Research

Synthesis of S-Malic acid and S-Chlorosuccinic acid

 2017.10.18.

The researchers in chemistry faculty of Kim Il Sung University have synthesized directly S-malic acid and S-chlorosuccinic acid from S-aspartic acid which can be obtained by fermentation.

S-malic acid and S-chlorosuccinic acid, chiral succinic acid derivatives are being widely used as raw materials for drug synthesis. S-malic acid and S-chlorosuccinic acid are essential raw materials for the synthesis of L-carnitine, paclitaxel(Taxol) and other physiological activators. And they have been proved to be very useful for food additives and pH controllers of amino acid medicines and resolution substances of chiral molecules and so on.

Therefore, the synthesis of S-malic acid and S-chlorosuccinic acid and their applications are being widely studied.

Many previous researchers had first synthesized their racemic mixtures by addition reaction of H2O or hydrogen chloride to fumaric acid or malleic acid and then they had turned to their diastereoisomers using the pure chiral substances and then they had resoluted to obtain S-malic acid or S-chlorosuccinic acid.

In chemistry faculty of Kim Il Sung university the synthesis of S-malic acid and S-chlorosuccinic acid have been studied by a single reaction step; S-malic acid has been synthesized by reaction of S-aspratic acid with sodium nitrite and concentrated sulfuric acid; S-chlorosuccinic acid has been synthesized by reaction of S-aspratic acid with sodium nitrite and hydrochloric acid(37%) and sodium chloride.

We measured their melting points, optical rotations, IR spectrums for the identifi-cation of their structures and their purities were determined by using Ultrahigh-speed liquid chromatography(UPLC), respectively.

In future, we are going to study synthetic methods of physiological regulation substances like L-carnitine from S-maleic acid and S-chlorosuccinic acid.