Fmoc-L-Ser(tBu)-L-Agl-OH | 1239278-28-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Fmoc-L-Ser(tBu)-L-Agl-OH
• 英文别名: Fmoc-Ser(tBu)-Gly(allyl)-OH；(2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]propanoyl]amino]pent-4-enoic acid
• CAS: 1239278-28-4
• 化学式: C₂₇H₃₂N₂O₆
• 分子量: 480.561
• InChiKey: AAKLEGXJNXYATN-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  113.96
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丁烯 、 Fmoc-L-Ser(tBu)-L-Agl-OH 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以86%的产率得到Fmoc-L-Ser(tBu)-L-Pre-OH
  参考文献：
  名称：

  5,5-Dimethylproline dipeptides: an acid-stable class of pseudoproline

  摘要：

  Commercially available Fmoc-protected L-amino acids were employed and coupled to L-allylglycine. Cross metathesis with 2-methyl-2-butene using second generation Grubbs' catalyst gave L-prenylglycine-containing dipeptides. Treatment with trifluoromethanesulfonic acid resulted in cyclisation and subsequent formation of acid-stable 5,5-dimethyl-L-proline dipeptides for direct insertion into linear peptide sequences. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.068
• 作为产物：
  描述：

  (S)-(-)-2-氨基-4-戊烯酸 、 FMOC-Ser(t-Bu)-F 在 sodium carbonate 、 盐酸 作用下， 以 水 、 丙酮 、 二氯甲烷 为溶剂， 反应 4.0h， 以82%的产率得到Fmoc-L-Ser(tBu)-L-Agl-OH
  参考文献：
  名称：

  5,5-Dimethylproline dipeptides: an acid-stable class of pseudoproline

  摘要：

  Commercially available Fmoc-protected L-amino acids were employed and coupled to L-allylglycine. Cross metathesis with 2-methyl-2-butene using second generation Grubbs' catalyst gave L-prenylglycine-containing dipeptides. Treatment with trifluoromethanesulfonic acid resulted in cyclisation and subsequent formation of acid-stable 5,5-dimethyl-L-proline dipeptides for direct insertion into linear peptide sequences. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.068

文献信息

• 5,5-Dimethylproline dipeptides: an acid-stable class of pseudoproline
  作者：Bianca J. van Lierop、W. Roy Jackson、Andrea J. Robinson

  DOI：10.1016/j.tet.2010.05.068

  日期：2010.7

  Commercially available Fmoc-protected L-amino acids were employed and coupled to L-allylglycine. Cross metathesis with 2-methyl-2-butene using second generation Grubbs' catalyst gave L-prenylglycine-containing dipeptides. Treatment with trifluoromethanesulfonic acid resulted in cyclisation and subsequent formation of acid-stable 5,5-dimethyl-L-proline dipeptides for direct insertion into linear peptide sequences. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.