Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

Allopumiliotoxin 267A

From Wikipedia, the free encyclopedia
Allopumiliotoxin 267A
Names
Preferred IUPAC name
(6E,7R,8R,8aS)-8-Methyl-6-[(2R)-2-methylhexylidene]octahydroindolizine-7,8-diol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C16H29NO2/c1-4-5-7-12(2)10-13-11-17-9-6-8-14(17)16(3,19)15(13)18/h10,12,14-15,18-19H,4-9,11H2,1-3H3/b13-10+/t12-,14+,15-,16-/m1/s1 checkY
    Key: LWXKAVPXEDNHLL-VRUXTKGDSA-N checkY
  • InChI=1/C16H29NO2/c1-4-5-7-12(2)10-13-11-17-9-6-8-14(17)16(3,19)15(13)18/h10,12,14-15,18-19H,4-9,11H2,1-3H3/b13-10+/t12-,14+,15-,16-/m1/s1
    Key: LWXKAVPXEDNHLL-VRUXTKGDBX
  • O[C@@H]1C(=C\[C@H](C)CCCC)\CN2[C@H]([C@]1(O)C)CCC2
Properties
C16H29NO2
Molar mass267.413 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly toxic
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Allopumiliotoxin 267A is a toxin found in the skin of severalpoison frogs of the familyDendrobates.[1] It is a member of the class of compounds known asallopumiliotoxins. The frogs produce the toxin by modifying the original version,pumiliotoxin 251D.[2] It has been tested on mice and found to be five times more potent than the former version. It has been produced synthetically through a variety of different routes.[3][4][5][6]

See also

[edit]

References

[edit]
  1. ^Edwards, M. W.; Daly, J. W.; Myers, C. W. (1988). "Alkaloids from a Panamanian poison frog, Dendrobates speciosus: Identification of pumiliotoxin-A and allopumiliotoxin class alkaloids, 3,5-disubstituted indolizidines, 5-substituted 8-methylindolizidines, and a 2-methyl-6-nonyl-4-hydroxypiperidine".Journal of Natural Products.51 (6):1188–97.doi:10.1021/np50060a023.PMID 3236011.
  2. ^Daly, J. W.; Garraffo, H. M.; Spande, T. F.; Clark, V. C.; Ma, J.; Ziffer, H.; Cover Jr, J. F. (2003)."Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates".Proceedings of the National Academy of Sciences of the United States of America.100 (19):11092–7.Bibcode:2003PNAS..10011092D.doi:10.1073/pnas.1834430100.PMC 196932.PMID 12960405.
  3. ^Comins, D. L.; Huang, S.; McArdle, C. L.; Ingalls, C. L. (2001). "Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: A concise asymmetric synthesis of (+)-allopumiliotoxin 267A".Organic Letters.3 (3):469–71.doi:10.1021/ol0069709.PMID 11428041.
  4. ^Franklin, Alison S.; Overman, Larry E. (1996). "Total Syntheses of Pumiliotoxin a and Allopumiliotoxin Alkaloids. Interplay of Pharmacologically Active Natural Products and New Synthetic Methods and Strategies".Chemical Reviews.96 (1):505–522.doi:10.1021/cr950021p.PMID 11848762.
  5. ^Tang, Xiao-Qing; Montgomery, John (2000)."Nickel-Catalyzed Preparation of Bicyclic Heterocycles: Total Synthesis of (+)-Allopumiliotoxin 267A, (+)-Allopumiliotoxin 339A, and (+)-Allopumiliotoxin 339B".Journal of the American Chemical Society.122 (29):6950–6954.Bibcode:2000JAChS.122.6950T.doi:10.1021/ja001440t.
  6. ^Aoyagi, Sakae; Wang, Tzu Chueh; Kibayashi, Chihiro (1993). "Highly stereoselective total syntheses of (+)-allopumiliotoxins 267A and 339A via intramolecular nickel(II)/Chromium(II)-mediated cyclization".Journal of the American Chemical Society.115 (24):11393–11409.Bibcode:1993JAChS.11511393A.doi:10.1021/ja00077a044.
Bacterial
toxins
Exotoxin
Gram
positive
Bacilli
Clostridium:
Other:
Cocci
Staphylococcus
Actinomycetota
Gram
negative
Mechanisms
Endotoxin
Virulence
factor
Mycotoxins
Plant toxins
Invertebrate
toxins
Scorpion:
Spider:
Mollusca:
Vertebrate
toxins
Fish:
Amphibian:
Reptile/
Snake venom:
  • note: some toxins are produced by lower species and pass through intermediate species
Retrieved from "https://en.wikipedia.org/w/index.php?title=Allopumiliotoxin_267A&oldid=1264681906"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2025 Movatter.jp