| Organic Chemistry
To develop new synthetic methodologies based on fluorous synthesis, multicomponent reactions, free radical reactions, and asymmetric organocatalysis.
To develop new synthetic and separation processes with good atom economy, energy efficiency, product separation and chemical recycling capability, and minimal waste disposal.
To design and synthesize drug-like molecules and natural product analogs for biological screenings at our collabrator's labs
To develop new fluorous technologies and their applications in organic, separation, biological, and material sciences.
Our group is a leader in the application of fluorous techniques for solution-phase parallel and combinatorial synthesis of chemical libraries.
Students in this group will learn advanced synthetic and analytical skills related to HPLC, LC-MS, NMR, microwave reactor, solid-phase extraction, and chiral separations.
- Prof. Stephen J. Elledge, Harvard Medical School, Department of Genetics, New affinity reagent for purification of specific targets from a library of human proteins displayed on ribosomes (Nat. Biotechnol. 2013, 31, 331).
- Profs. Nathanael S. Gray and Priscilla Yang, Harvard Medical School & Dana-Farber Cancer Institute. Small molecule probes of cancer cell lines and virus infection (ChemBioChem 2014, 15, 1317; BioSystems 2012, 8, 2523).
- Profs. James Bradner and Jun Qi, Harvard Medical School & Dana-Farber Cancer Institute. New inhibitors for bromodomains (ChemMedChem 2016, 11, 2575; J. Med. Chem. 2014, 57, 9019).
- Profs. Steve P. Treon and Sara Buhrlage, Harvard Medical School & Dana-Farber Cancer Institute. HCK Is a Survival Determinant Transactivated by Mutated MYD88, and A Direct Target of Ibrutinib (Blood, 2016, 127, 3237-3252).
- Profs. Dan Littman, NYU Medical School, and Jun Huh, UMass Medical School. New inhibitors for RORgt.
- Prof. Jian Zhu, University of Rochester Medical School, New inhibitors to revert latent HIV.
- Profs. Hong Zhang and Rachel M. Gerstein, UMass Medical School. BET bromodomain inhibitors for large B-cell lymphoma.
- Prof. William C. Pomerantz, University of Minnesota. Fluorescently-labeled small molecules as bromodomain and kinase inhibitors (ACS Chem. Biol. 2015, 10, 2246).
- Profs. Kenichiro Todoroki and Toshimasa Toyo'oka, University of Shizuoka (Japan), Fluorous chiral stationary phases for LC (Analytica Chimica Acta 2015, 882, 101).
- Prof. Helio A. Stefani, Universidade de Sao Paulo (Brazil), Green organic and medicinal chemistry.
- Drs. Michael Kopach (Eli Lilly), Fabrice Gallou (Novartis), Paul Richardson and Zhao-Kui Wan (Pfizer), Green solvents for Grignard reactions (Green Chem. 2013, 15, 1880).
- Dr. Berkeley W. Cue, green chemistry and medicinal chemistry (Green Techniques for Organic Synthesis and Medicinal Chemistry, Zhang, W. and Cue, B. W. Eds., Wiley, Chichester, 2012).
- Prof. Vadim A. Soloshonok, University of the Basque Country UPV/EHU (Spain), Self-disproportionation of enantiomers.
- Profs. Dennis P. Curran and Peter Wipf, University of Pittsburgh, Center for Chemical Methodologies and Library Development (CMLD). Synthesis of drug-like heterocyclic compound libraries (Chem. Commun. 2010, 46, 7578; J. Comb. Chem. 2009, 11, 452; J. Org. Chem. 2009, 74, 5481; Tetrahedron 2006, 62, 11837; Eur. J. Org. Chem. 2006, 2055; J. Am. Chem. Soc. 2002, 124, 10443).
- Fluorous Technologies, Inc. New fluorous synthetic technologies and library synthesis (Chem. Commun. 2010, 46, 7578; J. Comb. Chem. 2010, 12, 125; J. Org. Chem, 2009, 74, 5481).
- Profs. Chun Cai and Wenbin Yi, Nanjing University of Science & Technology (China). Fluorous synthesis, organofluorination and green chemistry (Adv. Synth. Catal. 2016, 358, 2811; J. Org. Chem. 2016, 81, 5362; Org. Lett. 2016, 18, 5640; Adv. Synth. Catal. 2015, 357, 3820; Angew. Chem. Int. Ed. 2015, 54, 14965; Org. Lett. 2015, 17, 1090; J. Fluorine Chem. 2014, 157, 84; RSC Advances 2013, 3, 18267; Green Chem. 2012, 14, 3185; Chem. Commun. 2008, 5686).
- Prof. Jian-Ping Zou, Suzhou University (China). Free radical reactions and heterocyclic compound synthesis (Green Chem. 2017, 19, 919; Tetrahedron 2015, 71, 7481; J. Org. Chem. 2014, 79, 1850; Synthesis 2013, 45, 152; Chem. Commun. 2011, 47, 7875; Green Chem. 2011, 594; Chem. Commun. 2010, 46, 1721; Org. Lett. 2006, 8, 52911).
- Prof. Chung-Ming Sun, National Chiao-Tung University (Taiwan). Fluorous synthesis of chemical libraries (ACS Comb. Sci. 2013, 15, 350; J. Comb. Chem. 2007, 9, 951).
- Prof. Gang Liu, Chinese Academy of Medical Sciences & Peking Union Medical College (China). Fluorous glycopeptide chemistry (J. Org. Chem. 2009, 74, 2594).
- Prof. Bing Yan, St. Jude Children's Research Hospital. Fluorous synthesis of heterocyclic compound libraries (J. Comb. Chem. 2008, 10, 303; J. Comb. Chem. 2009, 11, 1083; J. Comb. Chem. 2010, 12, 206).
