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Rahul Bhattacharya, (Ph.D)
Department of Bio-MedicalEngineering,
Johns HopkinsUniversity Schoolof Medicine
Baltimore, MD-21231; USA
Contacts:(+1) 443-253-1760
Email:rahul.chemiit@gmail.com rbhatta6@jhu.edu
Web:http://web1.johnshopkins.edu/yaremalab/pages/lab_members.htm
http://cardiopeg.bs.jhmi.edu/Pages/Team.aspx
I am a synthetic organic chemist currently working in the area of “design and synthesis of small molecules” for screening as a “drug candidate” that
can be used for Metabolic Glyco Engineering and Translational Tissue Engineering. Resourceful and committed practitioner of organic chemistry;
have a comprehensive and strategic understanding of organic synthesis and medicinal chemistry with a good and consistent publication record.
Effective communicator in a team oriented environment and highly collaborative in nature as evidenced by many collaborative publications. Received
formal training in Glycobiology and attended many courses offered by the Johns Hopkins University, School of medicine.
Experience:
March 2010‐Present: Post‐Doctoral fellow at Johns Hopkins University, School of Medicine, Department of Biomedical Engineering,
Baltimore, MD‐21231 http://web1.johnshopkins.edu/yaremalab/pages/lab_members.htm
Research Focus: a) Synthesis of short chain fatty acid (SCFA) modified Hexosamine Core Analogs and related study
towards anticancer drug development. b) Development of new techniques for improved cell surface imaging by
synthesizing new analogs to facilitate fluorophore attachment.
Jan.2009‐ Oct.2009: Post‐Doctoral Trainee Université Joseph Fourier (http://www.ujf‐grenoble.fr/) Chimie Bioorganique, DPM‐UMR 5063
CNRS, Cedex‐9 Grenoble; France. Research Focus: Development of glucosamine-core new antibiotic involving
olefin metathesis reaction.
Summary of Research Achievements:
I have designed a biopolymer-based Drug-delivery method that was implemented for delivery of glycosphingolipid inhibitor and
improved intervention of atherosclerosis and cardiac hypertrophy was achieved. This work has recently gain attention among
research communities (see link below):
http://www.hopkinsmedicine.org/news/media/releases/nanoparticle_wrapper_delivers_chemical_that_stops_fatty_buildup_in_rodent_arteri
es
The most efficient and practical route for the synthesis of -substituted pyrroles was designed. This work was undertaken because of the
fact that pyrrole-containing compounds play crucial roles in nature and “even 150 years after its isolation and synthesis, and more
than 100 years after the classical pyrrole syntheses were developed, the synthesis of highly substituted pyrrole is anything but
straightforward” as reported in Synthesis 2007, 20, 3095.
I have developed a general synthetic method and synthesized a plethora of vinyl sulfone modified hexopyranosides; studied their reactivity
in presence of nitrogen necleophiles. The successful application of vinyl sulfone-modified carbohydrates for the introduction of amine
residue at a particular centre crucially depends on the following factors: (i) the efficiency of Michael addition of amines; (ii) the
diastereoselectivity of addition of amines. It was therefore, necessary to acquire information on the efficiency of addition of nucleophiles to
vinyl sulfone-modified carbohydrates. The information obtained was utilized for the synthesis of Isonucleosides. These ‘isonucleosides’
are promising therapeutic agents of apparently very low toxicity and some of them show strong and selective anti-cancer and anti-viral
activities.
A simple, straightforward, efficient and general method was successfully designed, for the first time in literature, to synthesize 3,4-dideoxy-
3-eno-hexopyranosyl VSM carbohydrate. This conspicuous building block was applied successfully for the synthesis of aminosugar,
branche-chain sugar and chirally pure cyclopropanated sugar.
Successful design and synthesis of short chain fatty acid modified (SCFA) hexosamine-core analogs were achieved for metabolic
glycoengineering to intercept biosynthetic pathways. The scaffold dependent activities of hexosamine-core analogs raised the
possibility to investigate their use as a versatile template for drug discovery by modulating biological activity and application in
tissue engineering. In a related context I have successfully developed of new technique for improved cell surface imaging by
synthesizing new analog to facilitate fluorophore attachment. This new analog metabolically labels cell surface and the technique thus can
be used as a detection method. Work on this project is still in progress for further tune-up.
Highlights and skills:
*Lab maintenance *Project management *Synthetic route scouring and planning *Multi‐step synthesis of small molecules *Special training in
carbohydrate chemistry and synthetic chemistry of aminosugars *Compound optimization *Nucleoside Chemistry *Human Cell culture
*Operation of 200/400/500 MHz NMR Instrument *FTIR; HPLC, MALDI‐Tof Mass etc. *X‐ray crystallography: solution of crystal structures and
refinement using SELEX program *Experienced user of search engine like SCIFINDER.
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Education:
2016: Attended “Drug Discovery Case Studies” (ME:200.707)course offered by Drug discovery Program, Johns Hopkins University
School of Medicine.
2012: Attended “Fundamentals of Glycobiology” (ME:340.709)course offered by The Johns Hopkins University School of Medicine.
2013: Attended “Techniques in Glycobiology” (ME:340.710) course offered by The Johns Hopkins University School of Medicine.
