Testero Sebastian A, O'Daniel Peter I, Shi Qicun, Lee Mijoon, Hesek Dusan, Ishiwata Akihiro, Noll Bruce C, Mobashery Shahriar
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Org Lett. 2009 Jun 18;11(12):2515-8. doi: 10.1021/ol900668k.
The unique hydrophobic surface patches in class D beta-lactamases presented an opportunity for designing two compounds, 6alpha-(1R-hydroxyoctyl)penicillanic acid and 6beta-(1R-hydroxyoctyl)penicillanic acid, as mechanistic probes of these enzymes. In a sequence of three synthetic steps from benzhydryl 6,6-dibromopenicillanate, the targeted compounds were prepared in a stereospecific manner.
D类β-内酰胺酶中独特的疏水表面区域为设计两种化合物提供了契机，即6α-(1R-羟基辛基)青霉烷酸和6β-(1R-羟基辛基)青霉烷酸，作为这些酶的作用机制探针。以二苯甲基6,6-二溴青霉酸酯为原料，经过三步合成反应，以立体特异性方式制备了目标化合物。
