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Mahesh Lakshman
Title Investigator
Faculty Rank Professor
Degree PhD
Institution City College, CUNY
Department Chemistry
Clusters Cancer
HIV/AIDS
Infectious and Immunological Diseases
Address
The City College of New York
Department of Chemistry
160 Convent Avenue
City New York
State NY
Postal Code 10031
Telephone 212-650-7835
Fax 212-650-6107
Email
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Awards and Honors icon

2001 City University of New York In honor of Outstanding Scholarly Achievements
2002 City University of New York In honor of Outstanding Scholarly Achievements
2003 City College of New York Outstanding Mentor Award
2003 City University of New York Recipients of Major Institutional Grants for Public Service
2004 City University of New York In honor of Outstanding Scholarly Achievements
2006 City University of New York For Securing Major Institutional Grant Funds in 2005
2007 City University of New York In honor of Outstanding Scholarly Achievements
2011 City College of New York City College Presidential S.T.A.R. Award
2011 Wiley-VCH and ChemPubSoc Europe Excellent service to the Editors and Authors of EurJOC European Journal of Organic Chemistry
2012 City University of New York In honor of Outstanding Scholarly Achievements
2013 Indian Institute of Technology, Bombay (Sept 2013-Nov 2013) Visiting Professor
2014 City University of New York In honor of Outstanding Scholarly Achievements
2014 Japan Society for the Promotion of Science Fellowship
2016 Royal Society of Chemistry Elected Fellow
2017 Recognition as Albert Nelson Marquis Lifetime Achievement Award

Narrative icon

  Background

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.

Research

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. Because nucleosides are highly important in biochemistry, biology, and in medicine, many new methodology is developed and compounds are being synthesized to address biological questions such as design of antiviral and anticancer agents.

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 chemical methods to create novel molecules, and new physiologically important molecules are developed.

Thus, development of chemical methodology and synthesis of novel molecules require a sound understanding of mechanistic organic chemistry, as being integral to the research.

NIH Awarded Grants icon

  Research projects funded by the National Institutes of Health (NIH), the Centers for Disease Control (CDC), the Food and Drug Administration (FDA), and the Department of Veterans Affairs (VA)

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1.
2012Synthetic Methodology to Access Novel Antivirals5R21AI094545-02
2.
2011Synthetic Methodology to Access Novel Antivirals1R21AI094545-01
3.
2010Synthesis and Studies of Site-Specific Carcinogen-DNA Lesions5S06GM008168-30
4.
2009Synthesis and Studies of Site-Specific Carcinogen-DNA Lesions5S06GM008168-29
5.
2008Synthesis and Studies of Site-Specific Carcinogen-DNA Lesions5S06GM008168-28
6.
2007Synthesis and Studies of Site-Specific Carcinogen-DNA Lesions2S06GM008168-27
7.
2004Palladium Catalyzed C-N, C-C and C-O Bond Formation: Novel Nucleoside Structures3S06GM008168-24S1
8.
2001Regio/stereochem defined, diol epoxide adducted ras1R15CA094224-01

