume:37 Page:1242-1245
  • ISSN:0014-4754
  • Container-title:Experientia
  • language:en
  • Short-container-title:Experientia

Author:

Spande Th. F.,Daly J. W.,Hart D. J.,Tsai Y-M.,Macdonald T. L.

Publisher

Springer Science and Business Media LLC

Subject

Cell Biology,Cellular and Molecular Neuroscience,Pharmacology,Molecular Biology,Molecular Medicine

Reference18 articles.

1. J.W. Daly, G.B. Brown, M. Mensah-Dwumah and C.W. Myers, Toxicon16, 163 (1978). See discussion for GC peak 223AB. The EI spectrum (LKB 3000 spectrometer, 70eV) exhibited a parent ion at m/z 223 (intensity 1% of base peak) and only 2 major fragment ions, one at 180 (loss of C3H7, intensity 66% of base peak) and the other at 166 (loss of C4H9, base peak). This material has been referred to in ref. 14 as GTX-223, since it appeared to be related structurally to gephyrotoxin (GTX)13. Biosynthesis of most dendrobatid alkaloids appears likely to derive from a precursor 2,6-disubstituted piperidine which has odd numbers of carbons in both substituents; cf. histrionicotoxins, pumiliotoxin-C, gephyrotoxin. Because of this, an alternative structure for GTX-223AB, viz. 3-propyl-5-butylindolizidine5, was considered quite unlikely since it would derive from a 2,6-disubstituted piperidine with4 and 6 carbon substituents.

2. J. W. Daly, T. Tokuyama, R. J. Highet and I. L. Karle, J. Am. chem. Soc.102, 830 (1980).

3. J.W. Daly, B. Witkop, T. Tokuyama, T. Nishikawa and I.L. Karle, Helv. chim. Acta60, 1128 (1977).

4. F. J. Ritter, I. E. M. Rotgans, E. Talman, P. E. J. Verwiel and F. Stein, Experientia29, 530 (1973).

5. J. P. Edwards and D. B. Pinninger, Ann. appl. Biol.89, 395 (1978). We have adopted Sonnet's use13 of the E, Z nomenclature to characterize indolizidine stereoisomers. The configuration of the hydrogen atom at C(5) and C(9) is referred to the hydrogen at C(3) and is either in a cis-(Z) or trans-(E) relationship.
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