D'Alonzo Daniele, Cipolletti Manuela, Tarantino Giulia, Ziaco Marcello, Pieretti Giuseppina, Iadonisi Alfonso, Palumbo Giovanni, Alfano Alberto, Giuliano Mariateresa, De Rosa Mario, Schiraldi Chiara, Cammarota Marcella, Parrilli Michelangelo, Bedini Emiliano, Corsaro Maria M
Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, via Cintia 4, 80126, Naples, Italy.
Department of Biology, University "Roma Tre", Viale G. Marconi 446, 00146, Rome, Italy.
Chemistry. 2016 Jul 25;22(31):11053-63. doi: 10.1002/chem.201601284. Epub 2016 Jun 17.
A semisynthetic approach to novel lipid A derivatives from Escherichia coli (E. coli) lipid A is reported. This methodology stands as an alternative to common approaches based exclusively on either total synthesis or extraction from bacterial sources. It relies upon the purification of the lipid A fraction from fed-batch fermentation of E. coli, followed by its structural modification through tailored, site-selective chemical reactions. In particular, modification of the lipid pattern and functionalization of the phosphate group as well as of the sole primary hydroxyl group were accomplished, highlighting the unusual reactivity of the molecule. Preliminary investigations of the immunostimulating activity of the new semisynthetic lipid A derivatives show that some of them stand out as promising, new immunoadjuvant candidates.
