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Xanthopsin-like systems via site-specific click-functionalization of a retinoic acid binding protein

DOI: 10.1002/cbic.202100449 DOI Help

Authors: Giusy Tassone (University of Siena) , Marco Paolino (University of Siena) , Cecilia Pozzi (University of Siena) , Annalisa Reale (University of Siena) , Laura Salvini (Toscana Life Sciences Foundation) , Gianluca Giorgi (University of Siena) , Maurizio Orlandini (University of Siena) , Federico Galvagni (University of Siena) , Stefano Mangani (University of Siena) , Xuchun Yang (Bowling Green State University) , Benedetta Carlotti (University of Perugia) , Fausto Ortica (University of Perugia) , Loredana Latterini (University of Perugia) , Massimo Olivucci (University of Siena) , Andrea Cappelli (University of Siena)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Chembiochem

State: Published (Approved)
Published: October 2021
Diamond Proposal Number(s): 15832 , 21741

Abstract: The use of light-responsive proteins to control both living or synthetic cells, is at the core of the expanding fields of optogenetics and synthetic biology. It is thus apparent that a richer reaction toolbox for the preparation of such systems is of fundamental importance. Here, we provide a proof-of-principle demonstration that Morita-Baylis-Hillman adducts can be employed to perform a facile site-specific, irreversible and diastereoselective click-functionalization of a lysine residue buried into a lipophilic binding pocket and yielding an unnatural chromophore with an extended π-system. In doing so we effectively open the path to the in vitro preparation of a library of synthetic proteins structurally reminiscent of xanthopsin eubacterial photoreceptors. We argue that such library, made of variable unnatural chromophores inserted in an easy to mutate and crystallize retinoic acid transporter, significantly expand the scope of the recently introduced rhodopsin mimics as both optogenetic and "lab-on-a-molecule" tools.

Journal Keywords: Morita-Baylis-Hillman adducts; synthetic Xanthopsin-like proteins; site-specific reaction; light-sensitive proteins; PYP-like chromophores

Subject Areas: Biology and Bio-materials, Chemistry

Instruments: I03-Macromolecular Crystallography , I04-Macromolecular Crystallography

Added On: 18/10/2021 09:59

Discipline Tags:

Organic Chemistry Life Sciences & Biotech Structural biology Chemistry Biochemistry

Technical Tags:

Diffraction Macromolecular Crystallography (MX)