Frederick G West

Significance Biological membranes are typically built from lipids bearing one polar headgroup and two hydrophobic tails, but synthetic chemistry allows for alternative architectures. Here, we show that single-chain bolalipids with proline headgroups self-assemble into stable vesicles while exhibiting distinct interfacial behavior relative to a unipolar analog.

1 Introduction Breast cancer is the most frequently diagnosed cancer among women, accounting for 25% of all new cancer diagnoses and 14% of cancer-related deaths worldwide.[1] While advances in early detection and treatment have improved 5-year survival rates to 78–90%, metastatic breast cancer, particularly the triple-negative subtype, remains incurable.[2] It is associated with earlier recurrence and poorer survival outcomes, particularly in stage IV disease.

Formation and rearrangement of several oxonium ylides containing cyclopropylcarbinyl migrating groups were studied. Efficient ring-contraction by [1,2]-shift to form cyclopropane-substituted cyclobutanones was observed, with no competing cyclopropane fragmentation.