HOST INSTITUTION
Ludwig-Maximilians-Universität München
EMAIL ADDRESS
ilaria.giussani@cup.lmu.de
SUPERVISOR
Prof. Ivan Huc
BRIEF CV
I was born in 2000 in Varese, Italy, where I obtained my high school diploma in 2019. I attended Università degli Studi di Milano where I graduated with a Bachelor’s in Chemistry in 2022 and a Master’s in Chemical Sciences in July 2024. During the Master’s, I studied for the duration of a semester at the Rijksuniversiteit in Groningen, the Netherlands. My master thesis focused on the synthesis of modified fucosides as ligands for the bacterial lectin BC2L-C.
PROJECT DESCRIPTION
Carbohydrates recognition is involved in essential biological events and plays an important role in many pathologies. However, the rational design of synthetic carbohydrate receptors with both high affinity and selectivity remains a challenging task. In professor Huc’s group, synthetic carobohydrate receptors based on folded aromatic oligoamide sequences (or foldamers) have achieved high carbohydrate binding selectivity and affinity: they adopt a stabilized helical conformation in solution, whose shape and size can be modulated to obtain capsule with a cavity suited to accommodate and fully surround the guest. However, the recognition is mainly based on enthalpically favorable polar interactions and is therefore efficient in apolar solvents.
The DC objective is to bring these systems in water, which could pave the way to recognition of carbohydrates in vivo with many possible application.
Recognition in water will rely on the formation of stable cyclic boronate esters between boronic acid moieties and 1,2- or 1,3-diols of the target carbohydrate as a covalent driving force against the cost of desolvating sugars from water. This will ensure high binding affinity and will be combined with the shape selectivity of the foldamers.
A first objective is the synthesis of new aromatic monomers functionalized with the boronic acid moiety and their implementation into sequences. Parallel to the synthesis work, solution binding studies and structural analysis will be performed to give insights into the binding process with boronic acids, and further guide the design.
A second objective will be to make the binding event detectable by e.g. fluorescence so that receptors can serve as sensors.
MAIN RESEARCH FIELD
Organic chemistry, molecular recognition.