Publications icon

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1. Satishkumar S, Lakshman MK. Benzimidazopurine nucleosides from N6-aryl adenosine derivatives by PhI(OAc)2-mediated C-N bond formation, no metal needed. Chem Commun (Camb). 2017 Feb 14; 53(14):2226-2229.
2. Akula HK, Kokatla H, Andrei G, Snoeck R, Schols D, Balzarini J, Yang L, Lakshman MK. Facile functionalization at the C4 position of pyrimidine nucleosides via amide group activation with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and biological evaluations of the products. Org Biomol Chem. 2017 Feb 01; 15(5):1130-1139.
3. Akula HK, Kokatla H, Andrei G, Snoeck R, Schols D, Balzarini J, Yang L, Lakshman MK. Correction: Facile functionalization at the C4 position of pyrimidine nucleosides via amide group activation with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and biological evaluations of the products. Org Biomol Chem. 2017 Feb 01; 15(5):1268.
4. Lakshman MK, Tine FA, Khandaker TA, Basava V, Agyemang NB, Benavidez MSA, Gaši M, Guerrera L, Zajc B. KHF2, a mild and selective desilylating agent for phenol t-butyldimethylsilyl (TBDMS) ethers. Synlett. 2017 Mar; 28(3):381-385.
5. Basava V, Yang L, Pradhan P, Lakshman MK. A novel bis(pinacolato)diboron-mediated N-O bond deoxygenative route to C6 benzotriazolyl purine nucleoside derivatives. Org Biomol Chem. 2016 Aug 07; 14(29):7069-83.
6. Singh MK, Akula HK, Satishkumar S, Stahl L, Lakshman MK. Ruthenium-Catalyzed C-H Bond Activation Approach to Azolyl Aminals and Hemiaminal Ethers, Mechanistic Evaluations, and Isomer Interconversion. ACS Catal. 2016 Mar 04; 6(3):1921-1928.
7. Singh MK, Lakshman MK. Diarylmethanes through an Unprecedented Palladium-Catalyzed C-C Cross-Coupling of 1-(Aryl)methoxy-1 H-Benzotriazoles with Arylboronic Acids. ChemCatChem. 2015 Dec 14; 7(24):4156-4162.
8. Satishkumar S, Vuram PK, Relangi SS, Gurram V, Zhou H, Kreitman RJ, Martínez Montemayor MM, Yang L, Kaliyaperumal M, Sharma S, Pottabathini N, Lakshman MK. Cladribine Analogues via O6-(Benzotriazolyl) Derivatives of Guanine Nucleosides. Molecules. 2015 Oct 09; 20(10):18437-63.
9. Satishkumar S, Vuram PK, Relangi SS, Gurram V, Zhou H, Kreitman RJ, Montemayor MM, Yang L, Kaliyaperumal M, Sharma S, Pottabathini N, Lakshman MK. Cladribine Analogues via O6-(Benzotriazolyl) Derivatives of Guanine Nucleosides. Molecules. 2015 Oct 09; 20(10):18437-63.
10. Thomson PF, Parrish D, Pradhan P, Lakshman MK. Modular, Metal-Catalyzed Cycloisomerization Approach to Angularly Fused Polycyclic Aromatic Hydrocarbons and Their Oxidized Derivatives. J Org Chem. 2015 Aug 07; 80(15):7435-46.
11. Gurram V, Akula HK, Garlapati R, Pottabathini N, Lakshman MK. Mild and General Access to Diverse 1H-Benzotriazoles via Diboron-Mediated N-OH Deoxygenation and Palladium-Catalyzed C-C and C-N Bond Formation. Adv Synth Catal. 2015 Feb 09; 357(2-3):451-462.
12. Yedulla VR, Pradhan P, Yang L, Lakshman MK. Cycloaddition of Arynes and Cyclic Enol Ethers as a Platform for Access to Stereochemically Defined 1,2-Disubstituted Benzocyclobutenes. European J Org Chem. 2015 Feb; 2015(4):750-764.
13. Lakshman MK, Singh MK, Kumar M, Chamala RR, Yedulla VR, 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 J Org Chem. 2014; 10:1919-32.
