Abstract
In the field of pharmaceuticals and natural product synthesis, enantioselective synthesis is particularly important because different enantiomers of a molecule often display vastly different biological activities. In this project, I aim to devise a synthetic pathway to access enantioenriched thioaminals, 3-Thiaglutamate (1) and its structural analog 3-Thiahomoleucine (2), found in nature. Due to the unstable nature of the products, 3-Thiaamino acids have never been isolated in a pure form. It is suspected that 3-thiaamino acids mimic the function of normal glutamates as a defense signaling molecule in plants. This research will overcome the previous synthetic challenge and prepare the pure products to verify their functions. Also, enantioenriched thioaminals and thioaminoketal functional groups are commonly found in natural product classes such as epithiodiketopiperazines (ETPs). ETPs exhibit biological properties including antiviral, antiproliferative, and antibacterial activities. Expanding on the research of ETP synthesis will facilitate the study of their biological properties to broaden their applications as new antibiotics, and this research will ease the ambiguity in establishing the essential functional groups.
Figure 1. Known structures of Pearlin natural products.