One-step synthesis of N-acetylcysteine and glutathione derivatives using the Ugi reaction |
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Authors: | Alexander G Zhdanko |
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Institution: | Chemistry Department, Moscow State University, Leninskije Gory, 119991 Moscow, Russia |
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Abstract: | Fully protected natural and unnatural N-acetylcysteine, dipeptide Cys-Gly, glutathione, and homoglutathione derivatives were synthesized by the Ugi four-component reaction using various benzylthio aldehydes and ketones as carbonyl building blocks. The scope and limitations of the method were investigated. Formation of imidazoline by-products in the Ugi reaction was discussed. 2,2,2-Trifluoroethanol was shown to be a superior reaction media than methanol in some reactions. Also, the 4-methyl-2,6,7-trioxabicyclo2.2.2]octyl derivative (OBO-ester) of isocyanoacetic acid was shown to be superior to use than ethyl isocyanoacetate as a peptide synthesis precursor in cases when higher reactivity of an isocyanide is required. |
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Keywords: | Ugi reaction Cysteine Glutathione Homoglutathione Imidazoline Peptide chemistry |
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