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Site-specific modification of proteins via aqueous Horner-Wadsworth-Emmons reaction followed by Wolff rearrangement

Grant number: 15/07509-1
Support type:Scholarships abroad - Research Internship - Doctorate
Effective date (Start): October 01, 2015
Effective date (End): September 30, 2016
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Antonio Carlos Bender Burtoloso
Grantee:Barbara Bernardim de Souza
Supervisor abroad: Gonçalo José Lopes Bernardes
Home Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil
Local de pesquisa : University of Cambridge, England  
Associated to the scholarship:12/22274-2 - Study in the photochemical Wolff rearrangement from a,b-unsaturated diazoketones. aplication in diversity synthesis of nitrogen and oxygen heterocycles, BP.DR


This project aims at applying the knowledge on the chemistry of alpha,beta-unsaturated diazoketones, developed in our group, to enable the site-selective modification of proteins in collaboration with Prof. Gonçalo Bernardes at University Of Cambridge, UK. Chemical protein modification has emerged as an invaluable tool for understanding natural systems, create therapeutic conjugates with improved performances, as well as novel protein constructs with desired properties or functions. We intend to address this challenge by employing our recently developed strategy to the synthesis of the nitroxide JP4-039 from ±,²-unsaturated diazoketones to perform chemical modification of proteins (and thus tailor their properties). (AU)

Scientific publications
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
MATOS, MARIA J.; NAVO, CLAUDIO D.; HAKALA, TUULI; FERHATI, XHENTI; GUERREIRO, ANA; HARTMANN, DAVID; BERNARDIM, BARBARA; SAAR, KADI L.; COMPANON, ISMAEL; CORZANA, FRANCISCO; KNOWLES, TUOMAS P. J.; JIMENEZ-OSES, GONZALO; BERNARDES, GONCALO J. L. Quaternization of Vinyl/Alkynyl Pyridine Enables Ultrafast Cysteine-Selective Protein Modification and Charge Modulation. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v. 58, n. 20, p. 6640-6644, MAY 13 2019. Web of Science Citations: 1.
BERNARDIM, BARBARA; MATOS, MARIA J.; FERHATI, XHENTI; COMPANON, ISMAEL; GUERREIRO, ANA; AKKAPEDDI, PADMA; BURTOLOSO, ANTONIO C. B.; JIMENEZ-OSES, GONZALO; CORZANA, FRANCISCO; BERNARDES, GONCALO J. L. Efficient and irreversible antibody-cysteine bioconjugation using carbonylacrylic reagents. Nature Protocols, v. 14, n. 1, p. 86-99, JAN 2019. Web of Science Citations: 2.
BERNARDIM, BARBARA; CAL, PEDRO M. S. D.; MATOS, MARIA J.; OLIVEIRA, BRUNO L.; MARTINEZ-SAEZ, NURIA; ALBUQUERQUE, INES S.; PERKINS, ELIZABETH; CORZANA, FRANCISCO; BURTOLOSO, ANTONIO C. B.; JIMENEZ-OSES, GONZALO; BERNARDES, GONCALO J. L. Stoichiometric and irreversible cysteine-selective protein modification using carbonylacrylic reagents. NATURE COMMUNICATIONS, v. 7, OCT 26 2016. Web of Science Citations: 31.

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