Mycothiol(MSH)是放线菌体内普遍存在的一种重要的低分子量硫醇。因此,对其进行化学合成供酶学以及抑制剂筛选所需越显重要,但其化学合成路线供放大合成的发展一直面临一些屏障。我们在文献调研的基础上,通过整合目前最便捷、高效构建糖基供体、糖基受体以及半胱氨酸侧链三个片段的策略以及二糖与侧链的连接方法,发展了一种便捷、高效、可实现放大合成MSH的全合成策略。
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 total synthesis of MSH by linking 2-camphanoyl-3,4,5,6-tetra-O-benzyl-D-rnyo-inositol (D-1) and 2-deoxy-2-azido-3,4,6-tri-O-benzyl- 1-p-toluene-thio-o-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.