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Pakamas Tongcharoensirikul Jenkins
Department of Chemistry
College of Arts and Sciences
102 Hurtig Hall, 360 Huntington Avenue
Northeastern University
Boston, MA 02115
Key Words
Education; Synthetic Organic Chemistry; Biochemistry; Organic Photochemistry; Analytical Instruments; NMR Spectrometer; Mass Spectrometer; Molecular modeling.
Objective
A teaching position or a challenging research position in synthetic organic chemistry; biochemistry; organic photochemistry; or polymer chemistry or in the fields of NMR Spectrometer or Mass Spectrometer.
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October 1999-Present
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Postdoctoral fellow
Department of Pharmaceutical Sciences
The University of Montana
Missoula, MT 59812
awarded by
The American Heart Association
Research:
1. Asymmetric Synthesis of alpha-Amino Phosphonothioic Acid
2. Synthesis of Boronic Acid Derivatives as Glutamate Vesicular
Transporter and Receptor Inhibitor Analogs
Advisor:
Professor Charles M. Thompson, Ph.D.
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August 1990-February 1999
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Ph.D. Organic Chemistry
Department of Chemistry and Biochemistry
Worcester Polytechnic Institute
Worcester, MA 01609
Dissertation: Photochemistry of Substituted Isothiazoles and Thiazoles
Advisor: Professor James W. Pavlik, Ph.D.
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June 1984-Nov 1987
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M.Sc. Organic Chemistry
Department of Chemistry
Chulalongkorn University , Bangkok, Thailand
M.Sc. Thesis: Copolymerization of Vinyl Acetate with Chlorinated Phenyl Acrylates
Advisor: Professor Supawan Tantayanon, Ph.D.
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June 1980-Mar 1984
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B.Sc. Chemistry
Department of Chemistry
Chulalongkorn University , Bangkok, Thailand
Senior research: Extraction and Analysis of Strychnine from the seeds of Strychnos nux vomica
Advisor: Professor Somchai Paengpreecha, Ph.D.
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fluent in English and Thai, working knowledge of Japanese.
watercolor painting, running, playing basketball, dancing.
- Skilled in multistep organic synthesis.
- Skilled in handling air sensitive reagents.
- Working knowledge of MassLynx to operate LCT (Liquid Chromatography Time of Flight Mass Spectrometer) and QTOF (Quadrupled Time of Flight Mass Spectrometer).
- Skilled in synthesis using high pressure and temperature reactor.
- Experienced in conducting biological assay involving radioactive compounds.
- Working knowledge in Proteomics and Genomics including protein sequencing by
Mass Spectrometry.
- Skilled in 200 MHz and 400 MHz Bruker FT-NMR including XWIN-NMR,
automated programs and two dimensional NMR, 400 MHz
Varian NMR ,
1600 Perkin Elmer FT-IR,
8500 and 9000 Perkin Elmer capillary GC, Hitachi U-2000 Spectrophotometer,
Perkin Elmer LS-50 Luminescence Spectrophotometer, Hewlett Packard GC-MS.
- Familiar with molecular modeling programs, i.e., PCMODEL, MOPAC, HYPERCHEM, PCSPARTON, SYBYL.
- Skilled in chromatographic separation techniques, i.e., TLC, Preparative TLC, HPTLC, flash column chromatography, HPLC.
- Skilled in use of MacIntosh and Power PC MacIntosh Systems, IBM and IBM compatible systems.
- Skilled in use of Microsoft Windows ME and Microsoft Windows NT, Chem Office, Lab-Calc Data manipulation.
- Working knowledge of MS-DOS, UNIX and IRIX operating systems.
- Working knowledge of computer programming and languages:
C, C++ , FORTRAN, BASIC.
- Skilled in use of HTML.
- Competent on scientific and artistic glass blowing, i.e., fixing vacuum line, making snoopy, glass roses.
- Competent on mechanical and electrical repairing of instruments and appliances, i.e., NMR, UV, IR spectrophotometers, GC, HPLC, mechanical pumps, cars.
