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Faculty and Staff Profiles

Mahesh Lakshman

Professor

School/Division

Division of Science

Department

Chemistry

Affiliated Departments

Research Center in Minority Institutions

Office

Marshak 1235

  • Profile

    Prof. Lakshman obtained the PhD degree from the University of Oklahoma and did postdoctoral work as a Fogarty Fellow at the National Institutes of Health (NIDDK).  He then took up an industrial position as Senior Scientist before returning to academia 1998.  Prof. Lakshman started his academic career at the University of North Dakota before joining CCNY. From 2008-2011, Prof. Lakshman was the Executive Officer for the CUNY PhD program in Chemistry.
  • Education

    B.Sc. University of Bombay
    M.Sc. University of Bombay
    MS University of Oklahoma
    PhD University of Oklahoma
    Postdoctoral Research at the National Institutes of Health
  • Courses Taught

    Chemistry 261 (Undergraduate, Organic Chemistry 1, lecture)
    Chemistry 262 (Undergraduate, Organic Chemistry 1, laboratory)
    Chemistry 210 (Undergraduate, Applied Chemistry for Biomedical Engineers, lecture, partial)
    Chemistry B5000 (Masters, Organic Mechanisms, lecture)
    Chemistry B5100 (Masters, Organic Synthesis, lecture)
    Chemistry B5100 (Masters, Spectroscopy and Structural Proof in Organic Chemistry, lecture)
    Chemistry U75000 (PhD, Advanced Organic Chemistry I, lecture)
    Chemistry U75100 (PhD, Advanced Organic Chemistry II, lecture)
    Chemistry U80511 (PhD, Organic Seminar)





  • Research Interests

    Prof. Lakshman's research is in organic chemical synthesis pertaining to questions of biological interest.  The program has many facets but can be broadly divided into the following areas.

    A. Nucleoside Modifications. Here new metal-catalyzed as well as uncatalyzed routes are being invented, to enable nucleoside modification.

    B. Studies on Environmental Pollutants. In this area, structural and biological effects of DNA modification by environmental pollutants are studied.  In addition, new chemical methodology to create model systems for studying metabolic activation processes of environmental pollutants are being developed.

    C. New Chemical Methodology. New methods to create molecules, and new physiologically important molecules are developed, via new approaches.

    Research is conducted with the idea that Fundamental Understanding drives New Chemistry (FUNCy).  Thus, development of chemical methodology and synthesis of novel molecules require a sound understanding of mechanistic organic chemistry, as being integral to the research.

    Prof. Lakshman's research programs have been funded by:
    The National Institutes of Health (National Cancer Institute, National Institute of General Medical Sciences, National Institute of Allergy and Infectious Diseases), 2000-2014.

    The National Science Foundation (2003-2017).

    Prof. Lakshman maintains several active collaborations in the US and internationally.

  • Publications

    Representative Recent Publications (2009-)

    Gurram. V.; Akula, H. K.; Garlapati, R.; Pottabathini, N.; Lakshman, M. K.: Mild and general access to diverse 1H-benzotriazoles via diboron mediated N–OH deoxygenation, and Pd-catalyzed C–C and C–N bond formation, Advanced Synthesis and Catalysis 2014, accepted for publication.

    Yedulla, V. R.; Pradhan, P.; Yang, L.; Lakshman, M. K.: Cycloaddition of arynes and cyclic enol ethers as a platform for access to stereochemically defined 1,2-disubstituted benzocyclobutenes, European Journal of Organic Chemistry 2014, accepted for publication.

    Lakshman, M. K.; Singh, M. K.; Kumar, M.; Chamala, R. R.; Yedulla, V. R.; Wagner, D.; Leung, E.; Yang. L.; Matin, A.; Ahmad, S.: Facile synthesis of 1-alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents, mechanistic studies, and synthetic applications, Beilstein Journal of Organic Chemistry 2014, 10, 1919–1932.  DOI: 10.3762/bjoc.10.200

    Chamala, R. R.; Parrish, D.; Pradhan, P.; Lakshman, M. K.: Purinyl N1-directed C-H oxidation in 6-arylpurines and 6-arylpurine nucleosides, Journal of Organic Chemistry 2013, 78, 7423-7435.  DOI: 10.1021/jo4008282

