L-isoleucine 1,5-naphthalenedisulfonate | 72209-58-6

• 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: L-isoleucine 1,5-naphthalenedisulfonate
• 英文别名: (2S,3S)-2-amino-3-methylpentanoic acid;naphthalene-1,5-disulfonic acid
• CAS: 72209-58-6；73732-98-6；85680-44-0；92387-92-3；92387-93-4
• 化学式: 2C₆H₁₃NO₂*C₁₀H₈O₆S₂
• 分子量: 550.651
• InChiKey: GSKFLPYZEGTDRE-CKDWGAALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  189
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  L-isoleucine 1,5-naphthalenedisulfonate 在 Ile-mixture 、 水杨醛 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 L-alloisoleucine 1,5-naphthalenedisulfonate
  参考文献：
  名称：

  不对称转化制备DL-异亮氨酸

  摘要：

  异亮氨酸的化学合成导致 DL-异亮氨酸和 DL-异亮氨酸的混合物。研究了从混合物中制备 DL-异亮氨酸。当混合物与水中的 1,5-萘二磺酸反应时，DL-异亮氨酸形成溶解度较低的 1,5-萘二磺酸盐，可以以盐的形式从混合物中分离出来。在水杨醛和游离异亮氨酸混合物的存在下，通过在乙酸中加热，可容易地使可溶性 DL-别异亮氨酸盐差向异构化。两种非对映异构体外消旋体之间的不对称转化通过溶解性较差的 DL-异亮氨酸盐的分级结晶和可溶性 DL-异亮氨酸盐的差向异构化的同时组合进行。

  DOI：

  10.1246/bcsj.57.1328
• 作为产物：
  描述：

  L-异亮氨酸 、 1,5-萘二磺酸 以 甲醇 、 水 为溶剂， 反应 0.17h， 以79%的产率得到L-isoleucine 1,5-naphthalenedisulfonate
  参考文献：
  名称：

  Chiral supramolecular compounds comprising naphthalene-1,5-disulfonic acid and various α-amino acids: influence of substituents of α-amino acids on the structures, circular dichroism and luminescent properties

  摘要：

  Self assembly of naphthalene-1,5-disulfonic acid (1,5-H2NDS) and 11 chiral alpha-L-amino acids generates 12 chiral supramolecular compounds, namely, 2(HAla)(+)center dot(NDS)(2-) (1), 4(HSer)(+)center dot 2(NDS)(2-)center dot 2(H2O) (2), 2(HPhe)(+)center dot(NDS)(2-) (3), 2(HTyr)(+)center dot(NDS)(2-) (4), 2(H(2)Cys)(2+)center dot 2(NDS)(2-)center dot 2(H2O) (5), 2(HVal)(+)center dot(NDS)(2-)center dot 2(Val)center dot 4(H2O) (6), 2(HThr)(+)center dot(NDS)(2-) (7), 2(HLeu)(+)center dot(NDS)(2-)center dot 2(HLle) (9), 2(HLle)(+)center dot(NDS)(2-)center dot(H2O) (9), 2(HArg)(+)center dot(NDS)(2-)center dot 3(H2O) (10), (H(2)His)(2+)center dot(NDS)(2-)center dot 2(H2O) (11), and 2(H(2)His)(2+)center dot 2(NDS)(2-)center dot 6(H2O) (12), which have been characterized by elemental analysis, IR, TG, PL, circular dichroism (CD), powder and single-crystal X-ray diffraction. Structural analyses indicate that substituents of alpha-amino acids influence the supramolecular patterns formed by -SO3 and -NH3 groups and supramolecular networks. Compounds 1-12 crystallize in different chiral P1, P2(1)2(1)2(1), P3(2) and P2(1) space groups, respectively. The patterns formed by -SO3 and -NH3 groups are more abundant, such as 1D double chain in 1, 3 and 4, [(SO3)(4)(NH3)(4)] cage in 2, [((SO3)(4)(NH3)(4)] motif in 5, [(SO3)(4)(NH3)(4)] motif in 6, 1D cylinder in 7, [(SO3)(NH3)] motif in 8,11 and 12, 1D single and double chain in 9, as well as [(SO3)(2)(NH3)(2)] motif in 10. Compounds 1-9 exhibit different pillared layered networks, in which weak pi center dot center dot center dot pi and C-H center dot center dot center dot pi interactions are detected except for compounds 4, 6, 8 and 9. Compound 11 presents an interesting network constructed from the interconnection of two types of DNA shaped double helixes. It should be indicated that exposure of 12 under atmosphere can transform into compound 11, in which the configuration of H(2)His(2+) cations varies from R to S. CD spectra indicate that the solid samples of compounds 3, 4 and 6-11 display dichroic signals in their CD spectra. Luminescent investigation reveals that compounds 1-11 exhibit stronger emission than the 1,5-H2NDS with the emission maximum varying from 342 to 413 nm. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.051

