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84870723193
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In reactions of aspartic acid and glutamic acid, the α-amino acid moieties participate in a Ugi 4-component 5-center reaction, while the carboxylate side chain participated in a Passerini reaction. This is a so-called tandem Ugi-Passerini reaction.
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In reactions of aspartic acid and glutamic acid, the α-amino acid moieties participate in a Ugi 4-component 5-center reaction, while the carboxylate side chain participated in a Passerini reaction. This is a so-called tandem Ugi-Passerini reaction.
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20
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84870723917
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Except for reactions with tryptophan, tyrosine and serine, our yields are higher than those reported by Ugi. In the aforementioned cases, Ugi included triethylamine presumably to enhance the nucleophilicity of methanol. These findings imply that these reactions need not be performed at -30°C.
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Except for reactions with tryptophan, tyrosine and serine, our yields are higher than those reported by Ugi. In the aforementioned cases, Ugi included triethylamine presumably to enhance the nucleophilicity of methanol. These findings imply that these reactions need not be performed at -30°C.
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84870667898
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Note
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Arginine's basic guanidinium group facilitates solvolytic cleavage of the isocyanide carbamate, yielding a methyl carbamate. The poor solubility of cysteine in methanol and acetonitrile precludes efficient reaction.
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84870694562
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Note
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Benzylamine, 4-pentenoic acid, and/or isobutyraldehyde were selected for use as the other U-4CR substrates in these derivatization experiments.
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33748921576
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