(2R,3R) γ-hydroxyvaline | 74431-59-7

• 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: (2R,3R) γ-hydroxyvaline
• 英文别名: D-iso-γ-hydroxy-valine；γ-hydroxy-D-valine；(2R,3R)-4-hydroxyvaline；4-hydroxy-D-valine；(2R,3R)-2-Amino-4-hydroxy-3-methylbutanoic acid
• CAS: 74431-59-7
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: YMRZLZUJZNHRLO-IUYQGCFVSA-N

物化性质

• 熔点：
  274 °C
• 沸点：
  343.3±32.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

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：

  Z-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 (2R,3R) γ-hydroxyvaline
  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

• Exploration of the Molecular Origin of the Azinomycin Epoxide: Timing of the Biosynthesis Revealed
  作者：Vasudha Sharma、Gilbert T. Kelly、Coran M. H. Watanabe

  DOI：10.1021/ol8018852

  日期：2008.11.6

  Streptomyces sahachiroi whole cell feeding experiments, utilizing putative precursors labeled with stable isotopes, established that the epoxide unit of the DNA cross-linked agents, azinomycin A and B, proceeds via a valine-dependent pathway and that hydroxylation and dehydration precedes formation of the terminal epoxide. Sodium 3-methyl-2-oxobutenoate, formed through a transimination reaction, was shown to be the penultimate precursor incorporated into the azinomycin epoxide.
• 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：——
• Synthesis of ω-hydroxy analogues of valine, leucine and isoleucine
  作者：Sabine Englisch-Peters

  DOI：10.1016/s0040-4020(01)85125-5

  日期：1989.1