(2S,3R)-3-hydroxypipecolic acid

• 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: (2S,3R)-3-hydroxypipecolic acid
• 英文别名: (2S,3R)-3-hydroxypiperidine-2-carboxylic acid
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: FDMYUQHVJYNDLI-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-hydroxypipecolic acid 在 磷化氢 、 氢碘酸 作用下， 反应 5.0h， 生成 L-哌啶-2-甲酸
  参考文献：
  名称：

  A new amino acid, (2S,3R)-(-)-3-hydroxybaikiain from Russula subnigricans HONGO.

  摘要：

  从毒蘑菇 Russula subnigricans HONGO 中分离出一种新的氨基酸（I），其特征为 (2S, 3R) - (-) -3-hydroxybaikiain [(2S, 3R) - (-) -1, 2, 3, 6-tetrahydro-3-hydroxypyridine-2-carboxylic acid]。此外，还分离并鉴定了(S)-(-)-白果素(II)、(S)-(-)-哌啶醇酸(III)、麦角甾醇(IV)、过氧化麦角甾醇(V)和麦角甾醇(VI)。

  DOI：

  10.1248/cpb.35.3482
• 作为产物：
  描述：

  (+)-(2S,3R)-3-acetoxypiperidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester 在 lithium hydroxide 、 硫酸 作用下， 以 乙醇 为溶剂， 生成 (2S,3R)-3-hydroxypipecolic acid
  参考文献：
  名称：

  Synthetic studies on tetrazomine: lipase PS resolution of racemic cis-β-hydroxypipecolic acid

  摘要：

  An efficient enzymatic resolution of racemic cis-beta -hydroxypipecolic acid is described affording both the (2S,3R) and (2R,3S) protected amino acids in good yield and high enantiomeric ratios. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01527-6

文献信息

• Regio- and stereoselective oxygenation of proline derivatives by using microbial 2-oxoglutarate-dependent dioxygenases
  作者：Ryotaro Hara、Naoko Uchiumi、Naoko Okamoto、Kuniki Kino

  DOI：10.1080/09168451.2014.918490

  日期：2014.8.3

  We evaluated the substrate specificities of four proline cis-selective hydroxylases toward the efficient synthesis of proline derivatives. In an initial evaluation, 15 proline-related compounds were investigated as substrates. In addition to l-proline and l-pipecolinic acid, we found that 3,4-dehydro-l-proline, l-azetidine-2-carboxylic acid, cis-3-hydroxy-l-proline, and l-thioproline were also oxygenated. Subsequently, the product structures were determined, revealing cis-3,4-epoxy-l-proline, cis-3-hydroxy-l-azetidine-2-carboxylic acid, and 2,3-cis-3,4-cis-3,4-dihydroxy-l-proline.

  我们评估了四种脯氨酸顺式选择性羟化酶对脯氨酸衍生物高效合成的底物特异性。在初步评估中，我们研究了15种脯氨酸相关化合物作为底物。除了l-脯氨酸和l-哌哌酸外，我们发现3,4-去氢脯氨酸、l-吡啶二羧酸、顺式-3-羟基-l-脯氨酸和l-硫脯氨酸也被氧化。随后，确定了产物结构，揭示了顺式-3,4-环氧-l-脯氨酸、顺式-3-羟基-l-吡啶二羧酸和2,3-顺式-3,4-顺式-3,4-二羟基-l-脯氨酸。
• Studies on the selectivity of proline hydroxylases reveal new substrates including bicycles
  作者：Tristan J. Smart、Refaat B. Hamed、Timothy D.W. Claridge、Christopher J. Schofield

  DOI：10.1016/j.bioorg.2019.103386

  日期：2020.1

  Studies on the substrate selectivity of recombinant ferrous-iron- and 2-oxoglutarate-dependent proline hydroxylases (PHs) reveal that they can catalyse the production of dihydroxylated 5-, 6-, and 7-membered ring products, and can accept bicyclic substrates. Ring-substituted substrate analogues (such hydroxylated and fluorinated prolines) are accepted in some cases. The results highlight the considerable

  对依赖于铁-铁和2-氧戊二酸酯的脯氨酸羟化酶重组酶的底物选择性的研究表明，它们可以催化二羟基化的5、6和7元环产物的产生，并且可以接受双环底物。在某些情况下，可以接受环取代的底物类似物（例如羟基化和氟化的脯氨酸）。结果突出了在生物催化中氨基酸羟化酶和其他2OG加氧酶的巨大潜力，但尚未充分开发。
• Modular Chemoenzymatic Synthesis of GE81112 B1 and Related Analogues Enables Elucidation of Its Key Pharmacophores
  作者：Christian R. Zwick、Max B. Sosa、Hans Renata

  DOI：10.1021/jacs.0c13424

  日期：2021.1.27

  initiation. Herein we report the use of a chemoenzymatic strategy to complete the first total synthesis of GE81112 B1. By pairing iron and α-ketoglutarate dependent hydroxylases found in GE81112 biosynthesis with traditional synthetic methodology, we were able to access the natural product in 11 steps (longest linear sequence). Following this strategy, 10 GE81112 B1 analogues were synthesized, allowing for identification

  GE81112 复合物因其广泛的抗菌特性和独特的抑制细菌翻译起始的能力而备受关注。在此，我们报告了使用化学酶促策略完成 GE81112 B1 的首次全合成。通过将 GE81112 生物合成中发现的铁和 α-酮戊二酸依赖性羟化酶与传统合成方法配对，我们能够通过 11 个步骤（最长的线性序列）获得天然产物。遵循这一策略，合成了 10 个 GE81112 B1 类似物，从而确定了其关键药效团。我们药物化学工作的一个关键特征是在模块化类似物合成中加入额外的生物催化羟基化，以快速探索相关的化学空间。
• Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: Application of an organocatalytic direct vinylogous aldol reaction
  作者：Sunil V. Pansare、Eldho K. Paul

  DOI：10.1039/c2ob06644k

  日期：——

  The γ-butenolide obtained from an organocatalyzed, direct vinylogous aldol reaction of γ-crotonolactone and benzaldehyde serves as the key starting material in the expedient synthesis of a 3-hydroxy-2-phenyl piperidine intermediate which is converted to the target 2,3-disubstituted piperidines.

  从γ-克罗通内酯和苯甲醛的有机催化直接维尼洛格斯阿尔多尔反应中获得的γ-丁内酯，作为合成目标2,3-二取代吡啶的关键起始材料，经过高效合成得到3-羟基-2-苯基呱啶中间体。
• Enantioselective Ring Expansion of Prolinols: An Efficient and Short Synthesis of 2-Phenylpiperidin-3-ol Derivatives and 3-Hydroxypipecolic Acids
  作者：Domingo Gomez Pardo、Janine Cossy、Anne Cochi、Benjamin Burger、Cristina Navarro、Yang Zhao、Theodore Cohen

  DOI：10.1055/s-0029-1217568

  日期：2009.8

  A very short route to 2-phenylpiperidin-3-ol derivatives and 3-hydroxypipecolic acids is described. The approach uses two key steps: a one-pot reduction/Grignard addition sequence applied to alkyl proline esters and a ring expansion applied to the corresponding prolinols.

  描述了一种非常简短的方法来合成2-苯基哌啶-3-醇衍生物和3-羟基皮克酸。该方法采用两个关键步骤：针对烷基脯氨酸酯的一锅还原/格氏试剂加成反应序列，以及对相应脯氨醇的环扩展反应。