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Plakohypaphorine

From Wikipedia, the free encyclopedia

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.
This page was last edited on 17 September 2023, at 17:48
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