Website | Home URL |
Division | Organic |
Title |
|
Specialties |
|
harran@chem.ucla.edu | |
Office | Molecular Sciences Building 5505A |
Office Phone | (310) 825-6463 |
Lab | Molecular Sciences Building 5210 |
Office Lab | (310) 825-1512 |
Biography
Professor Harran was raised in the Adirondacks region of Upstate New York and trained in chemistry at Skidmore College. He spent three years working with Raymond Giguere on the use of sequenced bimolecular ene / intramolecular Diels-Alder reactions. He carried out doctoral studies with Frederick Ziegler at Yale University. There they explored behavior of photochemically-generated radical intermediates in the synthesis of optically active pyrroloindoles related to mitomycins. He then moved to Stanford University as an NIH sponsored postdoctoral fellow, working with Paul Wender to create simplified, functional analogs of bryostatin. In late 1997 Professor Harran accepted his first independent appointment in the Biochemistry Department at the University of Texas Southwestern Medical Center. He was promoted to Associate Professor with tenure in 2002 and Full Professor in 2005. During his time at Southwestern, the institution built a nationally recognized program in organic chemistry. In the summer of 2008 Professor Harran accepted the inaugural D.J. & J.M. Cram Chair in Organic Chemistry at UCLA.
Research Interests
We study architectural aspects of building molecules. This is expressed through exercises in total synthesis, the development of reactions and processes, and in attempts to generally emulate small-molecule biosynthetic schemes. We seek to create new structures in new ways, and for those molecules to have valuable biological functions.
Honors & Awards
- Inaugural Robert Foster Cherry Lecture on Research and Education, 2019
- JSPS Fellow and International Organic Chemistry Foundation Yoshida Lectureship, 2017
- Herbert Newby McCoy Award, 2016
- Hanson-Dow Award for Excellence in Teaching, 2013
- Glenn T. Seaborg Award – Alpha Chi Sigma, 2009
- Norman Hackerman Prize of the Robert A. Welch Foundation, 2007
- E. Bright Wilson Prize – Harvard University, 2005
- Merck Research Laboratories Chemistry Council Award, 2005-2007
- Mar Nell and F. Andrew Bell Distinguished Chair, 2005
- Pfizer Award for Creativity in Organic Synthesis, 2003
- Distinguished Alumni Award, Skidmore College, 2003
- Eli Lilly Grantee, 2003-2004
- AstraZeneca Excellence in Chemistry Award, 2002
- Alfred P. Sloan Research Fellow, 2002-2004
- National Science Foundation CAREER Award, 2000-2004
- National Research Service Award, Stanford University, 1995-1997
- Bristol-Myers Squibb Research Fellow, Yale University, 1993
- American Institute of Chemists Award, Skidmore College, 1990
- Highest Departmental Honors in Chemistry, Skidmore College, 1990
- One Year Advanced Admission, Skidmore College, 1986
Representative Publications
- Gabriella I. D. Cooper, Ishika Saha, Jacob Newman, Ruthy H. Shin, and Patrick G. Harran (2024). Indolizinylalanine Regioisomers: Tryptophan Isosteres with Bathochromic Fluorescence Emission J. Org. Chem., (Featured on the Cover of a Special Issue on Next-Generation Organic Chemistry for Labeling and Imaging), DOI: 10.1021/acs.joc.4c01203
- Haowen Tian, William Lee, Yuli Li, Morris J. Dweck, Angel Mendoza, Patrick G. Harran, K. N. Houk (2024). Origin of Octafluorocyclopentene Polyelectrophilicity J. Am. Chem. Soc., DOI: 10.1021/jacs.3c12690