14. Chamala RR, Parrish D, Pradhan P, Lakshman MK. Purinyl N1-directed aromatic C-H oxidation in 6-arylpurines and 6-arylpurine nucleosides. J Org Chem. 2013 Aug 02; 78(15):7423-35.
15. Soujanya S, Lakshman M, Kumar AA, Reddy AG. Evaluation of the protective role of vitamin C in imidacloprid-induced hepatotoxicity in male Albino rats. J Nat Sci Biol Med. 2013 Jan; 4(1):63-7.
16. Akula HK, Lakshman MK. Synthesis of deuterated 1,2,3-triazoles. J Org Chem. 2012 Oct 19; 77(20):8896-904.
17. Lakshman MK, Kumar A, Balachandran R, Day BW, Andrei G, Snoeck R, Balzarini J. Synthesis and biological properties of C-2 triazolylinosine derivatives. J Org Chem. 2012 Jul 20; 77(14):5870-83.
18. Kokatla HP, Lakshman MK. Two-step, one-pot synthesis of inosine, guanosine, and 2'-deoxyguanosine O6-ethers via intermediate O6-(benzotriazol-1-yl) derivatives. Curr Protoc Nucleic Acid Chem. 2012 Jun; Chapter 1:Unit1.26.
19. Gurram V, Pottabathini N, Garlapati R, Chaudhary AB, Patro B, Lakshman MK. C-C cross-coupling reactions of O6-alkyl-2-haloinosine derivatives and a one-pot cross-coupling/O6-deprotection procedure. Chem Asian J. 2012 Aug; 7(8):1853-61.
20. Lakshman MK, Deb AC, Chamala RR, Pradhan P, Pratap R. Direct arylation of 6-phenylpurine and 6-arylpurine nucleosides by ruthenium-catalyzed C-H bond activation. Angew Chem Int Ed Engl. 2011 Nov 25; 50(48):11400-4.
21. Kokatla HP, Thomson PF, Bae S, Doddi VR, Lakshman MK. Reduction of amine N-oxides by diboron reagents. J Org Chem. 2011 Oct 07; 76(19):7842-8.
22. Kokatla HP, Lakshman MK. One-pot etherification of purine nucleosides and pyrimidines. Org Lett. 2010 Oct 15; 12(20):4478-81.
23. Thomson PF, Lagisetty P, Balzarini J, De Clercq E, Lakshman MK. Palladium-Catalyzed Aryl Amination Reactions of 6-Bromo- and 6-Chloropurine Nucleosides. Adv Synth Catal. 2010 Jul 05; 352(10):1728-1735.
24. Kumar A, Akula HK, Lakshman MK. Simple Synthesis of Amides and Weinreb Amides via Use of PPh3 or Polymer-Supported PPh3 and Iodine. European J Org Chem. 2010 May; 2010(14).
25. Lakshman MK, Singh MK, Parrish D, Balachandran R, Day BW. Azide-tetrazole equilibrium of C-6 azidopurine nucleosides and their ligation reactions with alkynes. J Org Chem. 2010 Apr 16; 75(8):2461-73.
26. Pratap R, Parrish D, Gunda P, Venkataraman D, Lakshman MK. Influence of biaryl phosphine structure on C-N and C-C bond formation. J Am Chem Soc. 2009 Sep 02; 131(34):12240-9.
27. Lakshman MK, Frank J. A simple method for C-6 modification of guanine nucleosides. Org Biomol Chem. 2009 Jul 21; 7(14):2933-40.
28. Singh MK, Lakshman MK. A simple synthesis of nitriles from aldoximes. J Org Chem. 2009 Apr 17; 74(8):3079-84.
29. Bae S, Chaturvedi S, Lakshman MK. O6-(benzotriazol-1-yl)inosine derivatives for C6 modification of purine nucleosides. Curr Protoc Nucleic Acid Chem. 2009 Mar; Chapter 1:Unit 1.22.
30. Lakshman MK, Choudhury A, Bae S, Rochttis E, Pradhan P, Kumar A. Synthesis of N6 ,N6-Dialkyl Adenine Nucleosides With In Situ Formed Hexaalkylphosphorus Triamides. European J Org Chem. 2009 Jan 01; 2009(1):152-159.
31. Bae S, Lakshman MK. Synthetic utility of an isolable nucleoside phosphonium salt. Org Lett. 2008 Jun 05; 10(11):2203-6.
