58147-58-3Relevant academic research and scientific papers
Improved synthesis of the super antioxidant, ergothioneine, and its biosynthetic pathway intermediates
Khonde, Peguy Lutete,Jardine, Anwar
, p. 1415 - 1419 (2015)
Ergothioneine and mycothiol are low molecular mass redox protective thiols present in actinomycetes, in particular mycobacteria. We report the improved chemical synthesis of ergothioneine (ESH) and biosynthetic pathway intermediates using either histidine or ESH as the starting material. The detailed mechanism of ESH biosynthesis has not yet been completely elucidated and substrates for enzymes in the pathway will provide valuable tools to aid this study. Particularly interesting is the PLP dependent β-lyase, EgtE, of mycobacteria, having the capability of cleaving the substrate, S-(β-amino-β-carboxyethyl)ergothioneine sulfoxide, to provide ESH. A synthetic route toward ESH pathway intermediates also allowed the preparation of stable isotopically labelled hercynine-d3 which was enzymatically transformed into ESH-d3. The deuterated ergothioneine biosynthetic pathway metabolites are valuable tools for future studies.
Synthesis of Highly Substituted 3-Pyrrolin-2-ones from N,N-Disubstituted α-Amino Acids
Samper Barceló, Víctor,Bienz, Stefan
, p. 2734 - 2743 (2018/03/09)
Highly functionalized 5-membered N-heterocyclic compounds, 4-aryl-3-chloro-5-methoxy-1-methyl-3-pyrrolin-2-ones, have been synthesized in moderate to high yields by the reaction of N,N-dimethylated aromatic α-amino acids with oxalyl chloride, followed by solvolysis with MeOH. The products possess a number of functional groups such as an amide, a mixed amido/alkoxy acetal, a vinyl halide, and an alkene and thus are promising candidates to be used as starting materials for the synthesis of diverse five-membered N-heterocyclic compounds.
Pelianthinarubins A and B, Red Pyrroloquinoline Alkaloids from the Fruiting Bodies of the Mushroom Mycena pelianthina
Pulte, Anna,Wagner, Silke,Kogler, Herbert,Spiteller, Peter
, p. 873 - 878 (2016/05/24)
Pelianthinarubin A (1) and pelianthinarubin B (2), two previously unknown pyrroloquinoline alkaloids, have been isolated from fruiting bodies of Mycena pelianthina. The structures of these alkaloids have been deduced from their HR-(+)-ESIMS and 2D NMR data. The absolute configurations of the pelianthinarubins A (1) and B (2) were assigned by analysis of the NOE correlations and coupling constants and by comparison of the CD spectra of 1 and 2 and of hercynine obtained by degradation of 1 with suitable compounds of known absolute configuration. The pelianthinarubins A (1) and B (2), which contain an S-hercynine moiety, differ considerably from the known pyrroloquinoline alkaloids from marine organisms and other Mycena species, such as the mycenarubins, the haematopodins, and the sanguinones.
