N2,N5-二[(苄氧基)羰基]鸟氨酸 | 2274-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N2,N5-二[(苄氧基)羰基]鸟氨酸
• 中文别名: N,N'-双-CBZ-D-鸟氨酸；N,N'-双-Cbz-D-鸟氨酸
• 英文名称: N,N'-di(benzyloxycarbonyl)-D-ornithine
• 英文别名: (R)-N,N-Dibenzyloxycarbonylornithine；Z-D-Ornithine(Z)-OH；α,δ-Bis-benzyloxycarbonyl-D-ornithin；(2R)-2,5-bis(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 2274-58-0；39897-05-7；13594-49-5
• 化学式: C₂₁H₂₄N₂O₆
• 分子量: 400.431
• InChiKey: VBENHRFIEOLOJJ-GOSISDBHSA-N

物化性质

• 沸点：
  653.3±55.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N2,N5-二[(苄氧基)羰基]鸟氨酸 在 N-甲基吗啉 、 silver benzoate 、 氯甲酸乙酯 作用下， 以 乙酸乙酯 为溶剂， 生成 (R)-N,N-dibenzyloxycarbonyl-β-lysine methyl ester
  参考文献：
  名称：

  Keirs, David; Moffat, David; Overton, Karl, Journal of the Chemical Society. Perkin transactions I, 1991, # 5, p. 1041 - 1051

  摘要：

  DOI：
• 作为产物：
  描述：

  D-鸟氨酸 、 氯甲酸苄酯 生成 N2,N5-二[(苄氧基)羰基]鸟氨酸
  参考文献：
  名称：

  Differentiation among the four diastereomers of benzyloxycarbonyl-protected γ-hydroxyornithine in negative-ion fast atom bombardment mass spectrometry

  摘要：

  AbstractDiscrimination among the four γ‐hydroxyornithine diastereomers was studied by fast atom bombardment mass spectrometry (FABMS). It is impossible to distinguish among the four diastereomers of this amino acid by positive‐ and negative‐ion FAB and collisionally activated dissociation MS, but benzyloxycarbonyl group protection of the α‐ and δ‐amino groups in γ‐hydroxyornithine allows differentiation among the diastereomers in negative‐ion FABMS. The negative‐ion mass spectra of benzyloxycarbonyl‐protected γ‐hydroxyornithine diastereomers showed differences among the abundances of the molecule ion [M – H]‐, the dehydrated ion [M — H — H2O]‐ due to the loss of the γ‐hydroxyl group and the fragment ions formed from both [M — H]‐ and [M — H — H2O]‐ ions. On the other hand, no difference was found between the fragmentations of the benzyloxycarbonyl‐protected enantiomers of ornithine in negative‐ion FABMS. These results indicate that the orientation of the γ‐hydroxyl group and the existence of two benzene rings in the benzyloxycarbonyl group are important factors which are responsible for the fragmentations of the four benzyloxycarbonyl‐protected γ‐hydroxyornithine diastereomers in negative‐ion FABMS. These studies also showed that the negative‐ion FABMS for benzyloxycarbonyl‐protected γ‐hydroxyornithine diastereomers is a useful method for determining the configuration of each diastereomer of γ‐hydroxyornithine.

  DOI：

  10.1002/oms.1210290509

文献信息

• D-3,6-Diaminohexanoic acid 2-(carboxymethyl)-2-methylhydrazide, process
  申请人：American Cyanamid Company

  公开号：US03962317A1

  公开（公告）日：1976-06-08

  This disclosure describes D-3,6-diaminohexanoic acid 2-(carboxymethyl)-2-methylhydrazide which is useful as an antibacterial agent.

  本披露描述了D-3,6-二氨基己酸2-(羧甲基)-2-甲基肼，该化合物可用作抗菌剂。
• The synthesis of deoxynegamycin and some related compounds.
  作者：VWILLIAM V. CURRAN、JAMES H. BOOTHE

  DOI：10.7164/antibiotics.31.914

  日期：——
• Amino acid, dipeptide and pseudodipeptide conjugates of ring-substituted 8-aminoquinolines: Synthesis and evaluation of anti-infective, β-haematin inhibition and cytotoxic activities
  作者：Kirandeep Kaur、Meenakshi Jain、Shabana I. Khan、Melissa R. Jacob、Babu L. Tekwani、Savita Singh、Prati Pal Singh、Rahul Jain

  DOI：10.1016/j.ejmech.2012.03.019

  日期：2012.6

  Three new series of 8-aminoquinolines with modifications in the side-chain by conjugation with amino acids, dipeptides and pseudodipeptides have been synthesized. The synthesized compounds were tested for in vitro antimalarial activity against chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum strains, in vitro cytotoxicity in mammalian kidney cells (Vero), in vitro antileishmanial activity against Leishmania donovani, in vitro antimicrobial activity and in vitro inhibition of beta-haematin formation. The promising compounds were also evaluated for in vivo blood-schizontocidal antimalarial activity against Plasmodium berghei infected mice. The analogues 55 and 101 produced highest antimalarial activities, in vitro. Analogues 52 and 59 exhibited promising antileishmanial and broad spectrum of antifungal activities, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.
• WO2007/27742
  申请人：——

  公开号：——

  公开（公告）日：——
• US3962317A
  申请人：——

  公开号：US3962317A

  公开（公告）日：1976-06-08