/ Evans, David A.; Olhava, Edward J.

The solid-phase synthesis of trisubstituted thiazoles is described. The synthetic strategy involves the formation of a ­polymer-bound thiazole by reacting resin-bound cyanodithioimidocarbonic acid and α-bromoketone. The resin-bound thiazole was reacted with acyl chlorides or isocyanates. After oxidation-activation of a thioether linker to a sulfone linker, traceless cleavage was achieved with nucleophiles to give trisubstituted thiazoles.

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N5,N10 -methylene-THF + CO2 + NH4+ --> glycine (enzyme: glycine synthase; requires NADH)


JO - Journal of the American Chemical Society

T2 - Journal of the American Chemical Society

We can "walk through" this regulatory cascade by looking at aspecific example, namely increased levels of -ketoglutarate( reflecting a corresponding increase in NH3) levels:


JF - Journal of the American Chemical Society

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(1) Uridylyltransferase activity is increased

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(2) PII (in complex with adenylyltransferase)is uridylylated

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(3) Glutamine synthetase is deadenylylated

AB - The tri-alcohol-functionalised trithioether macrocycle 1,5,9-trithiacyclododecane-3,7,11-triol (HO)(3)[12]aneS(3), and its tri-anisate derivative have been synthesised, representing the first example of a thioether macrocycle functionalised on each backbone.

(4) -ketoglutarate and NH3 form glutamine and Pi

N2 - The tri-alcohol-functionalised trithioether macrocycle 1,5,9-trithiacyclododecane-3,7,11-triol (HO)(3)[12]aneS(3), and its tri-anisate derivative have been synthesised, representing the first example of a thioether macrocycle functionalised on each backbone.

Proline, Ornithine and Arginine are derived from Glutamate

AB - A series of molecules bearing multiple functional groups were synthesized to study their antibiotic effect against Gram-positive and Gram-negative bacteria and lipoxygenase activity as well. 2,4-Dimethylcarbolic acid (1) was refluxed with ethyl 2-bromoacetate to synthesize ethyl 2-(2,4-dimethylphenoxy)acetate (2). Compound 2 was converted to the corresponding hydrazide 3, again on refluxing with hydrazine. The compound 5-((2,4-dimethylphenoxy)methyl)-1,3,4-oxadiazol-2-thiol (4) was synthesized by the reaction of 3 and CS2 in the presence of KOH. Compound 4 was further converted to the corresponding ester 5 and then 2-(5-((2,4-dimethylphenoxy)methyl)-1,3,4-oxadiazol-2-ylthio)acetohydrazide (6). The final molecules N’-substituted-2-(5-((2,4-dimethylphenoxy)methyl)-1,3,4-oxadiazol-2-ylthio)acetohydrazide, 8a-m, bearing ether, 1,3,4-oxadiazole, thioether, hydrazone and azomethine functional groups were synthesized by stirring the aryl carboxaldehydes 7a-m with 6 in methanol at room temperature. The depicted structures of all synthesized molecules were corroborated by IR, 1H-NMR and EIMS spectral data analysis. 8m and 8i showed substantial antibacterial activity and lipoxygenase inhibitory activity, respectively.