Identification of the products of reaction between pyridoxal phosphate and amiclenomycin and other related 1-amino-cyclohexa-2,5-dienes |
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| Authors: | Sté phane MannDenis Lesage,Jean-Claude TabetAndré e Marquet |
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| Affiliation: | a Laboratoire de Chimie Organique Biologique, Université Paris VI, UMR CNRS 7613, 4, Place Jussieu, 75252 Paris cedex 05, France
b Laboratoire de Chimie Structurale Organique et Biologique, Université Paris VI, UMR CNRS 7613, 4, Place Jussieu, 75252 Paris cedex 05, France |
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| Abstract: | Amiclenomycin, a natural product containing the 1-amino cyclohexa-2,5-diene moiety is an inhibitor of 7;8-diaminopelargonic acid aminotransferase, a pyridoxal phosphate (PLP) dependent enzyme involved in biotin biosynthesis. The postulated mechanism implies the aromatisation of the Schiff base formed between PLP and amiclenomycin. Aromatic adducts have been obtained by heating PLP with amiclenomycin and other related 1-amino cyclohexa-2,5-dienes. They were fully characterized by UV-visible and ESI mass spectrometry and provide standards for identification of the enzyme-derived products. |
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| Keywords: | pyridoxal phosphate amiclenomycin 1-amino-cyclohexa-2,5-dienes syn 1,4-elimination ESI mass spectrometry |
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