- Techniques of polymer syntheses and characterizations, i.e., viscosity and glass transition temperature (tg).
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October 1999-Present
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A Postdoctoral fellow at The University of Montana
Research Project:
1. alpha Amino Phosphonothioic Acid
2. Glutamate Vesicular Transporter and Receptor Inhibitor
Advisor: Professor Charles M. Thompson, Ph.D.
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May 1999-September 1999
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An Instructor at Department of Chemistry, Srinakarinwirot University
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January 1999-May 1999
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A Researcher at Department of Chemistry, Chulalongkorn University
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August 1996-May 1998
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An Instructor at Department of Chemistry and Biochemistry, WPI
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August 1990-May 1996
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A Teaching Assistant at Department of Chemistry and Biochemistry, WPI
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September 1989-August 1990
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A Researcher at Kyoto University, Kyoto, Japan
Research Project: Ruthenium Complex Catalyst of C-H Insertion
Advisor: Professor Yoshihisa Watanabe, Ph.D.
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May 1988-September 1989
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A Researcher and an instructor for petrochemistry and spectroscopy courses (junior and senior theoretical courses)
Petroleum and Petrochemical College,
Chulalongkorn University, Bangkok, Thailand.
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May 1984-September 1989
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An analyst at K. Kosmic Holding Co., Ltd., Bangkok, Thailand
Quality control of products such as mouth wash, propylene oxide, malt in beer manufacturing.
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June 1999
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Chemical Safety: Management Incidents in University
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June 2000-November 2001
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The American Heart Association Postdoctoral Fellowship Award
The proposal was written by Pakamas and was awarded "$62400"
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February 2003-present
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The Army Medical Research Postdoctoral Fellowship Award
The proposal was written by Pakamas and was awarded "$98000"
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1999
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Sigma Xi Ph.D. Research Award Nomination
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1995
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The American Institute of Chemist Graduate Student Award
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1994
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Teaching Assistant of The Year Award, Worcester Polytechnic Institute
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1993
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Phi Lambda Upsilon, National Honorary Chemical Society
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- J. W. Pavlik and P. Tongcharoensirikul, "Phototransposition Chemistry of
Phenylisothiazoles and Phenylthiazoles," Paper No. 126, 22nd Northeast Regional
Meeting of the American Chemical Society, Syracuse, NY, June 22 1992.
- J. W. Pavlik, C. R. Pandit and Pakamas Tongcharoensirikul, "Phototransposition
Chemistry of the Thiazole-Isothiazole Heterocyclic System," Poster No. 192,
14th IUPAC Symposium on Photochemistry, K. U. Leuven, Leuven, Belgium, July 19-25, 1992.
- J. W. Pavlik, P. Tongcharoensirikul and K. M. French, "Phototransposition Chemistry of
Phenylisothiazoles and Phenylthiazoles," Poster No. 47, 5th Inter-American Photochemical Society
Winter Conference, Clearwater Beach, FL, January, 1993.
- J. W. Pavlik, P. Tongcharoensirikul and K. M. French, "Phototransposition Chemistry of the
Phenylisothiazole-Phenylthiazole System," Poster No. 193, 23 rd Northeast Regional Meeting of
the American Chemical Society, Boston, MA, June 24, 1993.
- J. W. Pavlik, P. Tongcharoensirikul and K. M. French, "Phototransposition Mechanisms for
Phenylisothiazoles and Phenylthiazoles in Benzene Solvent," Paper No. 270, 206th National Meeting
of the American Chemical Society, Chicago, IL, August 25, 1993.
- J. W. Pavlik, P. Tongcharoensirikul and K. M. French, "Phototransposition of Phenylisothiazoles,
The P4 Pathway," Paper No. 126, 24th Northeast Regional Meeting of the American Chemical Society,
Burlington, VT, June 21, 1994.
