Journal of Chinese Pharmaceutical Sciences ›› 2015, Vol. 24 ›› Issue (6): 347-355.DOI: 10.5246/jcps.2015.06.045

• Original articles •     Next Articles

Efficient and convenient total synthesis of mycothiol on a large scale

Zijie Liu1, Youzhen Wu2, Gang Liu1,2*   

  1. 1. Beijing Key Laboratory of Active Substance Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
    2. Tsinghua-Peking Center for Life Sciences and Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084, China
  • Received:2015-04-20 Revised:2015-05-03 Online:2015-06-26 Published:2015-05-08
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  • Supported by:
    National Natural Science Foundation of China (NSFC, Grant No. 91213303).


Mycothiol (MSH) is the major low molecular weight thiol in most actinomycetes. Chemical synthesis of MSH is of value for enzymology and inhibitor screening assays, but is hampered by difficulties in large scale sysnthesis. We achieved the totalsynthesis of MSH by linking 2-camphanoyl-3,4,5,6-tetra-O-benzyl-D-myo-inositol (D-1) and 2-deoxy-2-azido-3,4,6-tri-O-benzyl-1-p-toluene-thio-D-glucoside (2) first, followed by coupling with N-Boc-S-acetyl-L-cysteine (3). This route of synthesis allowed the efficient and convenient synthesis of mycothiol on a large scale.

Key words: Mycothiol, Total synthesis, Large scale synthesis, Glycosylation

CLC Number: