D-allo-γ-hydroxy-valine | 127181-56-0

• 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: D-allo-γ-hydroxy-valine
• 英文别名: γ-hydroxy-D-valine；(2R,3S)-4-hydroxyvaline；4-hydroxy-D-valine；(2R,3S)-2-Amino-4-hydroxy-3-methylbutanoic acid
• CAS: 127181-56-0
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: YMRZLZUJZNHRLO-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  E-2-phenyl-4(2-acetoxy-1-methylethylidene)-2-oxazoline-5-one 在 palladium on activated charcoal 盐酸 、 氢气 、 双氧水 、 氧气 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 57.0h， 生成 D-allo-γ-hydroxy-valine
  参考文献：
  名称：

  Synthesis of ω-hydroxy analogues of valine, leucine and isoleucine

  摘要：

  DOI：

  10.1016/s0040-4020(01)85125-5

文献信息

• Synthesis and Solid-Phase Application of Suitably Protected γ-Hydroxyvaline Building Blocks
  作者：Mare Cudic、Frank Marí、Gregg B. Fields

  DOI：10.1021/jo070436y

  日期：2007.7.1

  Recently, an unexpected modified residue, gamma-hydroxy-D-valine (D-Hyv), was identified within ribosomally expressed polypeptide chains of four conopeptides from the venoms of Conus gladiator and Conus mus. To assemble Hyv-containing peptides, we have explored several routes for the synthesis of appropriately functionalized Hyv building blocks. D-Hyv was produced from D-Val by using a variation of the previously published K2PtCl4/CuCl2 oxidative method. Direct synthesis of Boc- or Cbz-D-Hyv lactone proceeded in low yield; additionally, the lactones are too unreative for solid-phase applications. 9-Borabicyclononane or copper-complexed D-Hyv was prepared and treated with tert-butyldimethylsilyl trifluoromethanesulfonate (TBDMSOTf) to produce D-Hyv(O-TBDMS). The most efficient complex disruption was achieved by Chelex 110 resin (Na+ form) treatment of copper-complexed D-Hyv(O-TBDMS). Reaction of D-Hyv(O-TBDMS) with Fmoc-OSu produced Fmoc-D-Hyv(O-TBDMS) in 26% yield from D-Val. The Fmoc-D-Hyv(O-TBDMS) diastereomers were separated by preparative RP-HPLC in 13% yield from D-Val. Fmoc-D-Hyv(O-TBDMS) was used for the synthesis of the conopeptide gld-V* from Conus gladiator. The isolated synthetic and natural products had coincidental mass and NMR spectra. The methodology presented herein will greatly facilitate biological studies of Hyv-containing sequences, such as receptor responses to hydroxylated versus nonhydroxylated conopeptides and the relative susceptibility of proteins to modification by oxidative stress.
• Usher, John J., Journal of Chemical Research, Miniprint, 1980, # 1, p. 361 - 377
  作者：Usher, John J.

  DOI：——

  日期：——