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Synthesis of 3a‐hydroxyhexahydropyrrolo[2,3‐B]Indole‐2‐carboxamide, an oxidation product of tryptophan present in natural products
Author(s) -
Blanc Antoine,
Perrin David M.
Publication year - 2019
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.533
H-Index - 7
ISSN - 2475-8817
DOI - 10.1002/pep2.24082
Subject(s) - indole test , tryptophan , chemistry , dimethyldioxirane , natural product , carboxamide , stereochemistry , organic chemistry , biochemistry , amino acid
The 3 a ‐hydroxyhexahydropyrrolo[2,3‐ b ]indole‐2‐carboxamide (HO‐HPIC) is formed from the oxidation of tryptophan residues and is well represented in peptide‐based natural products. These natural products exhibit potential medicinal activities and thus have caught the attention of chemists and biologists over the past few years. Considerable effort has been marshaled toward the synthesis of HO‐HPIC‐containing natural products, but only a few of these peptides have been successfully synthetically prepared. This review briefly describes a few choice natural products containing the HO‐HPIC motif, summarizes the biological activities and synthetic routes of selected natural compounds containing HO‐HPIC, and emphasizes the use of dimethyldioxirane (DMDO) in the oxidation of tryptophan and its derivatives to HO‐HPIC‐containing motifs.