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SUMMARY:Cysteine Arylation to Engineer Peptides and Proteins
DTSTART:20180626T161500
DTSTAMP:20261002T033656Z
UID:bfc6394a44bc1bf1b63e9c2e196f2767806c92e63e8086ae7947f91a
CATEGORIES:Conferences - Seminars
DESCRIPTION:Bradley L. Pentelute is an Associate Professor with tenure\, a
 t the Department of Chemistry\, Massachusetts Institute of Technology\, (M
 IT) and awardee of the Eli Lilly Award in Biological Chemistry (2018) and 
 BMS Young Investigator Award in Organic Chemistry (2017).\nDuring his talk
 \, Prof. Pentelute will report a robust bioconjugation method using cystei
 ne arylation. This chemistry enables site-specific conjugation at cysteine
  residues within peptides\, proteins\, and antibodies. His two developed a
 pproaches use either perfluoroaryl-cysteine SNAr chemistry or organometal
 lic palladium reagents. This work lead to the discovery of a self-labeling
  four-residue sequence that enables regioselective conjugation at only one
  cysteine residue within an intact antibody containing natural amino acid
 s. Recently\, his lab discovered a new approach for the native conjugatio
 n of complex natural products such as vancomycin onto peptides and protein
 s without the introduction of linkers or chemical handles.\n\nSome relevan
 t publications:\n\n	Cohen\, D.T.\,*  Zhang\, C.\,* Pentelute\, B.L.*\, Bu
 chwald\, S.L.*\, (2015) An Umpolung Approach for the Chemoselective Arylat
 ion of Selenocysteine in Unprotected Peptides\, Journal of the American Ch
 emical Society\, 137(31)\, 9784-7 (*Co-corresponding authors and first aut
 hors)\n	Vinogradova\, E.V.*\, Zhang\, C.*\, Spokoyny\, A. M.\, Pentelute\,
  B.L.*\, Buchwald\, S.L.\,* (2015). Organometallic palladium reagents for 
 cysteine bioconjugation. Nature\, 526(7575)\, 687-691 (*Co-corresponding a
 uthors and first authors)\n	Zhang\, C.\, Welborn\, M.\, Zhu\, T.\, Santos\
 , M.\, Yang\, N.\, Van Voorhis\, T.\, Pentelute\, B.L.\, (2016). π-Clamp 
 mediated cysteine conjugation. Nature Chemistry\, 8(2)\, 120-8\n\n\nProf. 
 Pentelute's research entails the development of cysteine arylation for pro
 duction of antibody drug conjugates\, the use of chemistry to systematical
 ly dissect how anthrax toxin delivers proteins into cells with the goal of
  delivering biomolecular agents (peptides and antibodies mimics) to the cy
 tosol of cells\, and fast flow platforms for the rapid production of chemi
 cally modified biomolecules. Recent work revealed cysteine arylation as a 
 potentially powerful avenue to chemically tailor unprotected peptides and 
 proteins. 
LOCATION:SV 1717 https://plan.epfl.ch/?room==SV%201717
STATUS:CONFIRMED
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