2002‐ 2008: Ph.D in Synthetic Organic Chemistry] Dept. of Chemistry (http://www.iitkgp.ac.in/), Indian Institute of Technology, Kharagpur;
W.B., India Title of the thesis: Vinyl Sulfone‐Modified Hexopyranosides: Influence of Steric Bulk and Protecting Groups on the
Reaction Patterns and Synthetic Applications
1999‐2001: M.Sc in Chemistry with organic Chemistry specialization, Department of Chemistry (http://www.jaduniv.edu.in/), Jadavpur
University, Kolkata; W.B., India
1996‐1999: B.Sc Chemistry Honors, Burdwan University (http://www.buruniv.ac.in/), W. B., India
Professional Activities and Service:
2012-present: Member of American Chemical Society
2013-present: Teammember: Programof Excellence in Glycobiology (PEG) http://cardiopeg.bs.jhmi.edu/Pages/Team.aspx
2015‐present: Reviewer: ArkivocJournal(http://www.arkat-usa.org/arkivoc-journal/members-editorial-board-of-referees/)
2015‐present: Reviewer &Editorialtem member: SM journals, Annals of Chromatography and Separation Techniques
(http://www.smjournals.com/index.php/chromatography/about/editorialTeam)
2016‐present: Reviewer, ACSChemicalEducation
2016‐present: Tetrahedron (Elsevier)
2016‐present: Bioorganic& Medicinal Chemistry Letters (Elsevier)
2016‐present: Tetrahedron Letters(Elsevier)
Honors and Awards:
2009: Received Indo‐French collaborative research fellowship under ARCUSprogram.
2004‐2008: Senior Research Fellowship (SRF), CSIR‐NewDelhi, India
2002‐2004: Junior Research Fellowship (JRF), IIT‐Kharagpur, WestBengal, India
2002: Qualified in National Eligibility Test (NET) for Lectureship and research in Chemical Science. In the same year received
Council of Scientific and Industrial Research, India (CSIR) fellowship for conducting research that lead to PhD thesis.
Selected Publications: For a complete list please visit: https://scholar.google.com/citations?hl=en&user=Y9E4evEAAAAJ
1. Sanki, A. K.; Bhattacharya, R.; Atta, A. K.; Suresh, C. G.; Pathak, T. Tetrahedron, 2008, 64, 10406-10416. Diastereoselective addition of planar N-
heterocycles to vinyl sulfone-modified carbohydrates: a new route to isonucleosides.
2. Bhattacharya, R.; Atta, A. K.; Dey, D.; Pathak, T. J. Org. Chem. 2009, 74(2), 669-674. Densely Functionalized Chiral Pyrroles from Endocyclic,
Exocyclic and Acyclic Vinyl Sulfone-modified Carbohydrates.
3. Bhattacharya, R.; Dey, D.; Pathak, T. Eur. J. Org. Chem, 2009, 30, 5255-5260. Vinyl Sulfone-Modified Hex-3-Enopyranosides: Novel Routes to C3-C4
and C4-C5 Cyclopropanated Hexopyranosides.
4. Bhattacharya, R.; Pathak, T. Carbohydr. Res., 2009, 344 (17), 2336-2341. Addition of Amines and Carbon Nucleophiles to Vinyl Sulfone-modified 6-
Deoxy-hex-3-enopyranoside: A Case of Nucleophile Dependent Diastereoselectivity.
5. Bhattacharya, R.; Kesharwani, M. K.; Manna, C.; Ganguly, B.; Suresh, C. G.; Pathak, T. J. Org. Chem. 2010, 75(2), 303-314. An Experimental and
TheoreticalStudy on the Remarkable Influence of ProtectingGroups on the Selectivity of Addition of Amines to Vinyl Sulfone-modified Hex-2-
enopyranosides.
6. Pathak T, Bhattacharya, R ; Comptes Rendus Chimie, 2011, 14, 327-342. An insight into our research on vinyl sulfone-modified pyranosides and
furanosides.
7. Almaraz, R.T., Aich, U., Khanna, H.S., Tan, E., Bhattacharya, R., Shah, S. & Yarema, K.J.; Biotechnology & Bioengineering, 2012, 109, 992-1006.
Metabolic oligosaccharide engineering with N-acyl functionalized ManNAc analogues: cytotoxicity, metabolic flux, and glycan-display considerations.
8. S. Chatterjee S. Mishra , D. Bedja C. Amuzie, C.A. Foss d , M.G. Pomper , R. Bhattacharya , K.J. Yarema.; Improved intervention of atherosclerosis and
cardiac hypertrophy through biodegradable polymer-encapsulated delivery of glycosphingolipid inhibitor.; Biomaterials, 2015, 64, 125-135.
9. Kim Chaekyu, Jeon Ok Hee, Kim Do Hun, Chae JJeremy, ShoresLucas, Bernstein Nicholas, Bhattacharya Rahul, Coburn Jeannine M, Yarema Kevin J,
Elisseeff Jennifer H.; Local delivery of a carbohydrate analog forreducingarthritic inflammationand rebuilding cartilage.; Biomaterials, 2016, 83, 93-
101.