One aspect of the invention relates to hexafluoroleucine and congeners thereof, and methods of making the compounds. Another aspect of the invention relates to the synthesis of protein cores comprising hexafluoroleucine and congeners thereof. Certain peptides comprising hexafluoroleucine and congeners thereof have been characterized using comparative biophysical studies. In general, the fluorinated peptides show higher thermal stability and enhanced resistance to chemical denaturation. Further, mixed hydrocarbon-fluorocarbon cores self-sort into homogeneous bundles, suggesting new avenues for the design and manipulation of protein-protein interfaces.
Non-Racemic Hexafluoreleucine, And Methods Of Making And Using It
Alfio Fichera - Malden MA, US Zihni Bilgicer - Somerville MA, US Krishna Kumar - Cambridge MA, US Xuechao Xing - Wilmington MA, US
International Classification:
C07C327/30 C07C237/20
US Classification:
558/256000, 560/156000, 562/553000, 564/163000
Abstract:
One aspect of the invention relates to hexafluoroleucine and congeners thereof, and methods of making the compounds. Another aspect of the nvention relates to the synthesis of protein cores comprising hexafluoroleucine and congeners thereof. Certain peptides comprising hexafluorleucine and congeners thereof have been characterized using comparative biophysical studies. In general, the fluorinated peptides show higher thermal stability and enhanced resistance to chemical denaturation. Further, mixed hydrocarbonfluorocarbon cores self-sort into homogeneous bundles, suggesting new avenues for the design and manipulation of protein-protein interfaces.
Pfizer
Technical Writer and Scientist
Concert Pharmaceuticals, Inc. Jul 2014 - Mar 2015
Scientist
Eisai Oct 2012 - Dec 2013
Medicinal and Process Chemist
Cubist Pharmaceuticals Oct 2011 - Aug 2012
Process Development Scientist
Beta Pharma, Inc. May 2010 - Nov 2011
Senior Scientist
Education:
Massachusetts Institute of Technology Sep 2009
Tufts University 2004
Tufts University 1998 - 2004
Doctorates, Doctor of Philosophy, Chemistry, Organic Chemistry
Graduate School of Arts and Sciences 2001
Master of Science, Masters
Tufts University 2001
Master of Science, Masters, Organic Chemistry
Graduate School of Arts and Sciences 1999
College of the Holy Cross 1990 - 1994
Bachelors, Bachelor of Arts, Chemistry
Central Catholic High School
Graduate School of Arts and Sciences
Doctorates, Doctor of Philosophy
Skills:
Organic Synthesis Hplc Drug Discovery Organic Chemistry Bioconjugate Chemistry Mass Spectrometry Crystallization Peptide Synthesis Pharmaceutical Process Development Radiochemistry Dna Damage
Eisai Inc Andover, MA Oct 2012 to Dec 2013 Scientist (contract), Oncology PCUCubist Pharmaceuticals Lexington, MA Oct 2011 to Aug 2012 Process Development Scientist (contract)BetaPharma, Inc Branford, CT Apr 2010 to Oct 2011 Senior ScientistMassachusetts Institute of Technology
Sep 2004 to Sep 2009 Postdoctoral Associate/Senior Postdoctoral AssociateTufts University
Jan 1999 to Sep 2004 Graduate Student in the laboratory of Prof. Krishna KumarCubist Pharmaceuticals Cambridge, MA Mar 1997 to Jan 1999 Research AssociateMass. Dept. of Environmental Protection Lawrence, MA Sep 1994 to Dec 1996 Intern
Education:
Tufts University 2004 Ph.D. in ChemistryTufts University 2001 M.S. in ChemistryCollege of the Holy Cross 1994 B.A. in Chemistry
Eisai Inc Andover, MA Oct 2012 to Dec 2013 Scientist (contract), Oncology PCUCubist Pharmaceuticals Lexington, MA Oct 2011 to Aug 2012 Process Development Scientist (contract)BetaPharma, Inc Branford, CT Apr 2010 to Oct 2011 Senior ScientistMassachusetts Institute of Technology Cambridge, MA Sep 2004 to Sep 2009 Senior Postdoctoral AssociateTufts University
Jan 1999 to Sep 2004 Graduate Student in the laboratory of Prof. Krishna KumarCubist Pharmaceuticals Cambridge, MA Mar 1997 to Jan 1999 Research AssociateMass. Dept. of Environmental Protection Lawrence, MA Sep 1994 to Dec 1996 Intern
Education:
Tufts University 2004 Ph.D. in ChemistryTufts University 2001 M.S. in ChemistryCollege of the Holy Cross 1994 B.A. in Chemistry