N-hydroxysuccinimyl N-(((9-fluorenylmethyl)oxy)carbonyl)-L-threoninate | 86088-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-hydroxysuccinimyl N-(((9-fluorenylmethyl)oxy)carbonyl)-L-threoninate
• 英文别名: N-(fluorenylmetoxycarbonyl)-N-(hydroxysuccinimyl)-L-threoninate；Fmoc-Thr-OSu；N-hydroxysuccinimyl N-{[(9-fluorenylmethyl)oxy]carbonyl}-L-threoninate；(2,5-dioxopyrrolidin-1-yl) (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxybutanoate
• CAS: 86088-53-1
• 化学式: C₂₃H₂₂N₂O₇
• 分子量: 438.437
• InChiKey: BUNICUITCWNNLX-ASSNKEHSSA-N

物化性质

• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  122.24
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-hydroxysuccinimyl N-(((9-fluorenylmethyl)oxy)carbonyl)-L-threoninate 在 sodium hydrogen selenide 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 生成
  参考文献：
  名称：

  An improved practical synthesis of protected α-amino selenocarboxylates and its application to the synthesis of N-(α-aminoacyl)sulfonamides

  摘要：

  An improved practical synthetic method was developed for the preparation of selenocarboxylates of amino acids through the reaction of the corresponding activated esters with sodium hydrogen selenide in alcoholic or aqueous medium. The protected cc-amino selenocarboxylates reacted readily with sulfonyl azide to form N-(alpha-aminoacyl)sulfonamides in high yields. The commonly used protecting groups in amino acid and peptide chemistries are well tolerated under these reaction conditions. No protecting groups are needed for the side chains of Arg, Met, Set, Tyr, and Trp. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.07.080
• 作为产物：
  描述：

  N-hydroxysuccinimyl N-(((9-fluorenylmethyl)oxy)carbonyl)-O-(tert-butyl)-L-threoninate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到N-hydroxysuccinimyl N-(((9-fluorenylmethyl)oxy)carbonyl)-L-threoninate
  参考文献：
  名称：

  Chemical synthesis of some mono- and digalactosyl O-glycopeptides

  摘要：

  DOI：

  10.1021/jo00163a027

文献信息

• A novel high-yield synthesis of aminoacyl <i>p</i>-nitroanilines and aminoacyl 7-amino-4-methylcoumarins: Important synthons for the synthesis of chromogenic/fluorogenic protease substrates
  作者：Xinghua Wu、Yu Chen、Herve Aloysius、Longqin Hu

  DOI：10.3762/bjoc.7.117

  日期：——

  Common protecting groups used in amino acid/peptide chemistry were all well-tolerated. The method was also successfully applied to the synthesis of a dipeptide conjugate, indicating that the methodology is applicable to the synthesis of chromogenic substrates containing short peptides. The method has general applicability to the synthesis of chromogenic and fluorogenic peptide substrates and represents

  氨基酰基对硝基苯胺 (aminoacyl-pNA) 和氨基酰基 7-amino-4-methylcoumarin (aminoacyl-AMC) 是合成显色/荧光蛋白酶底物的重要合成子。开发了一种新的有效方法，从氨基酸或其相应的市售 N-羟基琥珀酰亚胺酯开始，以优异的产率合成氨酰基-pNA 和氨酰基-AMC 衍生物。该方法涉及受保护氨基酸的硒代羧酸中间体的原位形成以及随后与叠氮化物的非亲核酰胺化。氨基酸/肽化学中使用的常见保护基团都具有良好的耐受性。该方法还成功应用于二肽偶联物的合成，表明该方法适用于含有短肽的显色底物的合成。
• 13C-N.m.r.-spectral study of the mode of binding of Gd3+ and Mn2+ to a tri-O-d-galactosylated hexapeptide
  作者：Kilian Dill、Marsha E. Daman、Ron L. Batstone-Cunningham、Michel Denarié、André A. Pavia

  DOI：10.1016/0008-6215(83)88388-8

  日期：1983.11