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Medicinal-Pharmaceutical Chemistry Commons

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Full-Text Articles in Medicinal-Pharmaceutical Chemistry

Α-Vinyllysine And Α-Vinylarginine Are Time-Dependent Inhibitors Of Their Cognate Decarboxylases, David B. Berkowitz, Wan Jin Jahng, Michelle L. Pedersen Sep 1996

Α-Vinyllysine And Α-Vinylarginine Are Time-Dependent Inhibitors Of Their Cognate Decarboxylases, David B. Berkowitz, Wan Jin Jahng, Michelle L. Pedersen

Faculty Publications -- Chemistry Department

(±)-α-Vinyllysine and (±)-α-vinylarginine display time-dependent inhibition of L-lysine decarboxylase from B. cadaveris, and L-arginine decarboxylase from E. coli, respectively. A complete Kitz-Wilson analysis has been performed using a modification of the Palcic continuous UV assay for decarboxylase activity.


Synthesis Of Higher Α-Chlorovinyl And Α-Bromovinyl Amino Acids: The Amino Protecting Group Determines The Reaction Course, David B. Berkowitz, Michelle L. Pedersen, Wan Jin Jahng Jun 1996

Synthesis Of Higher Α-Chlorovinyl And Α-Bromovinyl Amino Acids: The Amino Protecting Group Determines The Reaction Course, David B. Berkowitz, Michelle L. Pedersen, Wan Jin Jahng

Faculty Publications -- Chemistry Department

N-Trifluoroacetyl α-vinyl amino esters are smoothly converted to the corresponding α-chlorovinyl or α-bromovinyl amino esters through the agency of phenyselenyl chloride or phenylselenyl bromide, respectively, followed by oxidation and pyrolysis. Exclusively the (E)-extemal halovinyl isomer and the internal halovinyl isomer are observed. The amino protecting group is a critical determinant of the reaction course (alkene addition vs. 5-exo-trig-like cyclization).


Synthesis Of Diterpene Alkaloids , Tiberiu Mircea Siclovan Jan 1996

Synthesis Of Diterpene Alkaloids , Tiberiu Mircea Siclovan

Retrospective Theses and Dissertations

Aconitine, atisine and garrya type diterpene alkaloids show remarkable biological activity and have a number of structural features in common. Due to their complex structure, there is a discrepancy between progress made lately in the identification, isolation and characterization of new members of this family, on one hand, and successful efforts towards their total synthesis, on the other;Our synthetic studies led us to develop a highly reproducible synthesis of adamantane-containing compounds via the corresponding bridgehead anions;Studies on the application of functionalized bridgehead radicals in natural product synthesis resulted in the development of a versatile, mild and highly tolerant ...


Total Synthesis Of Angularly Fused Natural Products , Guohua Zhao Jan 1996

Total Synthesis Of Angularly Fused Natural Products , Guohua Zhao

Retrospective Theses and Dissertations

The synthesis of angularly fused quinone natural product G-2N has been achieved using a photoenolization reaction and a Diels-Alder reaction in the key carbon-carbon bond forming steps. This route is direct and flexible. It should be applicable to synthesis of other analogous natural products;The skeleton of colchicine has been achieved using a Diels-Alder reaction followed by an electrophilic addition to the A ring as key steps. Our synthetic approach is direct. It could provide an efficient entry to total synthesis of colchicine.