- J. W. Pavlik and P. Tongcharoensirikul, "Phototransposition Chemistry of Phenylisothiazoles and
Phenylthiazoles," Poster No. 129, 15th IUPAC Symposium on Photochemistry, Prague, Czech Republic,
July 17-22, 1994.
- J. W. Pavlik, P. Tongcharoensirikul and K. M. French, "Phototransposition Chemistry of Phenylisothiazoles,
The P4 Permutation Pathway," Poster No. 43, 7th Inter-American Photochemical Society Winter Conference,
Clearwater Beach, FL, January, 1995.
- P. Tongcharoensirikul and J. W. Pavlik, "Trapping of Nitrile and Isocyanide Intermediates in the Isothiazole to
Thiazole Phototransposition," Paper No. 275, 25th Northeast regional Meeting of the American Chemical Society,
Rochester, NY, October 21-25, 1995.
- P. Tongcharoensirikul and J. W. Pavlik, "Photochemistry of 4-Substituted Isothiazoles," Paper No. 114, 27th
Northeast Regional Meeting of the American Chemical Society, Saratoga Springs, NY, June 22-25, 1997.
- P. Tongcharoensirikul, J.A. Trautman, A.I. Suarez, and C.M. Thompson, "Stereoselective Synthesis of Substituted
alpha-Aminophosphonothionates, Northwest & Rocky Mountain ACS Joint Regional Meeting, Idaho Falls, ID, June 15-17, 2000.
- P. Tongcharoensirikul, T. Voelker, A. Suarez, and
C. M. Thompson, "Synthesis of enantioenriched APTA’s and preliminary screening as matrix metalloproteinase inhibitors" 222nd ACS National Meeting, Chicago, Illinois,
August 26-30, 2001.
- P. Tongcharoensirikul, R. Bridges and C. M. Thompson, "Boronic acid analogs as selective inhibitors of glutamate receptors and
transporters" 222nd ACS National Meeting, Chicago, Illinois,
August 26-30, 2001.
- Pavlik, J. W.; Tongcharoensirikul, P.; Bird, N. P.; Day, A. C.;
Barltrop, J. "A. Phototransposition Chemistry of Phenylisothiazoles
and Phenylthiazoles. 1.Interconversions in Benzene Solution"
J. Am. Chem. Soc. 1994, 116,
2292-2300.
- Pavlik, J. W.; Tongcharoensirikul, P.; French, K. M. "Phototransposition Chemistry of 4-Substituted Isothiazoles. The P4 Permutation Pathway" J. Org. Chem.
1998, 63, 5592-5603.
- Pavlik, J. W.; Tongcharoensirikul, P. "Photochemistry of 3- and 5-Phenylisothiazoles. Competing Phototransposition Pathways" J. Org. Chem.
2000, 65, 3626-3632.
- Trautmann, J.; Suarez, A. I.; Tongcharoensirikul, P.; Muth, G. W.; Thompson, C. M.
"A Facile Route to Substituted Dimethoxy Phosphonothionates Using Dimethyl Thiophosphite"
Phosphorus, Sulfur, and Silicon and the Related Elements manuscript accepted.
- Tongcharoensirikul, P.; Suarez, A. I.; Thompson, C. M. "Effect of Chiral Auxiliaries on the Stereoselective Addition of Dimethyl Thiophosphite to Imines" manuscript in preparation to submit to The Journal of Organic Chemistry.
- Tongcharoensirikul, P.; Fussell, K.; Williamson, D.; Voelker, T.; Thompson, C. M. "Development of A Novel Rapid High-Performance Liquid Chromatography-Mass Spectrometry Assay for Thermolysin Activity" manuscript in preparation to submit to Analytical Biochemistry.
- Tongcharoensirikul, P.; Fussell, K.; Williamson, D.; Voelker, T.; Thompson, C. M.
Goals for this year (2001)
- 2-3 publications
- ACS National Presentation in Chicago
- looking for a job that I am interested in, in chemistry field
that has emphasis in biological interest
- Professor James W. Pavlik, Ph.D.