文献信息

• JPS54109953A
  申请人：——

  公开号：JPS54109953A

  公开（公告）日：1979-08-29
• JPS588048A
  申请人：——

  公开号：JPS588048A

  公开（公告）日：1983-01-18
• Chiral supramolecular compounds comprising naphthalene-1,5-disulfonic acid and various α-amino acids: influence of substituents of α-amino acids on the structures, circular dichroism and luminescent properties
  作者：Ya-Nan Li、Li-Hua Huo、Xin Zou、Zhao-Peng Deng、Zhi-Biao Zhu、Shan Gao

  DOI：10.1016/j.tet.2015.09.051

  日期：2015.11

  Self assembly of naphthalene-1,5-disulfonic acid (1,5-H2NDS) and 11 chiral alpha-L-amino acids generates 12 chiral supramolecular compounds, namely, 2(HAla)(+)center dot(NDS)(2-) (1), 4(HSer)(+)center dot 2(NDS)(2-)center dot 2(H2O) (2), 2(HPhe)(+)center dot(NDS)(2-) (3), 2(HTyr)(+)center dot(NDS)(2-) (4), 2(H(2)Cys)(2+)center dot 2(NDS)(2-)center dot 2(H2O) (5), 2(HVal)(+)center dot(NDS)(2-)center dot 2(Val)center dot 4(H2O) (6), 2(HThr)(+)center dot(NDS)(2-) (7), 2(HLeu)(+)center dot(NDS)(2-)center dot 2(HLle) (9), 2(HLle)(+)center dot(NDS)(2-)center dot(H2O) (9), 2(HArg)(+)center dot(NDS)(2-)center dot 3(H2O) (10), (H(2)His)(2+)center dot(NDS)(2-)center dot 2(H2O) (11), and 2(H(2)His)(2+)center dot 2(NDS)(2-)center dot 6(H2O) (12), which have been characterized by elemental analysis, IR, TG, PL, circular dichroism (CD), powder and single-crystal X-ray diffraction. Structural analyses indicate that substituents of alpha-amino acids influence the supramolecular patterns formed by -SO3 and -NH3 groups and supramolecular networks. Compounds 1-12 crystallize in different chiral P1, P2(1)2(1)2(1), P3(2) and P2(1) space groups, respectively. The patterns formed by -SO3 and -NH3 groups are more abundant, such as 1D double chain in 1, 3 and 4, [(SO3)(4)(NH3)(4)] cage in 2, [((SO3)(4)(NH3)(4)] motif in 5, [(SO3)(4)(NH3)(4)] motif in 6, 1D cylinder in 7, [(SO3)(NH3)] motif in 8,11 and 12, 1D single and double chain in 9, as well as [(SO3)(2)(NH3)(2)] motif in 10. Compounds 1-9 exhibit different pillared layered networks, in which weak pi center dot center dot center dot pi and C-H center dot center dot center dot pi interactions are detected except for compounds 4, 6, 8 and 9. Compound 11 presents an interesting network constructed from the interconnection of two types of DNA shaped double helixes. It should be indicated that exposure of 12 under atmosphere can transform into compound 11, in which the configuration of H(2)His(2+) cations varies from R to S. CD spectra indicate that the solid samples of compounds 3, 4 and 6-11 display dichroic signals in their CD spectra. Luminescent investigation reveals that compounds 1-11 exhibit stronger emission than the 1,5-H2NDS with the emission maximum varying from 342 to 413 nm. (C) 2015 Elsevier Ltd. All rights reserved.
• The Preparation of DL-Isoleucine by Asymmetric Transformation
  作者：Chikara Hongo、Ryuzo Yoshioka、Masanori Tohyama、Shigeki Yamada、Ichiro Chibata

  DOI：10.1246/bcsj.57.1328

  日期：1984.5

  The chemical synthesis of isoleucine leads to a mixture of DL-isoleucine and DL-alloisoleucine. The preparation of DL-isoleucine from the mixture was studied. When the mixture was reacted with 1,5-naphthalenedisulfonic acid in water, DL-isoleucine formed the less soluble 1,5-naphthalenedisulfonate and could be separated in the form of the salt from the mixture. The soluble DL-alloisoleucine salt was

  异亮氨酸的化学合成导致 DL-异亮氨酸和 DL-异亮氨酸的混合物。研究了从混合物中制备 DL-异亮氨酸。当混合物与水中的 1,5-萘二磺酸反应时，DL-异亮氨酸形成溶解度较低的 1,5-萘二磺酸盐，可以以盐的形式从混合物中分离出来。在水杨醛和游离异亮氨酸混合物的存在下，通过在乙酸中加热，可容易地使可溶性 DL-别异亮氨酸盐差向异构化。两种非对映异构体外消旋体之间的不对称转化通过溶解性较差的 DL-异亮氨酸盐的分级结晶和可溶性 DL-异亮氨酸盐的差向异构化的同时组合进行。