erythro-γ-hydroxy-L-ornithine | 135582-83-1

• 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: erythro-γ-hydroxy-L-ornithine
• 英文别名: γ-hydroxy-erythro-L-ornithine；erythro-3-Hydroxy-L-ornithin；γ-Hydroxy-L-ornithin；L-erythro-2,5-diamino-4-hydroxy-valeric acid；L-erythro-2,5-Diamino-4-hydroxy-valeriansaeure；L-erythro-4-Hydroxy-ornithin；(2s,4r)-4-Hydroxyornithine；(2S,4R)-2,5-diamino-4-hydroxypentanoic acid
• CAS: 135582-83-1
• 化学式: C₅H₁₂N₂O₃
• 分子量: 148.162
• InChiKey: ZVDGZUVHJGGWSG-DMTCNVIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  erythro-γ-hydroxy-L-ornithine 、 氯甲酸苄酯 生成 N,N'-di(benzyloxycarbonyl)-γ-hydroxy-erythro-L-ornithine
  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
• 作为产物：
  描述：

  N2,N5-二苯甲酰-4-氧代-L-鸟氨酸甲酯 在 盐酸 、 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 9.0h， 生成 erythro-γ-hydroxy-L-ornithine
  参考文献：
  名称：

  通过γ-羟基鸟氨酸的相应异构体合成γ-羟基精氨酸的四种立体异构体

  摘要：

  非对映异构 γ-羟基-L-和 D-鸟氨酸是通过用硼氢化钠还原由 L-和 D-组氨酸合成的相应 γ-氧代鸟氨酸来制备的。通过碱性转化后的自动氨基酸分析，估计从 L-组氨酸获得的产物的异构体组成为 68% 赤型和 32% 苏型异构体，而 D-组氨酸产品的异构体组成为 65% 赤型和 35% 苏型异构体氨基酸转化为中性 Nδ-乙酰基衍生物。每种 γ-羟基鸟氨酸的非对映异构体在 Dowex 50 柱上通过色谱法分离，四种旋光异构体被分离为结晶状态的盐酸盐。这些异构体与 1-脒基-3 的胍基化，5-二甲基吡唑硝酸盐 (ADPN) 得到 γ-羟基精氨酸的相应旋光异构体，其作为结晶盐酸盐被分离。赤型-γ-羟基-L-精氨酸盐酸盐显示出与γ-羟基精氨酸的天然产物非常接近的比旋光度。

  DOI：

  10.1246/bcsj.54.470

文献信息

• γ-Hydroxyarginine, a New Guanidino Compound from a Sea-cucumber. I. Isolation and Identification
  作者：Yoshimasa Fujita

  DOI：10.1246/bcsj.32.439

  日期：1959.5

  A new guanidino compound was isolated from a sea-cucumber, Polycheira rufescens, and identified as γ-hydroxyarginine. γ-Hydroxyornithine and γ-guanidino-β-hydroxybutyric acid produced enzymically from the guanidino compound were also isolated and identified. It was, further, concluded that the new guanidino compound susceptible to arginase and l-amino acid oxidase should be γ-hydroxy-l-arginine, although the configuration of the γ-hydroxy group was not yet decided.

  从海参波利切拉（Polycheira rufescens）中分离出了一种新的胍基化合物，并确定其为γ-羟基精氨酸；还分离并确定了由该胍基化合物酶解产生的γ-羟基鸟氨酸和γ-胍基-β-羟基丁酸。进一步的结论是，对精氨酸酶和 l-氨基酸氧化酶敏感的新的胍基化合物应该是γ-羟基-精氨酸，尽管γ-羟基的构型尚未确定。
• Differentiation among the four diastereomers of benzyloxycarbonyl-protected γ-hydroxyornithine in negative-ion fast atom bombardment mass spectrometry
  作者：Hideaki Tsunematsu、Ryuichi Isobe、Koichi Mizusaki、Satoru Makisumi、Magobei Yamamoto

  DOI：10.1002/oms.1210290509

  日期：1994.5

  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.
• Synthesis of Four Stereoisomers of γ-Hydroxyarginine<i>via</i>the Corresponding Isomers of γ-Hydroxyornithine
  作者：Koichi Mizusaki、Satoru Makisumi

  DOI：10.1246/bcsj.54.470

  日期：1981.2

  estimated to be 68% erythro and 32% threo isomers and that of the product from D-histidine 65% erythro and 35% threo isomers by automatic amino acid analysis after conversion of the basic amino acids into neutral Nδ-acetyl derivatives. The diastereoisomers of each γ-hydroxyorni thine were separated by chromatography on a Dowex 50 column, four optically active isomers being isolated as their hydrochlorides

  非对映异构 γ-羟基-L-和 D-鸟氨酸是通过用硼氢化钠还原由 L-和 D-组氨酸合成的相应 γ-氧代鸟氨酸来制备的。通过碱性转化后的自动氨基酸分析，估计从 L-组氨酸获得的产物的异构体组成为 68% 赤型和 32% 苏型异构体，而 D-组氨酸产品的异构体组成为 65% 赤型和 35% 苏型异构体氨基酸转化为中性 Nδ-乙酰基衍生物。每种 γ-羟基鸟氨酸的非对映异构体在 Dowex 50 柱上通过色谱法分离，四种旋光异构体被分离为结晶状态的盐酸盐。这些异构体与 1-脒基-3 的胍基化，5-二甲基吡唑硝酸盐 (ADPN) 得到 γ-羟基精氨酸的相应旋光异构体，其作为结晶盐酸盐被分离。赤型-γ-羟基-L-精氨酸盐酸盐显示出与γ-羟基精氨酸的天然产物非常接近的比旋光度。