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含四氢噻吩类生物素杂质的合成

Synthesis of d-biotin impurity with tetrahydrothiophen compound
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摘要 Three new impurities of d-Biotin were synthesized:(2S,3S,4S)-5-(3,4-diamino-tetrahydro-thiophen-2-yl)-pentanoic acid,(3aS,4S,6aR)-hexahydro-1-thia-3,4a-diaza-cyclopenta inden-4-one and(3aS,4S,6aR)-4-(5’-Oxo-hexyl)-tetrahydro-thieno-imidazol-2-one.Structures of target compounds were confirmed by NMR and so on.Our work further improved the research on the impurities of d-biotin,and can be applied to the quality control and quality assurance of d-biotin. Three new impurities of d-Biotin were synthesized： （ 2S, 3 S, 4S ） -5- （ 3,4 -diamino- tetrahydro -thiophen-2 -yl ） -pentanoie acid, （3aS,4S, 6aR） -hexahydro-1 -thia-3,4a-diaza-cyclopenta [ cd ] i nden-4-one and （3 aS,4S,6aR） -4- （5＇ -Oxo-hexyl ） -tetrahydro-thieno-[3,6] imidazol-2-one. Structures of target compounds were confirmed by NMR and so on. Our work further improved the research on the impurities of d-biotin, and can be applied to the quality control and quality assurance of d-biotin.
作者 陈建辉 潘一斌 陈浙蓉
机构地区 南京工业大学制药与生命科学学院 浙江医药股份有限公司新昌制药厂
出处 《化学研究与应用》 CAS CSCD 北大核心 2009年第3期416-418,共3页 Chemical Research and Application
基金 国家科技兴贸行动专项(2006GH553302)资助项目 浙江省重大科技专项(2006C11190)资助项目
关键词 生物素 有关物质 四氢噻吩 合成 d-biotin impurities tetrahydrothiophen synthesis
分类号 O626.12 [理学—有机化学]
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参考文献13

  • 1Mistry, P. S. ; Dakshinamurti, K. Biochemistry of biotin [ J ]. Vitam. Horm. , 1964,22,1-55.
  • 2CoggeshaU, C. J. ; Heggers,P. J. ; Robson,C. M. ; Baker, H. Biotin status and plasma glucose in diabetics [ J ]. Ann. NY Acad. Sci. , 1985,447,389-392.
  • 3Maebashi M, Makino Y, Furukawa Y, Ohinata K, Kimura S, Sato T. Therapeutic evaluation of the effect of biotin on hyperglycemia in patients with non-insulin dependent diabetes mellitus [ J ]. J. Clin. Biochem. Nutr. , 1993 ; 14 : 211-215.
  • 4McCormick, D. B. Biotin [ J ]. Nutr. Rev. ( 1975 ) 33 : 97-102
  • 5欧洲药典委员会.欧洲药典[S].EP5.0,2005:1073,1100.1101.
  • 6美国药典委员会,美国药典[S],USP28,2005:230.
  • 7Cheney, L. C. ; Piening,J. R. The total synthesis of 2,3,4,5-tetradedrobiotin [ J ] J. Am. Chem. Soc. , 1945, 67, 731-735.
  • 8Nishimura S. Imoto E. Studies on thiophene compounds.ⅪⅩ. syntheses of 2,3,4,5-tetradehydrobiotin and 2,3,4,5- tetradehydronorbiotin [J]. Bull. Chem. Soc. Jpn. , 1962,35, 432-7.
  • 9Hanka, L. J. , D. G. Martin, and L. M. Reineke. Two new antimetabolites of biotin: α-methyldethiobiotin and α-methylbiotin [ J ]. Antimicrob. Agents Chemother, 1972, 1:135-138.
  • 10Dixon R. W. , Radmer R. J. , Kuhn B. , and KoUman P. A. Theoretical and experimental studies of biotin analogues that bind almost as tightly to streptavidin as biotin[ J ]. J. Org. Chem. 2002,67,1827-1837

二级参考文献11

  • 1Mistry P S, Dakshinamurti K. Biochemistry of biotin [ J ], Vitam. Horm. , 1964,22 : 1-55.
  • 2Coggeshall, C J, Heggers P J, Robson, C M, et al. Biotin status and plasma glucose in diabetics [ J ]. Ann. NY Acad. Sci. , 1985,447:389-392.
  • 3Maebashi M, Makino Y, Furukawa Y, et al. Therapeutic evaluation of the effect of biotin on hyperglycemia in patients with non-insulin dependent diabetes mellitus [ J ]. J. Clin. Biochem. Nutr. , 1993,14:211-218.
  • 4McCormick D B. Biotin [ J ] . Nutr. Rev. , 1975,33 : 97 - 102.
  • 5欧洲药典委员会,欧洲药典[S],EP5.0,2005:1073,1100.1101.
  • 6美国药典委员会,美国药典[S],USP28,2005:230.
  • 7Cheney L C, Piening J R. The total synthesis of 2,3,4,5- tetradedrobiotin [ J ]. J Am. Chem. Soc. , 1945, 67:731-735.
  • 8Nishimura S,Imoto E. Studies on thiophene compounds. XIX. syntheses of 2,3,4,5-tetradehydrobiotin and 2,3,4, 5-tetradehydronorbiotin [ J ]. Bull. Chem. Soc. Jpn. , 1962, 35:432-437.
  • 9Hanka L J, D G Martin, L M Reineke. Two new antimetabolites of biotin: α-methyldethiobiotin and α- methylbiotin [ J ]. Antimicrob. Agents Chemother. , 1972,1 : 135-138.
  • 10Dixon R W, Radmer R J, Kuhn B, et al. Theoretical and experimental studies of biotin analogues that bind almost as tightly to streptavidin as biotin [ J ] J. Org. Chem,2002,67 : 1827-1837.

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化学研究与应用
2009年 第3期

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