Schreiber's synthesis of this compound had a pipecolinal undergo an Evans-Tischenko fragment coupling, while Ley's version used a Stille coupling to stitch the final product together, and used SnCl4 to cyclize an allyl stannate.
Schreiber's synthesis of this compound had a pipecolinal undergo an Evans-Tischenko fragment coupling, while Ley's version used a Stille coupling to stitch the final product together, and used SnCl4 to cyclize an allyl stannate. The biosynthesis of this molecule, which contains a central macrocycle surrounded by three ketone and two methoxy groups, attaches L-pipecolate to a polyketide, then cyclizes. Originally isolated from S. hygroscopicus, Kennedy and Kaberlein found that administering this compound to rats in mid-life drastically extended lifespan, and it is used instead of calcineurin inhibitors due to the latters' nephrotoxicity. This compound prevents the formation of complex containing G-beta-L, PRAS40, and Raptor, while a related complex containing the Rictor protein is unaffected by it. Marketed as an immune suppressant under the name Sirolimus, it binds to the protein FKBP12, which in turn inhibits a certain kinase. For 10 points, name this antibiotic which notably "Targets" a pathway containing the protein TOR.
Schreiber's synthesis of this compound had a pipecolinal undergo an Evans-Tischenko fragment coupling, while Ley's version used a Stille coupling to stitch the final product together, and used SnCl4 to cyclize an allyl stannate.
{Rapamycin} or {Rapamune} or {Sirolimus} before mention