- Angel Mendoza, Salvador J. Bernardino, Morris J. Dweck, Isabel Valencia, Declan Evans, Haowen Tian, William Lee, Yu Li, Kendall N. Houk, and Patrick G. Harran (2023). Cascade Synthesis of Fluorinated Spiroheterocyclic Scaffolding for Peptidic Macrobicycles J. Am. Chem. Soc., DOI: 10.1021/jacs.3c03071
- Patrick G. Harran, Salvador Bernadino, Angel Mendoza and Morris Dweck (2023). Methods of Synthesizing Fluorinated Macrocycles U.S. Provisional Patent Application No. 63/489,603, Filed Mar.10, 2023
- Patrick G. Harran, Paul M. Seidler, Darsheed Mustafa, Melinda Balbirnie, Anton El Khoury, Kevin A. Murray and David S. Eisenberg (2022). Agents and Methods for Treating Tauopathies U.S. Patent App. Ser No. 17/927,639, Filed Nov.23, 2022
- Aleksandras Lotuzas, Anton El Khoury, Liubo Li and Patrick G. Harran (2022). Synthesis and Reactivity of a Stable Prototropic Isomer of 2-Acetyl-3-methyl-pyrrole Synlett, (special issue in honor of Masahiro Murakami) DOI: 10.1055/a-1969-4095
- Liubo Li, Anton El Khoury, Brennan O’Neil Clement, Carolyn Wu and Patrick G. Harran (2022). Asymmetric Organocatalysis Enables Rapid Assembly of Portimine Precursor Chains Org. Lett., DOI: 10.1021/acs.orglett.2c00556
- Emily S. Murzinski, Ishika Saha, Hui Ding, David Strugatsky, Ryan A. Hollibaugh, Haixia Liu, Peter Tontonoz and Patrick G. Harran (2021). In Search of Small Molecules That Selectively Inhibit MBOAT4 Molecules, (special issue in honor of Professor Daniel Comin’s) DOI: 10.3390/molecules26247599
- Ishika Saha and Patrick G. Harran (2021). Virtual Screening for Chemists ACS In Focus, DOI: 10.1021/acsinfocus.7e5001
- Anton El Khoury, Paul M. Seidler, David S. Eisenberg and Patrick G. Harran (2021). Catalytic synthesis of PEGylated EGCG conjugates that disaggregate Alzheimer’s tau Synthesis, (special issue in honor of Professor Sarah Reisman) DOI: 10.1055/a-1509-5904
- Liubo Li, Anton El Khoury, Brennan O. Clement and Patrick G. Harran (2021). Re-visiting the diastereoselectivity of organocatalytic conjugate addition of 2-trimethylsiloxyfuran to trans-crotonaldehyde Tetrahedron Lett., (special issue in honor of Professor Dale Boger) 72: 153056
- Evan E. Hurlow, Janice B. Lin, Morris J. Dweck, Selbi Nuryyeva, Zhengao Feng, Tyler K. Allred, K. N. Houk, and Patrick G. Harran (2020). Photorearrangement of [8]-2,6-Pyridinophane N-Oxide. J. Am. Chem. Soc., 142(49): 20717–20724
- Sarah Fogarty, Yeyun Ouyang, Liubo Li, Yu-Chan Chen, Hallie Rane, Francesco Manoni, Karlett J. Parra, Jared Rutter, and Patrick G. Harran (2020). Callyspongiolide Is a Potent Inhibitor of the Vacuolar ATPase. J. Nat. Prod., 83(11): 3381–3386
- Ishika Saha, Eric K. Dang, Dennis Svatunek, Kendall N. Houk, and Patrick G. Harran (2020). Computational generation of an annotated gigalibrary of synthesizable, composite peptidic macrocycles. Proc. Natl. Acad. Sci. (USA) 117: 24679–24690.
- Luke J. Sisto and Patrick G. Harran (2020). Syntheses of Hybrid Cyclopeptidyl [n]sulfanes by Internal Alkyl Group Exchange. Tet. Lett., 61(24): 151985.
- Luke J. Sisto and Patrick G. Harran (2020). Sulfane Transalkylations and Metal Catalyzed Allylic Substitutions for the Synthesis of Composite Macrobicyclic Peptides. Tet. Lett., 61(24): 151986.
- Patrick G. Harran and Emily Murzinski (2020). Compositions And Methods For Treating Obesity. Provisional Patent Application 62/979,915. Filed Feb. 21, 2020
- Tomoyuki Tsunemi, Salvador J. Bernardino, Angel Mendoza, Christopher G. Jones and Patrick G. Harran (2020). Syntheses of atypically fluorinated peptidyl macrocycles via sequential vinylic substitutions, Angew. Chem. Intl. Ed., 59(2): 674-678.
