Department Faculty

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Bakthan Singaram
  • Title
    • Professor
  • Division Physical & Biological Sciences Division
  • Department
    • Chemistry & Biochemistry Department
  • Phone
    831-459-3154 (Office), 831-459-3479 (Lab)
  • Email
  • Website
  • Office Location
    • Physical Sciences Building, 348
    • Physical Sciences Bldg 348 (Office)
    • Physical Sciences Bldg 398 (Lab)
  • Mail Stop Chemistry
  • Faculty Areas of Expertise Chemistry

Summary of Expertise

Organic synthesis, organoborane chemistry, heterocyclic chemistry, organometallic chemistry, asymmetric synthesis, biosensors, and natural products chemistry

Research Interests

There are many optically active organic compounds of biological and medicinal significance. For example, statine analogs, antibiotics, anesthetics, ACE inhibitors, macrolides, heterocyclic compounds, unusual amino acids, and insect pheromones all contain stereogenic centers. There is, therefore, a continuous need for new asymmetric methodology. A major objective of Bakthan Singaram's research program is the development of asymmetric and/or enantioselective methods.

Within this context, an important aspect of his study is to develop novel and efficient chiral auxiliaries and catalysts derived from terpenes, organic acids, and other naturally occurring organic compounds. These compounds are tested for their efficiency in asymmetric reduction and asymmetric allylmetallation reactions. Current emphasis is centered in the areas of organometallics, heteroatom stabilized carbanions, and imine intermediates.

Another aspect of Dr. Singaram's research involves the development of an optical glucose sensor. Diabetes Mellitus continues to debilitate millions of people worldwide. Although there is no cure for the disease, there are effective ways to manage it. One of the most important ways, involves the monitoring of the blood-glucose levels. Currently, diabetics prick their finger and test the blood three to four times a day. Because glucose levels fluctuate drastically throughout the day, an accurate measure of blood-glucose is difficult. A continuous glucose monitor would thus be of great interest. Research in this area includes the utilization of organoboranes for the development of novel fluorescent chemosensors.