    Akula, H. K.; Lakshman, M. K.: Synthesis of deuterated 1,2,3-triazoles, Journal of Organic Chemistry 2012, 77, 8896-8904.  DOI: 10.1021/jo301146j

    Lakshman, M. K.; Kumar, A.; Balachandran, R.; Day, B. W.; Andrei, G.; Snoeck, R.; Balzarini, J.: Synthesis and biological properties of C-2 triazolyl inosine derivatives, Journal of Organic Chemistry 2012, 77, 5870-5883.  DOI: 10.1021/jo300628y
    Editor selected featured article in the issue

    Gurram, V.; Pottabathini, N.; Garlapati, R.; Chaudhary, A. B.; Patro, B.; Lakshman, M. K.: C-C cross-coupling reactions of O6-alkyl-2-haloinosine derivatives and a one-pot cross-coupling/O6-deprotection procedure, Chemistry-An Asian Journal, 2012, 7, 1853-1861.  DOI: 10.1002/asia.201200093
    Featured on the front cover of the issue

    Kokatla, H. P.; Lakshman, M. K: Two-step, one-pot synthesis of inosine, guanosine, and 2'-deoxyguanosine O6-ethers, Current Protocols in Nucleic Acid Chemistry (John Wiley and Sons, Inc.) 2012, 49, 1.26.1-1.26.16.  DOI: 10.1002/0471142700.nc0126s49

    Lakshman, M. K.; Deb, A.; Chamala, R. R.; Pradhan, P.; Pratap, R.: Direct arylation of 6-phenylpurine and 6-arylpurine nucleosides by ruthenium-catalyzed C-H bond activation, Angewandte Chemie, International Edition 2011, 50, 11400-11404. DOI: 10.1002/anie.201104035
    Featured on the inside cover of the issue

    Kokatla, H. P.; Thomson, P. F.; Bae, S.; Facile reduction of amine N-oxides by diboron compounds, Journal of Organic Chemistry 2011, 76, 7842-7848. DOI: 10.1021/jo201192c

    Kokatla, H. P.; Lakshman, M. K.: One-pot etherification of purine nucleosides and pyrimidines, Organic Letters 2010, 12, 4478-4881. DOI: 10.1021/ol101655h

    Thomson, P. F.; Lagisetty, P.; Balzarini, J.; De Clercq, E.; Lakshman, M. K.: Palladium-catalyzed aryl amination reactions of 6-bromo and 6-chloropurine nucleosides, Advanced Synthesis and Catalysis 2010, 352, 1728-1735. DOI: 10.1002/adsc.200900728

    Kumar, A.; Akula, H. K.; Lakshman, M. K.: Simple synthesis of amides and Weinreb amides using PPh3 or polymer-supported PPh3 and iodine, European Journal of Organic Chemistry 2010, 2709-2715. DOI: 10.1002/ejoc.200901420
    Highlighted in Synfacts 2010, #8, 968

    Lakshman, M. K.; Singh, M. K.; Parrish, D.; Balachandran, R.; Day, B. W.: Azide-tetrazole equilibrium of C-6 azidopurine nucleosides and their ligation reactions with alkynes, Journal of Organic Chemistry 2010, 75, 2461-2473. DOI: 10.1021/jo902342z

    Pratap, R.; Parrish, D.; Gunda, P.; Venkatraman, D. V.; Lakshman, M. K.: Influence of biaryl phosphine structure on C-N and C-C bond formation, Journal of the American Chemical Society 2009, 131, 12240-12249.

    Lakshman, M. K.; Frank, J.: A simple method for C-6 modification of guanine nucleosides, Organic and Biomolecular Chemistry 2009, 7, 2933-2940. DOI: 10.1039/B905298D
    Featured on the cover of the issue

    Singh, M. K.; Lakshman, M. K.: A simple synthesis of nitriles from aldoximes, Journal of Organic Chemistry 2009, 74, 3079-3084. DOI: 10.1021/jo900100v
    Among the "Top 20 most downloaded articles for the previous month" (April 2009)
    Highlighted in ChemInform 2009, 40, doi: 10.1002/chin.200935087

    Bae, S.; Chaturvedi, S.; Lakshman, M. K.: O6-(Benzotriazol-1-yl)inosine derivatives, a new class of compounds for modification at the C-6 of purine nucleosides, Current Protocols in Nucleic Acid Chemistry (John Wiley and Sons, Inc.) 2009, Supplement 36, 1.22.

