First total synthesis of mycothiol and mycothiol disulfide
First total synthesis of mycothiol and mycothiol disulfide
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DOI：
10.1021/ol0362008
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发表时间：
2004-02-05
期刊：
影响因子：
5.2
通讯作者：
Rosazza, JPN
中科院分区：
文献类型：
--
作者：
Lee, S;Rosazza, JPN
以D-2，3，4，5，6-五O-乙酰肌醇、O-(3，4，6-三O-乙酰基)-2-叠氮-2-脱氧-α，β-D-吡喃葡萄糖基三氯乙酰亚氨酸酯和N，S-二乙酰基-L-半胱氨酸为原料，脱保护过乙酰化的肌醇，首次全合成了霉硫醇和霉硫醇二硫化物。首次报道了未衍生化真菌硫醇的全光谱表征。通过对已知的双胺类化合物进行光谱分析，确定了霉硫醇的结构。
The first total synthesis of mycothiol and mycothiol disulfide was achieved by linking D-2,3,4,5,6-penta-O-acetyl-myo-inositol, O-(3,4,6-tri-O-acetyl)-2-azido-2-deoxy-alpha,beta-D-glucopyranosyl) trichloroacetimidate, and N,S-diacetyl-L-cysteine and deprotecting peracetylated mycothiol. The first full spectral characterization is reported for underivatized mycothiol. The structure of mycothiol was confirmed by spectral analysis of the known bimane derivative.