2,5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products.

Bioactive peptides: A review

Recent advances in asymmetric organocatalysis mediated by bifunctional amine–thioureas bearing multiple hydrogen-bonding donors

Sirodesmin PL is a phytotoxin produced by the fungus Leptosphaeria maculans, which causes blackleg disease of canola (Brassica napus). This phytotoxin belongs to the epipolythiodioxopiperazine (ETP) class of toxins produced by fungi including mammalian and plant pathogens. We report the cloning of a cluster of genes with predicted roles in the biosynthesis of sirodesmin PL and show via gene disruption that one of these genes (encoding a two-module non-ribosomal peptide synthetase) is essential for sirodesmin PL biosynthesis. Of the nine genes in the cluster tested, all are co-regulated with the production of sirodesmin PL in culture. A similar cluster is present in the genome of the opportunistic human pathogen Aspergillus fumigatus and is most likely responsible for the production of gliotoxin, which is also an ETP. Homologues of the genes in the cluster were also identified in expressed sequence tags of the ETP producing fungus Chaetomium globosum. Two other fungi with publicly available genome sequences, Magnaporthe grisea and Fusarium graminearum, had similar gene clusters. A comparative analysis of all four clusters is presented. This is the first report of the genes responsible for the biosynthesis of an ETP.

https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1365-2958.2004.04215.x

The sirodesmin biosynthetic gene cluster of the plant pathogenic fungus Leptosphaeria maculans.

Diketopiperazines (DKPs), which are cyclic dipeptides, have been detected in a variety of natural resources Recently, the interest in these compounds increased significantly because of their remarkable bioactivity This review deals with the chemical structures, biosynthetic pathways, and biological activities of DKPs from marine microorganisms, sponges, sea stars, tunicates (ascidians), and red algae The literature has been covered up to December 2008, and a total 124 DKPs from 104 publications have been discussed and reviewed Some of these compounds have been found to possess various bioactivities including cytotoxicity, and antibacterial, antifungal, antifouling, plant-growth regulatory, and other activities

Diketopiperazines from marine organisms.

New dioxopiperazine metabolites from a Fusarium species separated from a marine alga.

New Dioxopiperazine Metabolites from a Fusarium Species Separated from a Marine Alga.

Marine Natural Products. Part 37. Aragusteroketals A and C, Two Novel Cytotoxic Steroids from a Marine Sponge of Xestospongia sp.

Marine Natural Products. Part 38. Absolute Stereostructures of Altohyrtins A, B, and C and 5-Desacetylaltohyrtin A, Potent Cytotoxic Macrolides, from the Okinawan Marine Sponge Hyrtios altum.

Palladium(II)-Catalyzed Oxidation of Carbon-Carbon Double Bonds of Allylic Compounds with Molecular Oxygen. Regioselective Formation of Aldehydes.

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