Nα-(9-fluorenylmethoxy)carbonyl-Nε-[(2R)-2,4-dihydroxybutanoyl]-L-lysine | 1350543-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Nα-(9-fluorenylmethoxy)carbonyl-Nε-[(2R)-2,4-dihydroxybutanoyl]-L-lysine
• 英文别名: (2S)-6-[[(2R)-2,4-dihydroxybutanoyl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid
• CAS: 1350543-73-5
• 化学式: C₂₅H₃₀N₂O₇
• 分子量: 470.522
• InChiKey: PLZHLCIOLRJEBW-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Nα-(9-fluorenylmethoxy)carbonyl-Nε-[(2R)-2,4-dihydroxybutanoyl]-L-lysine 、 二甲基硫代磷酰氯 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Preparation of pseudo glycoamino acid and its application to glycopeptide synthesis

  摘要：

  A pseudo glycoamino acid composed of a 1,3-diol structure and an amino acid was synthesized. This amino acid analog can act as an alternative acceptor to an amino acid containing GlcNAc for transglycosylation by Endo-M. A pseudo glycopeptide was synthesized using the pseudo glycoamino acid by a solid phase procedure. We attempted transglycosylation of N-glycan to the peptide using Endo-M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.121
• 作为产物：
  描述：

  Nα-benzyloxycarbonyl-Nε-[(2R)-2,4-O-benzylidene-2,4-dihydroxybutanoyl]-L-lysine benzyl ester 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以62%的产率得到Nα-(9-fluorenylmethoxy)carbonyl-Nε-[(2R)-2,4-dihydroxybutanoyl]-L-lysine
  参考文献：
  名称：

  Preparation of pseudo glycoamino acid and its application to glycopeptide synthesis

  摘要：

  A pseudo glycoamino acid composed of a 1,3-diol structure and an amino acid was synthesized. This amino acid analog can act as an alternative acceptor to an amino acid containing GlcNAc for transglycosylation by Endo-M. A pseudo glycopeptide was synthesized using the pseudo glycoamino acid by a solid phase procedure. We attempted transglycosylation of N-glycan to the peptide using Endo-M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.121

文献信息

• Preparation of pseudo glycoamino acid and its application to glycopeptide synthesis
  作者：Yusuke Tomabechi、Toshiyuki Inazu

  DOI：10.1016/j.tetlet.2011.09.121

  日期：2011.11

  A pseudo glycoamino acid composed of a 1,3-diol structure and an amino acid was synthesized. This amino acid analog can act as an alternative acceptor to an amino acid containing GlcNAc for transglycosylation by Endo-M. A pseudo glycopeptide was synthesized using the pseudo glycoamino acid by a solid phase procedure. We attempted transglycosylation of N-glycan to the peptide using Endo-M. (C) 2011 Elsevier Ltd. All rights reserved.