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Barbara Zajc

TitleInvestigator
Faculty RankProfessor
InstitutionCity College, CUNY
Departmentchemistry
AddressThe City College of New York
Department of Chemistry
160 Convent Avenue
New York NY 10031
Phone212-650-8926
Fax212-650-6107
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    Collapse Biography 
    Collapse awards and honors
    1991 - 1994Fogarty Fellowship, National Institutes of Health
    2012Recognition as Outstanding Mentor, The City University of New York

    Collapse Overview 
    Collapse overview
    Background

    Prof. Zajc obtained the PhD degree from the University of Ljubljana, Slovenia, and did postdoctoral work as a Fogarty Fellow at the National Institutes of Health, Bethesda. She moved from University of Ljubljana, where she was a tenured faculty member, to The City College of New York, where she is currently Professor of Chemistry with tenure.

    Research

    Our research is in the area of organofluorine chemistry, with the focus on development of novel regiospecific fluorination methods, and the use of fluorine as a probe in studies related to metabolism and biological activity of environmental pollutants. The importance for this area of research is exemplified in the fact that over 150 commercial pharmaceuticals contain fluorine atom.

    In the area of methods development, novel fluorinated building blocks are synthesized and their reactivities are studied. These building blocks are then used for polyfunctionalization, via a modular synthesis approach. Specifically, we are developing a series of fluorinated Julia-Kocienski reagents, where fluorine atom is introduced via metalation-electrophilic fluorination. To gain a deeper understanding of the chemical methodology, reactivities of these reagents are studied in olefination reactions, and also compared with unfluorinated analogs. The overall goal of our work is the development of a “chemical fluoroolefination toolbox” for the synthesis of diverse functionalized fluorinated alkenes. We are also involved with the development of biologically important compounds, such as potential anti-tumor and antiviral agents, via our fluorination chemistry approaches.

    In the studies related to the influence of environmental pollutants on human health, we are utilizing fluorine atom to modulate biological activity. In this area, our research involves synthesis of fluorinated analogs of environmental pollutants, their putative metabolites and DNA conjugates, for structure activity studies. This often entails the development of stereoselective methodologies, evaluation of chirality in products, and multistep syntheses.

