| Summary: | Being a methyl ester of partricin, the mepartricin complex is the active substance of a drug called Ipertrofan (Tricandil), which was proven to be useful in treatment of benign prostatic hyperplasia and chronic nonbacterial prostatitis/chronic pelvic pain syndrome. Nevertheless, no direct structural evidence on the stereochemistry of its components has been presented to date. In this contribution, we have conducted detailed, NMR-driven stereochemical studies on mepartricins A and B, aided by molecular dynamics simulations. The absolute configuration of all the stereogenic centers of mepartricin A and B was defined as 3<i>R</i>, 7<i>R</i>, 9<i>R</i>, 11<i>S</i>, 13<i>S</i>, 15<i>R</i>, 17<i>S</i>, 18<i>R</i>, 19<i>S</i>, 21<i>R</i>, 36<i>S</i>, 37<i>R</i>, and 38<i>S</i>, and proposed as 41<i>R</i>. The geometry of the heptaenic chromophore of both compounds has been established as 22<i>E</i>, 24<i>E</i>, 26<i>E</i>, 28<i>Z</i>, 30<i>Z</i>, 32<i>E</i>, and 34<i>E</i>. Our studies on mepartricin ultimately proved that partricins A and B are structurally identical to the previously described main components of the aureofacin complex: gedamycin and vacidin, respectively. The knowledge of the stereochemistry of this drug is a fundamental matter not only in terms of studies on its molecular mode of action, but also for potential derivatization, aiming at improvement of its pharmacological properties.
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