Isolation and Synthetic Diversification of Jadomycin 4-Amino-l-phenylalanine

Abstract

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Investigations into the binding of jadomycin DS to human topoisomerase IIβ by WaterLOGSY NMR spectroscopy

“…12--14 This is accomplished by exploiting a non--enzymatic step within the biosynthetic pathway where an imine is postulated to form through reaction of a biosynthetic aldehyde and an amino acid, followed by cyclization and decarboxylation of the intermediate to yield an oxazolone ring, followed by glycosylation to furnish the jadomycin of interest. 15, 20 Various jadomycin bioactivities have been measured including cytotoxicity profiles in the National Cancer Institute 60--cell line screening, 21 copper--mediated DNA cleavage, 22 photodynamic inactivation of bacteria, 19,23 and aurora B kinase inhibition, 24 indicating that the jadomycins may function as polypharmacologic agents. 11,19 Total synthesis has provided supporting evidence for the non--enzymatic imine formation and cyclization.…”

Harnessing Enzymatic Promiscuity in Myxochelin Biosynthesis for the Production of 5‐Lipoxygenase Inhibitors

“…[19][20][21] Even more noteworthy are the new insights into the structure-activity relationships of the myxochelins. Feeding experiments involving as ingle aromatic substrate usually give access to multiple derivatives, due to randomized incorporation at the two possible positions.…”

“…At otal of 14 new myxochelina naloguesw erei solated and characterized in this study.A ll derivatives were produced in greater amounts than the parental molecule;t his suggests that the cellular pool of 2,3-DHBAi sa limiting factor for myxochelin biosynthesis in P. fallax.F rom a chemicalp erspective, the successful incorporation of 2-fluoroand 2-chlorobenzoic acids has introduced handles that could enable further derivatization of the myxochelin skeleton. [19][20][21] Even more noteworthy are the new insights into the structure-activity relationships of the myxochelins. The catechol residues and,t hus, the presence of iron-complexing bidentate ligand groups turned out to be non-essential for 5-LO inhibition.…”

Characterization of l-Digitoxosyl-phenanthroviridin from Streptomyces venezuelae ISP5230

“…Although production of a jadomycin analogue with the appropriate m/z for L-lysine incorporation was confirmed by LC-MS/MS analysis of the crude growth media, 19 attempts to isolate the product using standard methodologies successfully employed for other jadomycins or by chemical derivatization were unsuccessful due to compound instability. 15,20 During investigations of crude fermentation extracts, we identified an intriguing unknown amber-colored compound by TLC that proved to be sufficiently stable for isolation and characterization. Herein, we report the isolation, characterization, and cytotoxic evaluation of the new phenanthroviridin analogue L-digitoxosyl-phenanthroviridin (1).…”