Biography, Education and Training

B.Sc., M.Sc., Ph.D., University of Madras, Tamil Nadu, India

Selected Publications

  • Murphy, Chris L.; Hall, Aaron; Roberts, Emily J.; Ryan, Matthew D.; Clary, Jacob W.; Singaram, Bakthan Preparation and reactions of 4-​iodobutyl pinacolborate. Synthesis of substituted alkyl and aryl pinacolboronates via 4-​iodobutyl pinacolborate utilizing tetrahydrofuran as the leaving group Tetrahedron Letters (2015), 56(23), 3032-3033.
  • Bailey, Christopher L.; Clary, Jacob W.; Tansakul, Chittreeya; Klabunde, Lucas; Anderson, Christopher L.; Joh, Alexander Y.; Lill, Alexander T.; Peer, Natalie; Braslau, Rebecca; Singaram, Bakthan Reduction of Weinreb amides to aldehydes under ambient conditions with magnesium borohydride reagents Tetrahedron Letters (2015), 56(5), 706-709.
  • Snelling, Rachel; Saavedra, Jaime Z.; Bayrasy, Panathda; Abdollahian, Yashar; Singaram, Bakthan Binary reducing agents containing dichloroindium hydride for the selective, partial, or tandem reductions of bifunctional compounds consisting of halo-​nitriles, halo-​esters and halo-​carboxylic acids Organic Chemistry Frontiers (2015), 2(2), 133-140.
  • Resendez, Angel; Abdul Halim, Md; Landhage, Caroline M.; Hellstrom, Per M.; Singaram, Bakthan; Webb, Dominic-Luc Rapid small intestinal permeability assay based on riboflavin and lactulose detected by bis-​boronic acid appended benzyl viologens Clinica Chimica Acta (2015), 439, 115-121.
  • Vilozny, Boaz; Wollenberg, Alexander L.; Actis, Paolo; Hwang, Daniel; Singaram, Bakthan; Pourmand, Nader Carbohydrate-​actuated nanofluidic diode: switchable current rectification in a nanopipette Nanoscale (2013), 5(19), 9214-9221.
  • Bailey, Christopher L.; Murphy, Chris L.; Clary, Jacob W.; Eagon, Scott; Gould, Naomi; Singaram, Bakthan Reaction of Grignard reagents with diisopropylaminoborane. Synthesis of alkyl, aryl, heteroaryl and allyl boronic acids from organo(diisopropyl)​aminoborane by a simple hydrolysis Heterocycles (2012), 86(1), 331-341.
  • Singaram, Bakthan. Sweetness and light: Continuous glucose sensing with a fluorescent thin-film hydrogel. Abstracts of Papers, 237th ACS National Meeting, Salt Lake City, UT, United States, March 22-26, 2009 (2009), CARB-032.
  • Binder, Caitlin M.; Bautista, April; Zaidlewicz, Marek; Krzeminski, Marek P.; Oliver, Allen; Singaram, Bakthan. Dual Stereoselectivity in the Dialkylzinc Reaction Using (-)-.beta.-Pinene Derived Amino Alcohol Chiral Auxiliaries. Journal of Organic Chemistry (2009), 74(6), 2337-2343.
  • Haddenham, Dustin; Pasumansky, Lubov; DeSoto, Jamie; Eagon, Scott; Singaram, Bakthan. Reductions of Aliphatic and Aromatic Nitriles to Primary Amines with Diisopropylaminoborane. Journal of Organic Chemistry (2009), 74(5), 1964-1970.
  • Eagon, Scott; Kim, Jinsoo; Singaram, Bakthan. Mild and practical reductions of prochiral ketones to chiral alcohols using the chiral boronic ester TarB-H. Synthesis (2008), (23), 3874-3876.
  • Kim, Jinsoo; Bruning, John; Park, Kevin E.; Singaram, Bakthan. Highly Regioselective and Enantioselective 1,2-Reductions of .alpha.,.beta.-Unsaturated Ketones Using TarB-NO2. Abstracts, 42nd Western Regional Meeting of the American Chemical Society, Las Vegas, NV, United States, September 23-27 (2008).
  • Schiller, Alexander; Vilozny, Boaz; Wessling, Ritchie A.; Singaram, Bakthan. Recognition of phospho sugars and nucleotides with an array of boronic acid appended bipyridinium salts. Analytica Chimica Acta (2008), 627(2), 203-211.
  • Binder, Caitlin M.; Dixon, Darryl D.; Almaraz, Erik; Tius, Marcus A.; Singaram, Bakthan. A simple procedure for C-C bond cleavage of aromatic and aliphatic epoxides with aqueous sodium periodate under ambient conditions. Tetrahedron Letters (2008), 49(17), 2764-2767.
  • Vilozny, Boaz; Schiller, Alexander; Yao, Fanny; Sharrett, Zachary; Wessling, Ritchie A.; Singaram, Bakthan. Fluorescent saccharide sensing at physiological pH with an ensemble of sulfonated water-soluble perylene-diimide and boronic acid-appended viologen. Abstracts of Papers, 235th ACS National Meeting, New Orleans, LA, United States, April 6-10, 2008 (2008), ORGN-259.
  • Schiller, Alexander; Wessling, Ritchie A.; Singaram, Bakthan. Recognition of carbohydrates and nucleotides with an array of boronic acid appended bipyridinium salts. Abstracts of Papers, 235th ACS National Meeting, New Orleans, LA, United States, April 6-10, 2008 (2008), ORGN-258.
  • Sharrett, Zachary; Gamsey, Soya; Levine, Paul; Cunningham-Bryant, Dan; Vilozny, Boaz; Schiller, Alexander; Wessling, Ritchie A.; Singaram, Bakthan. Boronic acid-appended bis-viologens as a new family of viologen quenchers for glucose sensing. Abstracts of Papers, 235th ACS National Meeting, New Orleans, LA, United States, April 6-10, 2008 (2008), ORGN-257.