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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 indoles 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.

Plakohypaphorine Chemical name Chemical formula SMILES Image
Plakohypaphorine 7-Iodo-N,N,N-trimethyltryptophan C14H17IN2O2 OC(=O)C(N(C)(C)C)Cc2cnc1c2cccc1I Chemical structure of Plakohypaphorine A
Plakohypaphorine B 6,7-Diiodo-N,N,N-trimethyltryptophan C14H16I2N2O2 OC(=O)C(N(C)(C)C)Cc2cnc1c2ccc(I)c1I Chemical structure of Plakohypaphorine B
Plakohypaphorine C 5,7-Diiodo-N,N,N-trimethyltryptophan C14H16I2N2O2 CN(C)(C)C(C(=O)O)Cc2cnc1c2cc(I)cc1I Chemical structure of Plakohypaphorine C
Plakohypaphorine D 5,6-Diiodo-N,N,N-trimethyltryptophan C14H16I2N2O2 Ic2cc1c(cc2I)ncc1CC(C(O)=O)N(C)(C)C Chemical structure of Plakohypaphorine D
Plakohypaphorine E 5,6,7-Triiodo-N,N,N-trimethyltryptophan C14H15I3N2O2 CN(C)(C)C(C(=O)O)Cc1cnc(c(I)c2I)c1cc2I Chemical structure of Plakohypaphorine E
Plakohypaphorine F 6-Chloro-5-iodo-N,N,N-trimethyltryptophan C14H16ClIN2O2 Clc2c1ncc(CC(C(O)=O)N(C)(C)C)c1cc(I)c2 Chemical 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.