Phosphates of riboflavin and riboflavin analogs: A reinvestigation by high-performance liquid chromatography |
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Authors: | Peter Nielsen Peter Rauschenbach Adelbert Bacher |
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Institution: | 1. Laboratoire de Chimie Organique Structurale, ERA 557, Université Pierre et Marie Curie, 4 Place Jussieu, 75230 Paris Cedex 05, France;2. Laboratoire de Chimie Organique Biologique, ERA 823, Université Pierre et Marie Curie, 4 Place Jussieu, 75230 Paris Cedex 05, France |
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Abstract: | Phosphoric acid esters of riboflavin can be easily separated by reverse-phase high-performance liquid chromatography using eluants of 0.1 M ammonium formate in aqueous methanol. Commercial FMN preparations contained seven different flavin phosphates; the content of riboflavin 5'-phosphate was 70-75% and is in agreement with previous studies. Millimole amounts of crude FMN can be processed by preparative HPLC. The method permits the preparation of greater than 99%-pure 5'-FMN. The following compounds were isolated in pure form and their structures determined: riboflavin 4'-phosphate, riboflavin 3'-phosphate, riboflavin 4',5'-diphosphate; riboflavin 3',4'-diphosphate, and riboflavin 3',5'-diphosphate. The latter compound binds tightly to apoflavodoxin from Megasphaera elsdenii (KD = 9.7 X 10(-9) M). The bound flavin has high catalytic activity, thus representing a novel type of FMN analog. A wide variety of structural analogs of FMN can be obtained in pure form by preparative HPLC. |
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Keywords: | FMN FMN analogs riboflavin monophosphates riboflavin diphosphates high-performance liquid chromatography |
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