|Synthesis and Derivatization of Complex Natural Products|
: 195 : 2015.03.30 10:15
|일시 : 2015.04.01 17:00|
|소속 : KAIST, Department of Chemistry|
|발표자 : 한순규|
|장소 : R404|
Part 1. Total synthesis of all (-)-trigonoliimines
Enantioselective total synthesis of all known trigonoliimines will be presented. Synthetic routes consist of an asymmetric oxidation and rearrangements of 2,3-disubstituted tryptamine derivative. Common hydroxyindolenine intermediates were diverted to trigonoliimines with different molecular structures under attentively chosen reaction conditions, transformations with possible biosynthetic relevance.
Part 2. Site-selective phosphorylation of teicoplanin
Development of three peptide-based catalysts for the site-selective phosphorylation of three distinct sugar units in teicoplanin derivative will be discussed. Two of the catalysts exploit the high affinity between the DXaa-DXaa and teicoplanin, the interaction that plays a crucial role in the mode of action of glycopeptide antibiotics. Mechanistic studies based on the x-ray crystal structure of the catalyst-bound teicoplanin, which was obtained through a carrier protein strategy will also be presented.