32. Bae S, Lakshman MK. A novel polymer supported approach to nucleoside modification. J Org Chem. 2008 May 16; 73(10):3707-13.
33. Bae S, Lakshman MK. Unusual deoxygenation and reactivity studies related to O6-(benzotriazol-1-yl)inosine derivatives. J Org Chem. 2008 Feb 15; 73(4):1311-9.
34. Bae S, Mah H, Chaturvedi S, Jeknic TM, Baird WM, Katz AK, Carrell HL, Glusker JP, Okazaki T, Laali KK, Zajc B, Lakshman MK. Synthetic, crystallographic, computational, and biological studies of 1,4-difluorobenzo[c]phenanthrene and its metabolites. J Org Chem. 2007 Sep 28; 72(20):7625-33.
35. Kang SB, De Clercq E, Lakshman MK. Pd-catalyzed C-C bond-forming reactions of thymidine mesitylene sulfonate. J Org Chem. 2007 Jul 20; 72(15):5724-30.
36. Champeil E, Pradhan P, Lakshman MK. Palladium-catalyzed synthesis of nucleoside adducts from bay- and fjord-region diol epoxides. J Org Chem. 2007 Jul 06; 72(14):5035-45.
37. Brulé C, Laali KK, Okazaki T, Lakshman MK. Structure/reactivity relationships in the benzo[c]phenanthrene skeleton: stable ion and electrophilic substitution (nitration, bromination) study of substituted analogues, novel carbocations and substituted derivatives. J Org Chem. 2007 Apr 27; 72(9):3232-41.
38. Bae S, Lakshman MK. O6-(benzotriazol-1-yl)inosine derivatives: easily synthesized, reactive nucleosides. J Am Chem Soc. 2007 Jan 31; 129(4):782-9.
39. Lakshman MK, Keeler JC, Ngassa FN, Hilmer JH, Pradhan P, Zajc B, Thomasson KA. Highly diastereoselective synthesis of nucleoside adducts from the carcinogenic benzo[a]pyrene diol epoxide and a computational analysis. J Am Chem Soc. 2007 Jan 10; 129(1):68-76.
40. Ngassa FN, Dekorver KA, Melistas TS, Yeh EA, Lakshman MK. Pd-Xantphos-catalyzed direct arylation of nucleosides. Org Lett. 2006 Sep 28; 8(20):4613-6.
41. Lagisetty P, Russon LM, Lakshman MK. A general synthesis of C6-azolyl purine nucleosides. Angew Chem Int Ed Engl. 2006 May 26; 45(22):3660-3.
42. Lakshman MK, Gunda P, Pradhan P. Mild and room temperature C-C bond forming reactions of nucleoside C-6 arylsulfonates. J Org Chem. 2005 Dec 09; 70(25):10329-35.
43. Pottabathini N, Bae S, Pradhan P, Hahn HG, Mah H, Lakshman MK. Synthesis and reactions of 2-chloro- and 2-tosyloxy-2'-deoxyinosine derivatives. J Org Chem. 2005 Sep 02; 70(18):7188-95.
44. Gunda P, Russon LM, Lakshman MK. Pd-catalyzed amination of nucleoside arylsulfonates to yield N6-aryl-2,6-diaminopurine nucleosides. Angew Chem Int Ed Engl. 2004 Nov 26; 43(46):6372-7.
45. Lakshman MK, Ngassa FN, Bae S, Buchanan DG, Hahn HG, Mah H. Synthesis of pyrene and benzo[a]pyrene adducts at the exocyclic amino groups of 2'-deoxyadenosine and 2'-deoxyguanosine by a palladium-mediated C-N bond-formation strategy. J Org Chem. 2003 Jul 25; 68(15):6020-30.
46. Okazaki T, Laali KK, Zajc B, Lakshman MK, Kumar S, Baird WM, Dashwood WM. Stable ion study of benzo[a]pyrene (BaP) derivatives: 7,8-dihydro-BaP, 9,10-dihydro-BaP and its 6-halo derivatives, 1- and 3-methoxy-9,10-dihydro-BaP-7(8H)-one, as well as the proximate carcinogen BaP 7,8-dihydrodiol and its dibenzoate, combined with a comparative DNA binding study of regioisomeric (1-, 4-, 2-) pyrenylcarbinols. Org Biomol Chem. 2003 May 07; 1(9):1509-16.