Department of Chemistry and Biochemistry
Worcester Polytechnic Institute
100 Institute Road,
Worcester, MA 01609-2280, USA
Phone: (508)831-5283
e-mail: jwpavlik@wpi.edu
- Professor Charles, M. Thompson, Ph.D.
Department of Pharmaceutical Sciences
School of Pharmacy and Allied Health
The University on Montana,
Missoula, MT 59812-1552, USA
Phone: (406)243-4643
e-mail: cmthomp@selway.umt.edu
- Professor James P. Dittami, Ph.D.
Department of Chemistry and Biochemistry
100 Institute Road,
Worcester, MA 01609-2280, USA
Phone: (508)831-5263
e-mail: jdittami@wpi.edu
- Dr. Peter Ziegler
Northeast Office
Bruker BioSpin Corporation
15 Fortune Drive, Manning Park
Billerica, MA 01821
Phone: (978) 667-9580
Fax: (978) 667-0985
- Professor Ladislav H. Berka, Ph.D.
Department of Chemistry and Biochemistry
100 Institute Road,
Worcester, MA 01609-2280, USA
Phone: (508)831-5444
e-mail: lhberka@wpi.edu
mail to:pak_t@mailcity.com
Phenylthiazoles 1-3 and phenylisothiazoles 4-6 undergo phototransposition in benzene
solvent mainly by P5, P6, and P7 permutation pathways. 4-Phenylisothiazole (5) and 5-phenylisothiazole
(6) also transpose via a P4 permutation process to yield 4-phenylthiazole (2) and 5-phenylthiazole
(3), respectively in less than 1% yield. In benzene saturated with D2O, 2-phenylthiazole (1 and 5-phenylisothiazole
(6) each transposes to yield 4-deuterio-3-phenylisothiazole (4-D-4) and 4-phenylthiazole (2)
without deuterium incorporation. Irradiation of 4-phenylthiazole (2) under these conditions results in rapid
photodeuteration to yield 2-deuterio-4-phenylthiazole (2-D-2), which subsequently phototransposes to
5-deuterio-3-phenylisothiazole (5-D-4). These experimental results can be rationalized by a mechanism
involving initial electrocyclic ring closure and sigmatropic shift of sulfur around the four sides of the azetine ring.
Rearomatization of each bicyclic intermediate thus allows sulfur to insert into each position in the carbon-nitrogen sequence.
As a consequence, these compounds can be divided into a tetrad in which isomers 1, 2, 4, and 6
interconvert mainly via P5, P6, and P7 pathways. Within the tetrad, BC-6, the bicyclic intermediate derived
from 5-phenylisothiazole (6), is postulated to undergo deuteration with simultaneous sigmatropic shift of sulfur
when the reaction is carried out in benzene-D2O. This mechanistic view provides one coherent interpretation for the
observed phototransposition and photodeuteration reactions.
Upon irradiation in the presence of a small quantity of base, 4-substituted isothiazoles undergo photocleavage to yield
substituted cyanosulfides, which can be trapped as their benzyl thioether derivatives, and substituted isocyano sulfides.
Both products are suggested to arise via initial photocleavage of the sulfur-nitrogen bond, resulting in the formation of a
substituted b-thioformylvinyl nitrene, which can rearrange to the observed cyanosulfide, or cyclize to an undetected
thioformylazirine. Deprotonation of the azirine leads directly to the isocyanosulfide. The plight of the isocyanosulfide
depends on the C-4 substituent. If the substituent is aromatic, the isocyanosulfide is reprotonated at the isocyanide
carbon and spontaneously cyclize to a substituted thiazole, the observed transposition product. If the substituent is
aliphatic, the isocyanosulfide is reprotonated at the sulfur and the resulting species has a higher energy barrier to
cyclization. In these cases, the isocyanosulfides can be observed spectroscopically and can be trapped as their
N-formylaminobenzyl thioether derivatives.
Following is the presentation accompanying
my thesis defense.