- Zhengao Feng, Tyler K. Allred, Evan E. Hurlow and Patrick G. Harran (2019). Anomalous Chromophore Disruption Enables an Eight-Step Synthesis and Stereochemical Reassignment of (+)-Marineosin A, J. Am. Chem. Soc., 141(6): 2274-2278.
- Hui Ding, Andrew Roberts, Rocky Chiang and Patrick G. Harran (2018). Cascading auto-oxidative biproline guanylations form optically active dispacamide dimers and permit an eight-step synthesis of (−)-ageliferin, J. Org. Chem. (Special Issue on the Synthesis of Antibiotics and Related Molecules), 83(13): 7231-7238.
- Brice Curtin, Francesco Manoni, Jiyong Park, Luke Sisto, Yu-hong Lam, Michel Gravel, Anne Roulston and Patrick G. Harran (2018). Assembly of Complex Macrocycles by Incrementally Analgamating Unprotected Peptides with a Designed Four-Armed Insert, J. Org. Chem., 83(6): 3090-3108.
- Francesco Manoni, Corentin Rumo, Liubo Li, and Patrick G. Harran (2018). Unconventional fragment usage enables a concise total synthesis of (-)-callyspongiolide. J. Am. Chem. Soc., 140(4): 1280-1284.
- Patrick G. Harran, Peter Tontonoz, David Strugatsky, Hui Ding, and Emily Murzinski (2017). Inhibitors of Ghrelin O-Acyl Transferase. Provisional Patent Application. Filed Dec. 20, 2017
- Tyler K. Allred, Francesco Manoni and Patrick G. Harran (2017). Exploring the Boundaries of ‘Practical’: De Novo Synthesis of Complex Natural Product-Based Drug Candidates. Chemical Reviews, 117(18): 11994-12051.
- Michal Wieczorek, Joseph Tcherkezian, Cynthia Bernier, Andrea E. Prota, Sami Chaaban, Yannève Rolland, Claude Godbout, Mark A. Hancock, Joseph C. Arezzo, Ozhan Ocal, Cecilia Rocha, Natacha Olieric, Anita Hall, Hui Ding, Alexandre Bramoullé, Matthew G. Annis, George Zogopoulos, Patrick G. Harran, Thomas M. Wilkie, Rolf. A. Brekken, Peter M. Siegel, Michel O. Steinmetz, Gordon C. Shore, Gary Brouhard and Anne Roulston (2016). The synthetic diazonamide DZ-2384 has distinct effects on microtubule curvature and dynamics without neurotoxicity. Sci. Transl. Med., 8, 365ra159.*For a highlight of this article, see Nature Reviews Drugs Discovery.
- Tristin E. Rose, Brice H. Curtin, Kenneth V. Lawson, Adam Simon, K. Houk and Patrick G. Harran (2016). On the prevalence of bridged macrocyclic pyrroloindolines formed in regiodivergent alkylations of tryptophan. Chem. Sci., 7, 4158-4166.
- Hui Ding, Patrick L. DeRoy, Christian Perreault, Alexandre Larivée, Arshad Siddiqui, Charles G. Caldwell, Susan Harran and Patrick G. Harran (2015). Electrolytic Macrocyclizations: Scalable Synthesis of a Diazonamide-Based Drug Development Candidate. Angew. Chem Intl. Ed. Engl., 54, 4818-4822.
- Jack D. Bracken, Andrew D. Carlson, James H. Frederich, Mai Nguyen, Gordon C. Shore and Patrick G. Harran (2015). Tailored fragments of roseophilin selectively antagonize Mcl-1 in vitro. Tetrahedron Lett. (Special issue in honor of Harry Wasserman), 56, 3612-3616.
- Tristan E. Rose, Kenneth V. Lawson and Patrick G. Harran (2015). Large Ring-Forming Alkylations Provide Facile Access to Composite Macrocycles. Chem. Sci., 6, 2219-2223.
- Patrick G. Harran, Ryan A. Hollibaugh, Haixia Liu (2014). Small Lipopeptidomimetic Inhibitors of Ghrelin O-Acyl Transferase. US Provisional Patent Application #62/051,701. Filed September 17, 2014.
