期刊文献+
任意字段
题名或关键词
题名
关键词
文摘
作者
第一作者
机构
刊名
分类号
参考文献
作者简介
基金资助
栏目信息

二肽物±(4S)-5-[叔丁基二甲基硅氧-4-二苄氨基-2-甲酰氨基-N-3-羟基-2-(三苯甲烷基)丙基]戊酰胺的合成 被引量：2

Synthesis of Dipeptide ±(4S)-5-(TBDMS)oxy-4-(dibenzylamino)-2-formamidoN-[3-hydroxy-2-(tritylamino)propyl]pentanamide
下载PDF
导出
摘要 以D-丝氨酸为起始原料,经酯化、还原、氧化、缩合、水解等九步反应,合成了非天然氨基酸τ-L-His-D-Ala的关键前体——二肽物±(4S)-5-[(叔丁基二甲基硅氧)-4-(二苄氨基)-2-甲酰氨基-N-3-羟基-2-(三苯甲烷基)丙基]戊酰胺,总收率35.3%,其结构经1H NMR,13C NMR和MS表征。 A precursor of unnatural amino acid τ-L-His-D-Ala,dipeptide ±（4S）-5-（TBDMS）oxy-4-（dibenzylamino）-2-formamido-N-[3-hydroxy-2-（tritylamino）propyl]pentanamide,was synthesized from D-serine by a nine-step reaction of esterification,reduction,Swern oxidation,condensation,hydrolysis,and so on in total yield of 35.3%.The structure was characterized by 1H NMR,13C NMR and MS.
作者 王月慧 马兵 吴菊 刘建武 沈介发 严生虎 张跃
机构地区 常州大学制药与生命科学学院
出处 《合成化学》 CAS CSCD 北大核心 2013年第1期11-15,25,共6页 Chinese Journal of Synthetic Chemistry
基金 国家自然科学基金资助项目(21102010)
关键词 非天然氨基酸 τ-L-His-D-Ala 二肽 合成 unnatural amino acid τ-L-His-D-Ala dipeptide synthesis
分类号 O629.72 [理学—有机化学]
  • 相关文献

参考文献13

  • 1Matsunaga S,Fusetani N,Hashimoto K. A novel antifungal bicyclic peptide from a marine sponge theonella Sp[J].Journal of the American Chemical Society,1989.2582-2588.
  • 2Wada S,Kantha S S,Yamaahita T. Accumulation of H + in vacuoles induced by a marine peptide toxin,theonellamide F,in rat embryonic 3 Y1 fibroblasts[J].Marine Biotechnology,2002.571-582.
  • 3Schmidt E W,Obraztsova A Y,Davidson S K. Identification of the antifungal peptide-containing symbiont of the marine sponge theonella swinhoei as a novel-proteobacterium,candidatus entotheonella palauensis[J].Marine Biology,2000.337-341.
  • 4Proksch P,Edrada-Ebel R,Ebel R. Drugs from the sea-opportunities and obstacles[J].Marine Drugs,2003.5-17.
  • 5Tohdo K,Hamada Y,Shioiri T. Theonellamide F synthetic studies.Stereoselective synthesisof (3S,4S,5E,7E)-3-amino-8-(4-bromophenyl)-4-hydroxy-6-methyl-5,7-octadienoic acid (Aboa)[J].Tetrahedron Letters,1992.2031-2034.
  • 6Tohdo K,Hamada Y,Shioiri T. Synthesis of the southern hemisphere of theonellamide F,a bicyclic dodecapeptide of marine oOrigin[J].Synlett:Accounts and Rapid Communications In Synthetic Organic Chemistry,1994.247-249.
  • 7戢峻,鲁尔贝,万雯婷,黎明,雷昊,丁一刚,熊家林.L-丝氨酸甲酯盐酸盐的合成工艺研究[J].化学与生物工程,2008,25(2):51-53. 被引量：6
  • 8La(i)b T,Chastanet J,Zhu J. Diastereoselective synthesis of hydroxy-amino alcohols and (2S,3S)-hydroxyleucine from chiral D-(N,N-dibenzylamino) serine (TBDMS) aldehyde[J].Journal of Organic Chemistry,1998.1709-1713.
  • 9Panella L,Aleixandre A M,Kruidhof G J. Enantioselective Rh-catalyzed hydrogenation of N-gormyl dehydroamino esters with monodentate phosphoramidite ligands[J].Journal of Organic Chemistry,2006.2026-2036.
  • 10Reetz M T,Kayser F,Harms K. Cycioaddition reactions of y-amino α,β-didehydro amino acid esters:A test case for the principle of 1,3-allylic strain[J].Tetrahedron Letters,1992.3453-3456.

二级参考文献4

共引文献5

同被引文献27

  • 1温远庆,谢庆兰,邓锋杰.位阻型硅烷保护剂[J].有机硅材料,2004,18(6):21-23. 被引量：8
  • 2罗六保,邓锋杰,曾小剑.二甲基叔丁基氯硅烷的合成方法及应用[J].有机硅材料,2005,19(3):45-47. 被引量：1
  • 3Matsunaga S,Fusetani N,Hashimoto K,etal.A novel antifungal bicyclic peptide from a marine sponge Theonella Sp[J].J Am Chem Soc,1989,(111):2582-2588.
  • 4Schmidt E W,Bewley C A,Faulkner D J.Theopalauamide,a bicyclic glycopeptide from filamentous bacterial symbionts of the lithistid sponge Theonella swinhoei from palau and mozambique[J].J Org Chem,1998,63:1254-1258.
  • 5Schmidt E W,Obraztsova A Y,Davidson S K,et al.Identification of the antifungal peptide-containing symbiont of the marine sponge Theonella swinhoei as a novel proteobacterium,candidatus entotheonella palauensis[J].Mar Biol,2000,1:337-341.
  • 6Tohdo K,Hamada Y,Shioiri T.Theonellamide F synthetic studies.Stereoselective synthesis of (3S,4S,5E,7E)-3-amino-8-(4-bromophenyl)-4-hydroxy-6-methyl5,7-octadienoic acid (aboa)[J].Tetrahedron Lett,1992,33:2031-2034.
  • 7Tohdo K,Hamada Y,Shioiri T.Stereoselective synthesis of (2S,4R)-2-amino-4-hydroxyadipic acid,the characteristic amino acid of theonellamide F[J].Synlett,1994:105-106.
  • 8Tohdo K,Hamada Y,Shioiri T.Synthesis of the southem hemisphere of theonellamide F,a bicyclic dodecapeptide of marine origin[J].Synlett,1994:247-249.
  • 9Tohdo K,Hamada Y,Shioiri T.Synthesis of the northem hemisphere of theonellamide F,a bicyclic dodecapeptide of marine origin[J].Synlett,1994:250.
  • 10Arnold L D,Kalantar T H,Vederas J C.Conversion of serine to stereochemically pure β-substituted α-amino acids via β-lactones[J].J Am Chem Soc,1985,(107):7105-7109.

引证文献2

二级引证文献4

合成化学
2013年 第1期

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部