Allopumiliotoxin 267A is a toxin found in the skin of several poison frogs of the family Dendrobates.[1] It is a member of the class of compounds known as allopumiliotoxins. 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]
^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.
^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. PMC196932. PMID 12960405.
^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.
^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.
^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. doi:10.1021/ja001440t.
^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. doi:10.1021/ja00077a044.
April 11, 2024
allopumiliotoxin, 267a, toxin, found, skin, several, poison, frogs, family, dendrobates, member, class, compounds, known, allopumiliotoxins, frogs, produce, toxin, modifying, original, version, pumiliotoxin, 251d, been, tested, mice, found, five, times, more, . Allopumiliotoxin 267A is a toxin found in the skin of several poison frogs of the family Dendrobates 1 It is a member of the class of compounds known as allopumiliotoxins 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 Allopumiliotoxin 267A NamesPreferred IUPAC name 6E 7R 8R 8aS 8 Methyl 6 2R 2 methylhexylidene octahydroindolizine 7 8 diolIdentifiersCAS Number 73376 38 2 Y3D model JSmol Interactive imageChemSpider 4580699 YPubChem CID 5470308UNII TEP57TLJ38 YInChI 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 YKey LWXKAVPXEDNHLL VRUXTKGDSA N YInChI 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 s1Key LWXKAVPXEDNHLL VRUXTKGDBXSMILES O C H 1C C C H C CCCC CN2 C H C 1 O C CCC2PropertiesChemical formula C 16H 29N O 2Molar mass 267 413 g mol 1HazardsOccupational safety and health OHS OSH Main hazards Highly toxicExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesSee also editPumiliotoxin AllopumiliotoxinReferences edit 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 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 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 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 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 doi 10 1021 ja001440t 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 doi 10 1021 ja00077a044 Retrieved from https en wikipedia org w index php title Allopumiliotoxin 267A amp oldid 1182211472, wikipedia, wiki, book, books, library,