- Patrick G. Harran, James H. Frederich, Gordon Shore and Mai Nguyen (2014). MCL-1 Antagonists. US Provisional Patent Application #61/947,211. Filed March 3, 2014.
- Kenneth V. Lawson, Tristan E. Rose, Patrick G. Harran (2013). Template Constrained Macrocyclic Peptides Prepared from Native, Unprotected Precursors. Proc. Natl. Acad. Sci. (USA), 110 (40), E3753-E3760.
- Kenneth V. Lawson, Tristan E. Rose, Patrick G. Harran (2013). Template-induced macrocycle diversity through large-ring forming alkylations of tryptophan. Tetrahedron (Special issue in honor of P.A. Wender), 69 (36), 7683-7691.
- James H. Frederich, Jennifer K. Matsui, Randy O. Chang and Patrick G. Harran (2013). Substituted 2,2′-bipyrroles and pyrrolylfurans via intermediate isoxazolylpyrroles. Tetrahedron Lett., 54 (21), 2645-2647.
- James H. Frederich and Patrick G. Harran (2013). Modular Access to Complex Prodiginines: Total Synthesis of (+)-Roseophilin via its 2-Azafulvene Prototropisomer. J. Am. Chem. Soc., 135 (10), 3788-3791.
- Gelin Wang, Xiaoming Wang, Hong Yu, Shuguang Wei, Noelle Williams, Daniel L Holmes, Randal Halfmann, Jacinth Naidoo, Lai Wang, Lin Li, She Chen, Patrick G. Harran , Xiaoguang Lei, Xiaodong Wang (2013). Small-molecule activation of the TRAIL receptor DR5 in human cancer cells. Nature Chemical Biology, 9, 84-89.
- Hui Ding, Andrew Roberts, and Patrick G. Harran (2013).Total synthesis of ageliferin via acyl N-amidinyliminium ion rearrangement. Chem. Sci., 4 (1), 303-306.
- Hui Ding, Andrew Roberts, and Patrick G. Harran (2012).Synthetic (±)-Axinellamines Deficient in Halogen. Angew. Chem Intl. Ed. Engl., 51, 4340-4343.
- Rachel M. Greer, Michael Peyton, Jill E. Larsen, Luc Girard, Yang Xie, Adi Gazdar, Patrick Harran, Lai Wang, Rolf A. Brekken, Xiaodong Wang, and John D. Minna (2011) SMAC mimetic (JP1201) sensitizes non small cell lung cancers to multiple chemotherapy agents in an IAP dependent but TNFα independent manner. Cancer Research, 71, 7640-7648.
- Kenneth V. Lawson, Tristan E. Rose, and Patrick G. Harran (2011) Synthesis of a Designed Sesquiterpenoid that Forms Useful Composites with Peptides and Related Oligomers. Tetrahedron Lett., 52, 653-654.
- Charles Caldwell, Gunnar Hanson, Susan Harran, Patrick G. Harran, Qi Wei, Ming Zhou (2010) Methods for Preparing Diazonamides. US Patent #7,851,620 B2, Issued December 14, 2010.
- Patrick G. Harran, Xiaodong Wang, Jef K. De Brabander, Lin Li, Ranny Mathew Thomas, Hidetaka Suzuki (2010) Dimeric Small Molecule Potentiators of Apoptosis. US Patent #7,816,538 B2. Issued: October 19, 2010.
- Qingyi Li, Paul Hurley, Hui Ding, Andrew G. Roberts, Radha Akella, and Patrick G. Harran (2009) Exploring Symmetry-Based Logic for a Synthesis of Palau’amine. J. Org. Chem., 74, 5909-5919.
- Patrick G. Harran, Gelin Wang and Xiaodong Wang (2009) Ornithine Aminotransferase (OAT): A Target for Anticancer Drugs. US Patent #7,622,289 B2. Issued November 24, 2009.
- Patrick G. Harran, Noelle S. Williams, Anthony W.G. Burgett (2009) Diazonamide A Analog. U.S. Patent #7,538,129 B2. Issued May 26, 2009.
- Tongjin Zhao, Michael S. Brown, Joseph L. Goldstein and Patrick G. Harran (2008) Small Molecule Inhibitors of the Ghrelin O-Acyltransferase, Serial No. 61/102,353, Filed October 3, 2008.
