Grant R. Krow
B.A. (1963), Albright College
J.D. (1978) Temple University
Synthetic and Mechanistic Organic Chemistry
Small Bridged-Ring Nitrogen Heterocycles. Synthetic methods are under development to prepare methanopyrrolidines (2-azabicyclo[2.1.1]hexanes) 1 with heteroatom, alkyl, aryl, or acyl functionality at the various ring positions C 1 -C 6 . Our major current efforts are directed toward discovery of efficient photochemical or rearrangement routes that will allow for stereocontrol and regiocontrol in the introduction of substituents.
Bioactive Molecule Synthesis. We are applying insights obtained from the preparation of methanopyrrolidines 1 to the generation of monomer pools for incorporation into ß-peptide tertiary amide foldamers 2 . Other projects involve synthesis of conformationally constrained analogs of heteroatom-functionalized methanoprolines 3 in the search for more stable forms of collagen.
Krow, Grant R.; Edupuganti, Ram; Gandla, Deepa; "5(6)-anti-Substituted-2-azabicyclo[2.2.1]hexanes." Journal of Organic Chemistry. (2009), 74, 21, 8232-8242
Choudhary, A.; Gandla, D.: Krow, GR: "Nature of Amide Carbonyl-Carbonyl Interactions in Proteins." Journal of American Chemical Society. (2009), 131, 21, 7244
K.L. Gorres, R. Edupuganti, G.R. Krow, "Conformational preferences of substances for human prolyl 4-hydroxylase." Biochemistry. (2008) , 47, 36, 9447-9455.
G.R. Krow, P.E. Sonnet, "Carbamate-stabilized anions of 2-azabicyclo[2.1.1]hexanes." Tetrahedron. (2008) , 64, 30-31, 7131-7135.
G.R. Krow, D. Gandla, W.W. Guo, "Neighboring group participation in the additions of iodonium and bromonium ions to N-alkoxycarbonyl-2-azabicyclo[2.2.n]alk-5-enes (n=1,2)." Journal of Organic Chemistry. (2008) , 73, 6, 2114-2121.
G.R. Krow, D. Gandla, W.W. Guo, "Selectfluor as a nucleofuge in the reactions of azabicyclo[n.2.1]alkane beta-halocarbamic acid esters (n=2,3)." Journal of Organic Chemistry. (2008) , 73, 6, 2122-2129.