L-valinate | 17333-21-0

• 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-valinate
• 英文别名: L-Valin-Anion；L-valine; deprotonated form；(2S)-2-amino-3-methylbutanoate
• CAS: 17333-21-0
• 化学式: C₅H₁₀NO₂
• 分子量: 116.14
• InChiKey: KZSNJWFQEVHDMF-BYPYZUCNSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  pentacyanoaquaferrate(II) 、 L-valinate 在 LiClO₄ 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Pentacyanoferrate(II) complexes of amino acids

  摘要：

  DOI：

  10.1021/ja00390a020
• 作为产物：
  描述：

  2-amino-3-methylbutyric acid-[3-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-2,6-dioxo-piperidine-1-yl-methyl]ester hydrochloride 在 phosphate buffer 作用下， 以 水 为溶剂， 生成 聚合甲醛 、 沙利度胺 、 L-valinate
  参考文献：
  名称：

  Synthesis and immunological activity of water-soluble Thalidomide prodrugs

  摘要：

  A series of new water-soluble thalidomide prodrugs was prepared. All compounds were derivatized on the nitrogen of the glutarimide ring. Esters of natural amino acids and succinic acid derivatives have been introduced by reaction with the hydroxymethyl thalidomide 2. Nicotinic acid derivatives were prepared from halomethyl derivatives. Additionally, a methoxy methyl derivative and a carboxymethyl derivative were prepared directly from thalidomide. Most compounds showed a very large increase in water solubility compared to thalidomide itself (0.012 mg/mL). The amorphous hydrochlorides of the N-methylalanine ester 8, valine ester 9, and glycylglycine ester 10, respectively, were the most soluble compounds showing solubility greater than 300 mg/mL, which equals an increase greater than 15,000-fold. The lipophilicity of the prodrugs has been determined by their HPLC capacity factors k '. The stability of selected compounds was determined. The hydrolysis rates follow pseudo-first order kinetics. In order to assess the immunological activity, the prodrugs were tested using tumor necrosis factor-alpha and interleukin-2 inhibition assays. Selected compounds were additionally investigated on their abililty to inhibit the local Shwartzman reaction, an assay to determine the Vascular permeability. The prodrugs retained high effectiveness in the inhibition of TNF-alpha release. Our results indicated that the more stable prodrugs exhibited higher activity in the immunological assays. Some compounds showed higher activity than thalidomide itself, suggesting a high affine binding to the pharmacophore. In conclusion, the prodrugs exhibited high water solubility and high activity and might therefore be used in therapeutic applications. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00342-4

文献信息

• The Stereochemistry and Reactivity of Metal-Schiff Base Complexes. VII. Contribution of Hydrophobic Interligand Interaction to Chiral Recognition of Phenylalaninate and Tryptophanate with (1<i>R</i>,2<i>R</i>)-<i>N</i>,<i>N</i>′-Disalicylidene-1,2-cyclohexanediaminecobalt(III) Complex
  作者：Yuki Fujii、Yuzo Yoshikawa、Masato Syoji、Homare Shinohara

  DOI：10.1246/bcsj.63.138

  日期：1990.1

  The stability constants, K1, of Δ-β2-diastereomers of mixed ligand cobalt(III) complexes with a chiral quadridentate Schiff base (sal-(R,R)-chxn), derived from salicylaldehyde and (R,R)-1,2-cyclohexanediamine, and d- or l-amino acidate (aa−=gly, ala, val, leu, thr, phe, trp, pro, asp, asn, and glu) were determined spectrophotometrically in water–methanol (2:3 by volume) containing acetate buffer (0.3 mol dm−3) at 22°C: trans-[Cosal-(R,R)-chxn}(H2O)2]++aa−\oversetK1\ightleftharpoonsΔ-β2-[Cosal-(R,R)-chxn}(aa)]. The K1 values range from 5.6×106 to 1.2×109 mol−1 dm3 and obey a linear free energy relationship except for d-phe, d-trp, d-asp, d-asn, and d-pro. In the cases of d-phe, d-trp, d-asp, and d-asn, their stability constants are 5–30 times as high as those for the corresponding l-aa. Extraordinary stabilization of the d-phe and d-trp complexes is discussed in terms of the interligand stacking of the aromatic rings between the Schiff base ligand and a side chain of amino acidate on the basis of conformational analysis and 1H NMR spectra.

  Δ-β2-型混配体钴(III)配合物的稳定常数K1是通过光谱法在22°C下，在含有乙酸盐缓冲液(0.3 mol dm−3)的水-甲醇(2:3体积比)混合溶液中测定的。这些配合物由手性四齿席夫碱(sal-(R,R)-chxn)和d-或l-氨基酸根(aa− = gly、ala、val、leu、thr、phe、trp、pro、asp、asn和glu)组成。sal-(R,R)-chxn是由水杨醛和(R,R)-1,2-环己二胺衍生而来。 K1值范围在5.6×106到1.2×109 mol−1 dm3之间，除了d-phe、d-trp、d-asp、d-asn和d-pro外，都符合线性自由能关系。对于d-phe、d-trp、d-asp和d-asn，它们的稳定常数是相应l-氨基酸的5-30倍。 基于构象分析和1H NMR光谱，文章讨论了d-phe和d-trp配合物的特殊稳定性，认为这与席夫碱配体和氨基酸侧链之间的芳香环层间堆积有关。
• Meiske, Larry A.; Angelici, Robert J., Inorganic Chemistry, 1982, vol. 21, # 2, p. 731 - 737
  作者：Meiske, Larry A.、Angelici, Robert J.

  DOI：——

  日期：——