    Collapse Bibliographic 
    Collapse selected publications
    Publications listed below are automatically derived from MEDLINE/PubMed and other sources, which might result in incorrect or missing publications. Faculty can login to make corrections and additions.
    Newest   |   Oldest   |   Most Cited   |   Most Discussed   |   Timeline   |   Field Summary   |   Plain Text
    PMC Citations indicate the number of times the publication was cited by articles in PubMed Central, and the Altmetric score represents citations in news articles and social media. (Note that publications are often cited in additional ways that are not shown here.) Fields are based on how the National Library of Medicine (NLM) classifies the publication's journal and might not represent the specific topic of the publication. Translation tags are based on the publication type and the MeSH terms NLM assigns to the publication. Some publications (especially newer ones and publications not in PubMed) might not yet be assigned Field or Translation tags.) Click a Field or Translation tag to filter the publications.
    1. Akula HK, Bae S, Pradhan P, Yang L, Zajc B, Lakshman MK. Diversely C8-functionalized adenine nucleosides via their underexplored carboxaldehydes. Chem Commun (Camb). 2022 Feb 03; 58(11):1744-1747. PMID: 35029254.
      Citations:    Fields:    
    2. Wei W, Khangarot RK, Stahl L, Veresmortean C, Pradhan P, Yang L, Zajc B. Correction to Generating Stereodiversity: Diastereoselective Fluorination and Highly Diastereoselective Epimerization of a-Amino Acid Building Blocks. Org Lett. 2021 Jun 04; 23(11):4508. PMID: 34029105.
      Citations:    Fields:    
    3. Korvinson KA, Akula HK, Malinchak CT, Sebastian D, Wei W, Khandaker TA, Andrzejewska MR, Zajc B, Lakshman MK. Catalytic Reductions Without External Hydrogen Gas: Broad Scope Hydrogenations with Tetrahydroxydiboron and a Tertiary Amine. Adv Synth Catal. 2020 Jan 07; 362(1):166-176. PMID: 33071705.
      Citations:    
    4. Wei W, Khangarot RK, Stahl L, Veresmortean C, Pradhan P, Yang L, Zajc B. Generating Stereodiversity: Diastereoselective Fluorination and Highly Diastereoselective Epimerization of a-Amino Acid Building Blocks. Org Lett. 2018 06 15; 20(12):3574-3578. PMID: 29856640.
      Citations: 3     Fields:    Translation:Cells
    5. Lakshman MK, Zajc B. When nucleoside chemistry met hypervalent iodine reagents. ARKIVOC. 2018; 2018(Pt II):252-279. PMID: 30221252.
      Citations:    
    6. Lakshman MK, Tine FA, Khandaker TA, Basava V, Agyemang NB, Benavidez MSA, Ga?i 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. PMID: 28713205.
      Citations:    
    7. Banerjee S, Sinha S, Pradhan P, Caruso A, Liebowitz D, Parrish D, Rossi M, Zajc B. Regiospecifically Fluorinated Polycyclic Aromatic Hydrocarbons via Julia-Kocienski Olefination and Oxidative Photocyclization. Effect of Fluorine Atom Substitution on Molecular Shape. J Org Chem. 2016 05 20; 81(10):3983-93. PMID: 27009471.
      Citations: 3     Fields:    Translation:Cells
    8. Kumar R, Singh G, Todaro LJ, Yang L, Zajc B. E- or Z-Selective synthesis of 4-fluorovinyl-1,2,3-triazoles with fluorinated second-generation Julia-Kocienski reagents. Org Biomol Chem. 2015 Feb 07; 13(5):1536-49. PMID: 25491086.
      Citations: 4     Fields:    Translation:Cells
    9. Chowdhury M, Mandal SK, Banerjee S, Zajc B. Synthesis of regiospecifically fluorinated conjugated dienamides. Molecules. 2014 Apr 10; 19(4):4418-32. PMID: 24727415.
      Citations: 2     Fields:    Translation:Cells
    10. Ayeni DO, Mandal SK, Zajc B. Julia-Kocienski Approach to Trifluoromethyl-Substituted Alkenes1. Tetrahedron Lett. 2013 Nov 06; 54(45):6008-6011. PMID: 25568501.
      Citations:    Fields:    
    11. Singh G, Kumar R, Swett J, Zajc B. Modular synthesis of N-vinyl benzotriazoles. Org Lett. 2013 Aug 16; 15(16):4086-9. PMID: 23915255.
      Citations: 3     Fields:    Translation:Cells
    12. Kumar R, Zajc B. Stereoselective synthesis of conjugated fluoro enynes. J Org Chem. 2012 Oct 05; 77(19):8417-27. PMID: 23005035.
      Citations: 6     Fields:    Translation:Cells
    13. Mandal SK, Ghosh AK, Kumar R, Zajc B. Expedient synthesis of a-substituted fluoroethenes. Org Biomol Chem. 2012 Apr 28; 10(16):3164-7. PMID: 22349519.
      Citations: 6     Fields:    Translation:Cells