- Prof. Koichi Mikami, Tokyo Institute of Technology (Japan). Fluorous racemic mixture synthesis (Chirality 2008, 20, 597).
- Dr. John Williams, Neurocrine, San Diego, CA. Fluorous synthesis of natural product analogs (Tetrahedron Lett. 2007, 48, 563).
- Dr. Daniel Kassel, Takeda-San Diego, CA. MS-trigged parallel F-HPLC analysis and purification techniques (J. Comb. Chem. 2006, 8, 687).
- Dr. Paul Tempest, Amgen. San Francisco, CA. Microwave-assisted fluorous multicomponent reactions (Tetrahedron Lett. 2004, 45, 6757)
- Prof. Michael A. Parniak, University of Pittsburgh, School of Medicine. Mappicine Inhibitors of HIV-1 Reverse Transcriptase - Associated Ribonuclease H.
- 2017 - 2018, Conference grant for 7th Int. Symposium of Fluorous Technologies, UMass Boston Office of Global Program Seed Grant, Principal Investigator.
- 2016 - 2017, Collaboration on Green Chemistry with Shanghai Institute of Technology (SIT), UMass Boston Office of Global Program Seed Grant, Principal Investigator.
- 2016 - 2019, Cooperation of TAT-interacting Proteins to Regulate HIV Latenc, NIH R33AI116180-03, Co-Investigator (PI J. Zhu).
- 2016, The Development of New Bromodomain Inhibitors for Cancer and Other Diseases, UMass Boston PhD Thesis Grant (Shuai Liu), PhD Sponsor.
- 2016, Green Organocatalysts for the Synthesis of Fluorinated Compounds with Biological Interest, UMass Boston PhD Thesis Grant (Xin Huang), PhD Sponsor.
- 2015 - 2020, Investigation of Latency Promoting Genes (LPGs) in HIV Oral Reservoir Cells, NIH R01DE025447, Co-Investigator (PI J. Zhu).
- 2014 - 2016, Diversity Supplement Grant, NIH/NCI U54CA156734, Postdoc Sponsor.
- 2014 - 2015, Green Organocatalysis for Asymmetric Synthesis of Biologically Interesting Fluorinated Compounds, UMass Boston Healey Grant, Principal Investigator.
- 2014 - 2015, Lead Optimization of Inhibitors for Nuclear Receptor RORgt, sponsored by Medical School, New York, University.
- 2013 - 2015, Development of Small-Molecule Bromodomain Inhibitors for Cancer Therapy, NIH U54CA156734, Co-PI of a full project.
- 2012 - 2013, Synthesis and Screening of Chemical Libraries for Discovery of Novel Bromodomain Inhibitors, NIH U54CA156734, Co-PI of a pilot project.
- 2012 - 2014, Green chemistry and medicinal chemistry collaboration of University of Massachusetts Boston and Universidade de Sao Paulo.Santander - Top USA Massachusetts Program, Co-PI.
- 2011 - 2012, Grignard Reaction Research, ACS Green Chemistry Institute Pharmaceutical Roundtable, Principal Investigator.
- 2011 - 2012, Postdoc Training Program, sponsored by Enablence, Postdoc sponsor.
- 2011 - 2012, Development of Recyclable Fluorous Bifunctional Organocatalysts, Proposal Development Grant Program, UMass Boston, Principal Investigator.
- 2011 - 2012, Synthesis of Compounds for Screening Against Nuclear Receptor RORgt, sponsored by Medical School, New York, University.
- 2010 - 2013, Covalent Fluorescent Probes for Cancer Cell Detection, NIH U54CA156734, Co-PI of a full project.
- 2010 - 2013, Selective Extraction into Fluorous Media, NSF0957038, Co-Investigator (PI Steve Weber)
- 2010 - 2011, International Symposium on Green Chemistry, NIH R13GM096683, Principal Investigator.
- 2010, Mentoring Program for Undergraduate Research on Green Chemistry, UMass Boston CSM Program for Instructional Innovation, Principal Investigator.
- 2009 - 2010, Development of New Green Techniques for Medicinal Chemistry Applications, JHG FY10-H10-26, UMass Boston Healey Grant, Principal Investigator.
- 2009 - 2010, Development of Fluorescent Small Molecule Probes of Cancer Cell Lines, NIH U56CA118635, Co-PI of a pilot project
- 2007 - 2010, Diversity-Oriented Synthesis of Novel Heterocyclic and Natural Product-Like Libraries, NIH P41GM081269, Principal Investigator.
- 2007 - 2009, Fluorous Solution-Phase Synthesis of Peptides and Oligosaccharides, NIH Phase II STTR, R41GM075436, Co-Investigator.
- 2005 - 2010, Mitochondrial Targeting Against Radiation Damage, NIH U19AI068021, Principal Investigator of Core C.
- 2004 - 2007, Rapid Fluorous Synthesis of Drug-Like Small Molecules NIH Phase II SBIR, R44GM067326, Principal Investigator.
- 2003 - 2005, Mappicine Inhibitors of HIV Ribonuclease H, NIH Phase I STTR, R41AI0541098-01, Co-Investigator.
- 2003 - 2004, Mappicine RNase H Inhibitors, 2003 HIV Drug Discovery and Development Research Grant, GlaxoSmithKline, PrincipalInvestigator.
- 2002 - 2004, Solution Phase Libraries by Fluorous Mixture Synthesis, NIH-Phase II SBIR R44GM062717, Principal Investigator.
- 2001 - 2002, Mappicine Libraries by Fluorous Mixture Synthesis, NIH-Phase I SBIR, R43GM62717, Principal Investigator.