    Lakshman, M. K.; Choudhury, A.; Bae, S.; Rochttis, E.; Pradhan, P.; Kumar, A.: Synthesis of N6,N6-dialkyl adenine nucleosides using hexaalkylphosphorus triamides produced in situ, European Journal of Organic Chemistry, 2009, 152-159. DOI: 10.1002/ejoc.200800752

  • Additional Information

    Awards and Recognitions

    Recipient of a 2014 Japan Society for the Promotion of Science Fellowship.

    Visiting Professor, Indian Institute of Technology, Bombay, September-November 2013

    "In Honor of Outstanding Scholarly Achievements and Contributions to the Creation and Transmittal of Knowledge" Certificate of Recognition from the City University of New York, 2012

    The City College of New York President's S.T.A.R. (Service, Teamwork, Action, and Results) Award 2011

    "Excellent Service to the Editors and Authors of EurJOC European Journal of Organic Chemistry" Certificate of Recognition from Wiley-VCH and ChemPubSoc Europe

    "In Honor of Outstanding Scholarly Achievements to the Creation and Transmittal of Knowledge" Certificate of Recognition from The City University of New York, 2007

    Certificate of Appreciation from the Alfred P. Sloan Foundation for "Commitment to Advancing Underrepresented Minority Students in Mathematics, Science and Engineering and for Partnering with the Foundation's Minority Program," 2007

    Profiled in the June 1 issue of India Abroad, 2007

    "For Securing Major Institutional Grant Funds in 2005" Certificate of Recognition from The City University of New York, 2006

    "In Honor of Outstanding Scholarly Achievements to the Creation and Transmittal of Knowledge" Certificate of Recognition from The City University of New York, 2004

    "Outstanding Mentor Award" The City College of New York, 2003-2004

    "In Honor of Outstanding Scholarly Achievements to the Creation and Transmittal of Knowledge" Certificate of Recognition from The City University of New York, 2002

    "In Honor of Outstanding Scholarly Achievements to the Creation and Transmittal of Knowledge" Certificate of Recognition from The City University of New York, 2001

    Professional Service

    International Advisory Board Member, 21st Indian Society of Chemists and Biologists International Conference, Lucknow, India, 2015.
    Co-Chair Oral Presentation Session at the 19th Indian Society of Chemists and Biologists International Conference, Udaipur, India, 2013.
    Co-Chair Lecture Session at the Frontiers in Pharmaceutical Sciences: Global Perspectives (International Conference), University of Rhode Island, 2012.
    Co-Chair Oral Presentation Session at the 14th Indian Society of Chemists and Biologists International Conference, Lucknow, India, 2010.
    Editorial Board Member Organic Chemistry International.
    Editorial Board Member Current Chemical Biology.
    Editorial Board Member Acta Chimica Slovenica.
    Ad hoc and Panel Reviewer for The National Institutes of Health, The National Science Foundation, The American Chemical Society Petroleum Research Fund.

    Reviewer for various national and international journals (for example: Angewandte Chemie, International Edition, Journal of the American Chemical Society, Nature Protocols, Organic Letters, The Journal of Organic Chemistry, The Journal of Medicinal Chemistry, European Journal of Organic Chemistry, ChemCatChem, RSC Advances, Chemical Research in Toxicology, Bioorganic and Medicinal Chemistry, Bioorganic and Medicinal Chemistry Letters, Tetrahedron, Tetrahedron Letters, Synthesis, Synlett)

    Administrative Service

    Vice Chair, Department of Chemistry, The City College of New York
    Member of the Graduate Admissions Committee
    Executive Officer, The City University of New York PhD Program in Chemistry, July 2008-June 2011
    Chair, Masters Program Committee
    Chair, Search Committee for a Lecturer in Organic Chemistry
    Chair, Search Committee for a Faculty Member in Organic Chemistry
    Member, Outstanding Teaching/Mentoring Award Committee
    Member, Search Committee for a Faculty Member in Organic Chemistry
    Member, Search Committee for Organic and Biochemistry Technicians
    Member, Executive Committee of the Chemistry Department
    Member, Search Committee for NMR Facility Manager

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