547762-39-0Relevant articles and documents
Identification of a Pyrrole Intermediate Which Undergoes C-Glycosidation and Autoxidation to Yield the Final Product in Showdomycin Biosynthesis
Kim, Minje,Liu, Hung-wen,Ren, Daan,Wang, Shao-An
supporting information, p. 17148 - 17154 (2021/06/28)
Showdomycin is a C-nucleoside bearing an electrophilic maleimide base. Herein, the biosynthetic pathway of showdomycin is presented. The initial stages of the pathway involve non-ribosomal peptide synthetase (NRPS) mediated assembly of a 2-amino-1H-pyrrole-5-carboxylic acid intermediate. This intermediate is prone to air oxidation whereupon it undergoes oxidative decarboxylation to yield an imine of maleimide, which in turn yields the maleimide upon acidification. It is also shown that this pyrrole intermediate serves as the substrate for the C-glycosidase SdmA in the pathway. After coupling with ribose 5-phosphate, the resulting C-nucleoside undergoes a similar sequence of oxidation, decarboxylation and deamination to afford showdomcyin after exposure to air. These results suggest that showdomycin could be an artifact due to aerobic isolation; however, the autoxidation may also serve to convert an otherwise inert product of the biosynthetic pathway to an electrophilic C-nucleotide thereby endowing showdomycin with its observed bioactivities.
Convenient method for the synthesis of a flexible cyclic polyamide for selective targeting of c-myb G-quadruplex DNA
Zhang, Qiang,Cui, Xiaojie,Lin, Sen,Zhou, Jiang,Yuan, Gu
, p. 6126 - 6129 (2013/02/25)
A convenient efficient method for synthesis of a flexible cyclic polyamide (cβ, 1) was developed through cyclodimerization. Electrospray ionization mass spectrometry and nuclear magnetic resonance results showed that 1 selectively binds to the c-myb G-qua
