Aureolic acid group

Aureolic acid group of antibiotics We have given below an extended summary of the work done with this group of antibiotics, because we have been actively involved in understanding the mode of action of these DNA-binding antibiotics. The summary also illustrates the model example of how different biophysical and biochemical approaches were undertaken to characterize the association of these drugs with chromosomal DNA and the sequential effect of this binding upon the chromatin structure. 

J. Rohr, C. Mendez, and J. A. Salas, The biosynthesis of aureolic acid group antibiotic, Bioorg. Chem., 27 (1998) 41-54. 

Aureolic acids are a group of tetrahydroanthracene oligosaccharide antibiotics, the name of which is related to their characteristic golden appearance. Members of the aureolic acid group include chromomycin A3, olivomycin A and mithramycin, as the most prominent examples (O Fig. 15). 

Members of the aureolic acid group include chromomycin A3 (42), olivomycin A (43) and mithramycin (plicamycin) (44). The aglycon of chromomycin A3 is identical to that of mithramycin, but differs from that of olivomycin A by a methyl group. Conversely, the sugar components for chromomycin A3 and olivomycin are nearly identical, while those in mithramycin are different (O Scheme 17). 

Aureolic acid group antibiotics cyclopentanoid antibiotics prostaglandins. 

Aureolic acid group antibiotics, Y16 Aureomycin, Y28 Austamide, KS ... 

Members of this group feature tricyclic carbon framework decorated with two oligosaccharide chains. Mithramycin 48 and chromomycin A3 49 are two aureolic acids that have found their use in cancer chemotherapy. These compounds, interacting with Mg2+, bind GC-rich DNA in a nonintercalative way, and sugar chains are indispensable in stabilizing metal-antibiotic complexes. Carbohydrates are... 

D-Olucose has been converted to the aureolic acid fragment 57, while D-mannitol has been converted to the la,25-dihydroxyvitamin D3 ring A synthon 59 via cyanohydrin 58. The abstract reported no synthetic details, but the cyclization is likely to proceed by displacement of the tosyloxy group by an a-cyano carbanion. 

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