    14. Kumar R, Pradhan P, Zajc B. Facile synthesis of 4-vinyl- and 4-fluorovinyl-1,2,3-triazoles via bifunctional "click-olefination" reagents. Chem Commun (Camb). 2011 Apr 07; 47(13):3891-3. PMID: 21336351.
      Citations: 6     Fields:    Translation:Cells
    15. Zajc B, Kumar R. Synthesis of Fluoroolefins via Julia-Kocienski Olefination. Synthesis (Stuttg). 2010; 2010(11):1822-1836. PMID: 22544979.
      Citations:    
    16. Ghosh AK, Zajc B. Fluorinated 1-phenyl-1H-tetrazol-5-yl sulfone derivatives as general reagents for fluoroalkylidene synthesis. J Org Chem. 2009 Nov 20; 74(22):8531-40. PMID: 19831343.
      Citations: 4     Fields:    Translation:Cells
    17. Ghosh AK, Banerjee S, Sinha S, Kang SB, Zajc B. Alpha-fluorovinyl Weinreb amides and alpha-fluoroenones from a common fluorinated building block. J Org Chem. 2009 May 15; 74(10):3689-97. PMID: 19361189.
      Citations: 9     Fields:    Translation:Cells
    18. del Solar M, Ghosh AK, Zajc B. Fluoro-Julia olefination as a mild, high-yielding route to alpha-fluoro acrylonitriles. J Org Chem. 2008 Nov 07; 73(21):8206-11. PMID: 18841918.
      Citations: 6     Fields:    
    19. He M, Ghosh AK, Zajc B. Julia Olefination as a General Route to Phenyl (alpha-Fluoro)vinyl Sulfones. Synlett. 2008 Apr 01; 2008(7):999-1004. PMID: 19888442.
      Citations:    
    20. Ghosh AK, Lagisetty P, Zajc B. Direct synthesis of 8-fluoro purine nucleosides via metalation-fluorination. J Org Chem. 2007 Oct 26; 72(22):8222-6. PMID: 17902691.
      Citations: 6     Fields:    Translation:Cells
    21. 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. PMID: 17764198.
      Citations: 5     Fields:    Translation:HumansCells
    22. 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. PMID: 17199284.
      Citations: 3     Fields:    
    23. Zajc B, Kake S. Exceptionally mild, high-yield synthesis of alpha-fluoro acrylates. Org Lett. 2006 Sep 28; 8(20):4457-60. PMID: 16986924.
      Citations: 14     Fields:    
    24. Ghosh AK, Zajc B. High-yield synthesis of fluorinated benzothiazolyl sulfones: general synthons for fluoro-julia olefinations. Org Lett. 2006 Apr 13; 8(8):1553-6. PMID: 16597108.
      Citations: 12     Fields:    Translation:Cells
    25. 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. PMID: 12926280.
      Citations: 1     Fields:    Translation:HumansAnimalsCells
    26. 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. PMID: 12688804.
      Citations:    Fields:    Translation:Cells
    27. Kramata P, Zajc B, Sayer JM, Jerina DM, Wei CS. A single site-specific trans-opened 7,8,9,10-tetrahydrobenzo[a]pyrene 7,8-diol 9,10-epoxide N2-deoxyguanosine adduct induces mutations at multiple sites in DNA. J Biol Chem. 2003 Apr 25; 278(17):14940-8. PMID: 12595542.
      Citations: 5     Fields:    Translation:AnimalsCells
    28. Simhadri S, Kramata P, Zajc B, Sayer JM, Jerina DM, Hinkle DC, Wei CS. Benzo[a]pyrene diol epoxide-deoxyguanosine adducts are accurately bypassed by yeast DNA polymerase zeta in vitro. Mutat Res. 2002 Oct 31; 508(1-2):137-45. PMID: 12379469.
      Citations: 7     Fields:    Translation:Animals
    29. Zajc B. Synthesis of (+/-)-trans-7,8-Dihydrodiol of 6-Fluoro-benzo[a]pyrene via Hydroxyl-Directed Regioselective Functionalization of Substituted Pyrene. J Org Chem. 1999 Mar 19; 64(6):1902-1907. PMID: 11674280.
      Citations: 3     Fields:    
    30. Custer L, Zajc B, Sayer JM, Cullinane C, Phillips DR, Cheh AM, Jerina DM, Bohr VA, Mazur SJ. Stereospecific differences in repair by human cell extracts of synthesized oligonucleotides containing trans-opened 7,8,9, 10-tetrahydrobenzo[a]pyrene 7,8-diol 9,10-epoxide N2-dG adduct stereoisomers located within the human K-ras codon 12 sequence. Biochemistry. 1999 Jan 12; 38(2):569-81. PMID: 9888796.
      Citations: 2     Fields:    Translation:HumansCells
    31. Lipinski LJ, Ross HL, Zajc B, Sayer JM, Jerina DM, Dipple A. Effect of single benzo[a]pyrene diol epoxide-deoxyguanosine adducts on the action of DNA polymerases in vitro. Int J Oncol. 1998 Aug; 13(2):269-73. PMID: 9664121.
      Citations: 7     Fields:    Translation:Cells
    32. 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. PMID: 9636059.
      Citations: 17     Fields:    Translation:Cells
    33. 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. PMID: 7578919.
      Citations: 1     Fields:    Translation:AnimalsCells
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