Surf Wiki
Save to docs
general/alpha-amino-acids

From Surf Wiki (app.surf) — the open knowledge base

Plakohypaphorine

Plakohypaphorines are halogenated indolic non-proteinogenic amino acids named for their similarity to hypaphorine (N,N,N-trimethyltryptophan). First reported in the Caribbean sponge Plakortis simplex in 2003, plakohypaphorines A-C were the first iodine-containing indole alkaloids to be discovered in nature. Plakohypaphorines D-F, also found in P. simplex, were reported in 2004 by a group including the researchers who discovered the original plakohypaphorines.

PlakohypaphorineChemical nameChemical formulaSMILESImage
Plakohypaphorine7-Iodo-*N,N,N*-trimethyltryptophanC14H17IN2O2OC(=O)C(N(C)(C)C)Cc2cnc1c2cccc1I[[Image:Plakohypaphorine A.svg200pxclass=skin-invert-imageChemical structure of Plakohypaphorine A]]
Plakohypaphorine B6,7-Diiodo-*N,N,N*-trimethyltryptophanC14H16I2N2O2OC(=O)C(N(C)(C)C)Cc2cnc1c2ccc(I)c1I[[Image:Plakohypaphorine B.svg200pxclass=skin-invert-imageChemical structure of Plakohypaphorine B]]
Plakohypaphorine C5,7-Diiodo-*N,N,N*-trimethyltryptophanC14H16I2N2O2CN(C)(C)C(C(=O)O)Cc2cnc1c2cc(I)cc1I[[Image:Plakohypaphorine C.svg200pxclass=skin-invert-imageChemical structure of Plakohypaphorine C]]
Plakohypaphorine D5,6-Diiodo-*N,N,N*-trimethyltryptophanC14H16I2N2O2Ic2cc1c(cc2I)ncc1CC(C(O)=O)N(C)(C)C[[Image:Plakohypaphorine D.svg200pxclass=skin-invert-imageChemical structure of Plakohypaphorine D]]
Plakohypaphorine E5,6,7-Triiodo-*N,N,N*-trimethyltryptophanC14H15I3N2O2CN(C)(C)C(C(=O)O)Cc1cnc(c(I)c2I)c1cc2I[[Image:Plakohypaphorine E.svg200pxclass=skin-invert-imageChemical structure of Plakohypaphorine E]]
Plakohypaphorine F6-Chloro-5-iodo-*N,N,N*-trimethyltryptophanC14H16ClIN2O2Clc2c1ncc(CC(C(O)=O)N(C)(C)C)c1cc(I)c2[[Image:Plakohypaphorine F.svg200pxclass=skin-invert-imageChemical structure of Plakohypaphorine F]]

References

  • Taglialatela-Scafati Orazio et al., 2003. Plakohypaphorines A-C, Iodine-Containing Alkaloids from the Caribbean Sponge Plakortis simplex. European Journal of Organic Chemistry. 2003(2), pp. 284–287.
  • Borrelli, Francesca, et al., 2004. Iodinated Indole Alkaloids From Plakortis simplex, New Plakohypaphorines and an Evaluation of Their Antihistamine Activity. European Journal of Organic Chemistry. 2004(15), pp. 3227–3232.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

alpha-amino-acids halogen-containing-alkaloids 5-halotryptamines non-proteinogenic-amino-acids organoiodides n,n,n-trialkyltryptamines tryptamine-alkaloids zwitterions
Want to explore this topic further?

Ask Mako anything about Plakohypaphorine — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report