%0 Journal Article %1 kudo2021identification %A Kudo, Yuta %A Hanifin, Charles T. %A Yotsu-Yamashita, Mari %D 2021 %J Organic Letters %K biosynthesis newts tetrodotoxin %N 9 %P 3513-3517 %R 10.1021/acs.orglett.1c00916 %T Identification of Tricyclic Guanidino Compounds from the Tetrodotoxin-Bearing Newt Taricha granulosa %U https://doi.org/10.1021/acs.orglett.1c00916 %V 23 %X The biosynthesis of the potent neurotoxin tetrodotoxin (TTX, 1) is still unresolved. We used MS-guided screening and nuclear magnetic resonance analyses including long-range HSQMBC to characterize two novel skeletal tricyclic guanidino compounds, Tgr-288 (2a and 2b) and Tgr-210 (3), from the TTX-bearing newt, Taricha granulosa. The presence of these compounds in toxic newts is congruent with a previously proposed pathway for TTX biosynthesis in terrestrial organisms that includes a monoterpene precursor and the production of structurally diversified guanidino compounds.

@article{kudo2021identification, abstract = { The biosynthesis of the potent neurotoxin tetrodotoxin (TTX, 1) is still unresolved. We used MS-guided screening and nuclear magnetic resonance analyses including long-range HSQMBC to characterize two novel skeletal tricyclic guanidino compounds, Tgr-288 (2a and 2b) and Tgr-210 (3), from the TTX-bearing newt, Taricha granulosa. The presence of these compounds in toxic newts is congruent with a previously proposed pathway for TTX biosynthesis in terrestrial organisms that includes a monoterpene precursor and the production of structurally diversified guanidino compounds. }, added-at = {2024-07-05T06:14:44.000+0200}, author = {Kudo, Yuta and Hanifin, Charles T. and Yotsu-Yamashita, Mari}, biburl = {https://www.bibsonomy.org/bibtex/2b190538710163ee4e9813b01e32aa45a/peter.ralph}, doi = {10.1021/acs.orglett.1c00916}, eprint = {https://doi.org/10.1021/acs.orglett.1c00916}, interhash = {54bf08faa1764146411c2cf8a944d39e}, intrahash = {b190538710163ee4e9813b01e32aa45a}, journal = {Organic Letters}, keywords = {biosynthesis newts tetrodotoxin}, number = 9, pages = {3513-3517}, timestamp = {2024-07-05T06:14:44.000+0200}, title = {Identification of Tricyclic Guanidino Compounds from the Tetrodotoxin-Bearing Newt \textit{{Taricha} granulosa}}, url = {https://doi.org/10.1021/acs.orglett.1c00916 }, volume = 23, year = 2021 }