Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (9): 1073-1078.DOI: 10.11944/j.issn.1000-0518.2016.09.150444

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Chemoenzymatic Synthesis of Danshensu

YANG Lingying,ZENG Qingyou(),YANG Daomao   

  1. School of Chemical Engineering,Huaqiao University,Xiamen,Fujian 361021,China
  • Received:2015-12-14 Accepted:2016-04-01 Published:2016-08-23 Online:2016-08-23
  • Contact: ZENG Qingyou
  • Supported by:
    Supported by Fundamental Research Funds for the Central Universities(No.JB-ZR1153)

Abstract:

Danshensu is one of water-soluble components in Chinese medicine Danshen(Salvia miltiorrhiza bunge) and has some potential pharmaceutical activities. Danshensu was prepared through chemoenzymatic synthesis starting from the Erlenmeyer condensation of 3,4-dihydroxybenzaldehyde and acetyl glycine and followed by ring opening reaction to give α-acetamino-β-(3,4-diacetoxylphenyl)acrylic acid. Hydrolysis of the substituted acrylic acid with hydrochloric acid gave β-(3,4-dihydroxyphenyl) pyruvate. Finally, Danshensu was obtained by enzymatic reduction of β-(3,4-dihydroxyphenyl) pyruvate with resting cells of pediococcus acidilactici. The overall yield is 69.4% and the optical purity of Danshensu is 97.5% ee.

Key words: resting cells of pediococcus acidilactici, chemoenzymatic synthesis, Danshensu