Synthesis of 3a‐hydroxyhexahydropyrrolo[2, 3‐B]Indole‐2‐carboxamide, an oxidation product of tryptophan present in natural products. Issue 1 (14th November 2018)

• Record Type: Journal Article
• Authors: Blanc, Antoine; Perrin, David M.
• Other Names: Lubell William D. guestEditor.
• Is Part Of: Peptide science. Volume 111:Issue 1(2019)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2018-11-14
• Subjects: indoline -- peptide natural product -- tryptophan oxidation; Peptides -- Periodicals; 572.6505
• DOI: 10.1002/pep2.24082
• Languages: English
• ISSNs: 2475-8817

Abstract

Abstract: 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. Abstract :