47. Zajc B, Grahek R, Kocijan A, Lakshman MK, Kosmrlj J, Lah J. Evaluation of the enantiomeric resolution of 7,8-dihydroxy-7,8-dihydrobenzo[a]-pyrene and its 6-fluoro and 6-bromo derivatives on polysaccharide-derived stationary phases. J Org Chem. 2003 Apr 18; 68(8):3291-4.
48. Lakshman MK, Gunda P. Palladium-catalyzed synthesis of carcinogenic polycyclic aromatic hydrocarbon epoxide-nucleoside adducts: the first amination of a chloro nucleoside. Org Lett. 2003 Jan 09; 5(1):39-42.
49. Lakshman MK, Thomson PF, Nuqui MA, Hilmer JH, Sevova N, Boggess B. Facile Pd-catalyzed cross-coupling of 2'-deoxyguanosine O6-arylsulfonates with arylboronic acids. Org Lett. 2002 May 02; 4(9):1479-82.
50. Lakshman MK, Hilmer JH, Martin JQ, Keeler JC, Dinh YQ, Ngassa FN, Russon LM. Palladium catalysis for the synthesis of hydrophobic C-6 and C-2 aryl 2'-deoxynucleosides. Comparison of C-C versus C-N bond formation as well as C-6 versus C-2 reactivity. J Am Chem Soc. 2001 Aug 15; 123(32):7779-87.
51. Page JE, Zajc B, Oh-hara T, Lakshman MK, Sayer JM, Jerina DM, Dipple A. Sequence context profoundly influences the mutagenic potency of trans-opened benzo[a]pyrene 7,8-diol 9,10-epoxide-purine nucleoside adducts in site-specific mutation studies. Biochemistry. 1998 Jun 23; 37(25):9127-37.
52. Chaturvedi S, Lakshman MK. Site-specific modification of the human N-ras proto-oncogene with each diol epoxide metabolite of benzo[a]pyrene and thermal denaturation studies of the adducted duplexes. Carcinogenesis. 1996 Dec; 17(12):2747-52.
53. Yeh HJ, Sayer JM, Liu X, Altieri AS, Byrd RA, Lakshman MK, Yagi H, Schurter EJ, Gorenstein DG, Jerina DM. NMR solution structure of a nonanucleotide duplex with a dG mismatch opposite a 10S adduct derived from trans addition of a deoxyadenosine N6-amino group to (+)-(7R,8S,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene: an unusual syn glycosidic torsion angle at the modified dA. Biochemistry. 1995 Oct 17; 34(41):13570-81.
54. LeBreton PR, Huang CR, Fernando H, Zajc B, Lakshman MK, Sayer JM, Jerina DM. Multiple fluorescence lifetimes for oligonucleotides containing single, site-specific modifications at guanine and adenine corresponding to trans addition of exocyclic amino groups to (+)-(7R,8S,9S,10R)- and (+)-(7S,8R,9R,10S) -7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene. Chem Res Toxicol. 1995 Apr-May; 8(3):338-48.
55. Schurter EJ, Yeh HJ, Sayer JM, Lakshman MK, Yagi H, Jerina DM, Gorenstein DG. NMR solution structure of a nonanucleotide duplex with a dG mismatch opposite a 10R adduct derived from trans addition of a deoxyadenosine N6-amino group to (-)-(7S,8R,9R,10S)-7,8-dihydroxy-9,10-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene. Biochemistry. 1995 Jan 31; 34(4):1364-75.
56. Christner DF, Lakshman MK, Sayer JM, Jerina DM, Dipple A. Primer extension by various polymerases using oligonucleotide templates containing stereoisomeric benzo[a]pyrene-deoxyadenosine adducts. Biochemistry. 1994 Nov 29; 33(47):14297-305.

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Purine Nucleosides
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