- Hongda Zhao, Lidet Negash, Qi Wei, Thomas G LaCour, Sandi Jo Estill, Emanuela Capota, Andrew A. Pieper and Patrick G. Harran (2008) Acid Promoted Cinnamyl Ion Mobility Within Peptide Derived Macrocycles. J. Am. Chem. Soc., 130.
- Sean Petersen, Lai Wang, Asligul Yalcin-Chin, Lin Li, Michael Peyton, John Minna, Patrick Harran and Xiaodong Wang (2007) Autocrine TNFα Signaling Renders Human Cancer Cells Susceptible to Smac Mimetic-Induced Apoptosis. Cancer Cell 12. 445-456. Commentary: Smac Mimetics and TNFα: A Dangerous Laison? (2007) Cell 131, 655-658.
- Gelin Wang, Libin Zhang, Anthony Burgett, Patrick G Harran and Xiaodong Wang (2007)Diazonamide Toxins Reveal an Unexpected Function for Ornithine δ-Aminotransferase in Mitotic Cell Division. Proc. Nat. Acad. Sci. (USA) 104, 2068-2073.
- Noelle Williams, Anthony Burgett, Ashley Atkins, Xiaodong Wang, Patrick G. Harran and Steven McKnight (2007) Therapeutic Anti-Cancer Efficiacy of a Synthetic Diazonamide Analog in the Absence of Overt Toxicity Proc. Nat. Acad. Sci. (USA) 104, 2074-2079.
- Iryna Zubovych, Thomas Doundoulakis, Patrick G Harran and Michael G Roth (2006) A Missense Mutation in C.elegans Prohibitin 2 Confers an Atypical Multidrug Resistance Proc. Nat. Acad. Sci. (USA) 103, 15523-15528.
- Patrick G Harran, Jing Li, and Susan Jeong (2006) Synthetic Diazonamides as Novel Anti-Mitotic Agents. US Patent # 7,022,720 B2. Issued April 4, 2006.
- Masakazu Nakadai and Patrick G. Harran (2006) Concerning the Phakellin Substructure of Palau’amine. Tetrahedron Lett., 47, 3933-3935.
- Hugo Garrido-Hernandez, Masakazu Nakadai, Mark Vimolrantana, Qingyi Li, Thomas Doundoulakis and Patrick G. Harran (2005) Spirocycloisomerization of Tethered Alkylidene Glycocyamidines: Synthesis of a Base Template Common to Palau’amine Family Alkaloids. Angew. Chem Intl. Ed. Engl., 44, 765-769.
- Lin Li, Ranny Mathew Thomas, Hidetaka Suzuki, Jef K. De Brabander, Xiaodong Wang and Patrick G. Harran (2004) A Small Molecule Smac Mimic Potentiates TRAIL and TNFα-Mediated Cell Death Science, 305, 1471-1474.
- Anthony Burgett, Qingyi Li, Qi Wei, and Patrick G. Harran (2003) A Concise and Flexible Total Synthesis of (–)-Diazonamide A Angew. Chem Intl. Ed. Engl., 42, 4961-4966.
- Qi Wei, Susan Harran, and Patrick G. Harran (2003) Methods to Initiate Synthetic Re-Structuring of Peptides Tetrahedron (symposium-in-print) 59, 8947-8954.
- Zobeida Cruz-Monserrate, Jeffrey T. Mullaney, Patrick G. Harran, George R. Pettit and Ernest Hamel (2003) Dolastatin 15 Binds in the Vinca Domain of Tubulin as Demonstrated by Hummel-Dreyer Chromatography Eur. J. Biochem., 3822-3828.
- Jing Li, Susan Jeong, Lothar Esser, and Patrick G. Harran (2001) Total Synthesis of Nominal Diazonamides: Part 1. Convergent Preparation of the Structure Proposed for (–)-Diazonamide A. Angew. Chem Intl. Ed. Engl., 40, 4765-4770.
- Jing Li, Anthony Burgett, Lothar Esser, Carlos Amezcua, and Patrick G. Harran (2001) Total Synthesis of Nominal Diazonamides: Part 2. On the True Structure and Origin of Natural Isolates. A.Angew. Chem Intl. Ed. Engl., 40, 4770-4773.
