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化学学报
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化学学报 ›› 2002, Vol. 60 ›› Issue (2): 343-346. 上一篇    下一篇

研究论文

4-氨基-L-赤-生物蝶呤的全合成研究

姚其正;张志祥;肖莉   

  1. 中国药学院
  • 发布日期:2002-02-15

Study on the total synthesis of 4-amino-L-erythro-biopterin

Yao Qizheng;Zhang Zhixiang;Xiao Li   

  • Published:2002-02-15

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报道了两种合成4-氨基-L-赤-生物蝶呤(2)的方法：(1)以2-N-1',2'-O-三乙酰基-L-赤-生物蝶呤(3)为原料，经4-O-甲基化、氨解而得2；(2)为4-氨基-L-赤-生物蝶呤(2)的“一锅法”全合成，即通过保护了的5-脱氧-L-阿拉伯糖(9)和2,4,5,6,-四氨基嘧啶缩合，经碘氧化得到二乙酰氨基生物蝶呤(11)，11的进一步乙酰化后即可经硅胶柱层析纯化，获得四乙酰基氨基生物蝶呤(12)，用NH3-H2O/MeOH皂化12即得2。5-脱氧-L-阿拉伯糖(7)由L-鼠李糖二乙基缩硫醛衍生物(5)制得，这样由5制备2的总收率为17%。

关键词: 生物蝶呤, 抑制剂, 蝶呤, 一氧化氮, 合成酶, 全合成

A total synthesis of 4-amino-L-erythro-biopterin(2) in a one-pot process is described, which comprises the following main steps: (a) oxidation of L-rhamnose diethylmercaptal (5) with H2O2/HCOOH to its bis-sulfone(6), (b) preparation of 5-deoxy-L-arabinose (7) through aminolysis of 6, (c) condensation of the protected 5-deoxy-L- arabinose (9) with tetraaminopyrimidine, (d) iodine oxidation of the formed tetrahydroaminobiopterin derivative (10) to 1', 2'-O-diacetyl- L-erythro-aminobiopterin (12) and purification of 12 using column chromatography, and (f) deacetylation of 12 with NH3-H2O/MeOH to give 2. Thus, the overall yield of 2 from 5 was 17%.

Key words: INHIBITOR, PTERIN, NITROGEN MONOXIDE, SYNTHETASE, TOTAL SYNTHESIS

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