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PubMed · 641800

Alanine derivatives with reactive groups.

B Paul·W Korytnyk
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Abstract

The synthesis of diazoketone analogs of amino acids and associated problems were investigated with N-phthaloyl-DL-alanine serving as a model. The carboxyl was activated by conversion to the acid chloride or, under mild conditions, to the mixed anhydride obtained with ethyl chloroformate or dicyclohexylcarbodiimide; the product was reacted with diazomethane. Deblocking the phthaloyl group with hydrazine gave 3-amino-1-diazo-2-butanone as a well-characterized solid salt and as a less stable oil. Further reactions of the blocked diazoketone of DL-alanine, such as conversion to alpha-haloketones, Wolff rearrangement, and deuterium exchange on C-1 were investigated. 3-A-mino-1-diazo-2-butanone had moderate inhibitory activity against mouse mammary adenocarcinoma in cell culture.

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AdenocarcinomaAlanineAnimalsAntimetabolites, AntineoplasticCells, CulturedMammary Neoplasms, ExperimentalMethodsMiceJournal ArticleResearch Support, U.S. Gov't, P.H.S.

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B Paul, W Korytnyk. 1978. Alanine derivatives with reactive groups.. https://doi.org/10.1002/jps.2600670518

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