- Jing Li, Xin Chen, Anthony Burgett, and Patrick G. Harran (2001) Synthetic seco Forms of (–)- Diazonamide A. Angew. Chem Intl. Ed. Engl., 40, 2682-2685.
- Xin Chen, Lothar Esser, and Patrick G. Harran (2000) Stereocontrol in Pinacol Ring-Contraction of Cyclopeptidyl Glycols: The Diazonamide C10 Problem. A.Angew. Chem Intl. Ed. Engl., 39, 937-940.
- Troy D. Ryba and Patrick G. Harran (2000) Two Useful Photolabile Surfaces for Solid Phase Synthesis. Organic Letters, 2, 851-853.
- Susan Jeong, Xin Chen, and Patrick G. Harran (1998) Macrocyclic Triarylethylenes Via Heck Endocyclization: A System Relevent To Diazonamide Synthesis.< J. Org. Chem., 63, 8640-8641.
- Paul A. Wender, Jef De Brabander, Patrick G. Harran, Juan-Miguel Jimenez, Michael F.T. Koehler, Blaise Lippa, Cheol-Min Park, Carsten Siedenbiedel and George R. Pettit (1998) The Design, Computer Modeling, Solution Structure and Biological Evaluation of Synthetic Analogs of Bryostatin 1. Proc. Natl. Acad. Sci. USA, 95, 6624-6629.
- Paul A. Wender, Jef De Brabander, Patrick G. Harran, Juan-Miguel Jimenez, Michael F.T. Koehler, Blaise Lippa, and Cheol-Min Park (1998) Synthesis of the First Members of a New Class of Biologically Active Bryostatin Analogs. J. Am. Chem. Soc., 120, 4534-4535.
- Paul A. Wender, Yolanda Martin-Cantalejo, Andrew J. Carpenter, Anna Chiu, Jef De Brabander, Patrick G. Harran, Juan-Miguel Jimenez, Michael F.T. Koehler, Blaise Lippa, James A. Morrison, Stephen G. Müller, Stephen N. Müller, Cheol-Min Park, Makoto Shiozaki, Carsten Siedenbiedel, Donald J. Skalitzky, Masahiro Tanaka, and Kazuhiro Irie (1998) The Chemistry-Medicine Continuum: Synthetic, Computer, Spectroscopic, and Biological Studies on New Chemotherapeutic Leads. Pure & Applied Chem., 70, 539-546.
- Paul A. Wender, Jef De Brabander, Patrick G. Harran, Kevin W. Hinkle, Blaise Lippa, and George R. Pettit (1998)Synthesis and Biological Evaluation of Fully Synthetic Bryostatin Analogs. Tetrahedron Lett., 39, 8625-8628.
- Patrick G. Harran and Paul A. Wender: Condensation and Commentary (1997) Alkynylation of C-H Bonds Via Reaction With Acetylenic Triflones.Chemtracts – Organic Chemistry, 522-526.
- Frederick E. Ziegler and Patrick G. Harran (1995) A Synthesis of Naturally Occurring (1S,2S,3R)- 4-Hydroxymethylcyclopent-4-ene-1,2,3-triol Utilizing the Cyclization of a Dioxolanyl Radical. SynLett (Special Issue Dedicated to Professor Gilbert Stork), 493-495.
- Frederick E. Ziegler and Patrick G. Harran (1993) A Route to Chiral Epoxypyrroloindoles via Oxiranyl Radical Cyclization. Tetrahedron Lett., 34, 4505-4508.
- Frederick E. Ziegler and Patrick G. Harran (1993) Intramolecular Addition of a Dioxolanyl Radical to the Indole Nucleus: Preparation of Enantiomerically Pure, Oxygenated Perhydro -3Hpyrrolo[ 1,2a]indoles. J. Org. Chem., 58, 2768-2773.
- Patrick G. Harran, Blanca O. Lopez and Raymond J. Giguere (1990) Synthetic Application of the Alder-Bong Reaction: Stereoselective Construction of the Methanohydroazulene Framework. Syn. Commun, 20, 1453-1462.