(S)-(+)-3-羟基丁酸钠盐 | 127604-16-4

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪酸
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: (S)-(+)-3-羟基丁酸钠盐
• 中文别名: (S)-(+)-3-羟丁酸钠
• 英文名称: (S)-3-hydroxybutyric acid sodium salt
• 英文别名: Sodium (S)-3-hydroxybutanoate；sodium;(3S)-3-hydroxybutanoate
• CAS: 127604-16-4
• 化学式: C₄H₇O₃*Na
• 分子量: 126.088
• InChiKey: NBPUSGBJDWCHKC-DFWYDOINSA-M

物化性质

• 熔点：
  149-153 °C(lit.)
• 溶解度：
  乙醇：5mg/mL； PBS（pH 7.2）：10 mg/mL
• 稳定性/保质期：

  如果按照规格使用和储存，不会发生分解，并且没有已知的危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  -4.49
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25,S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2918199090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (S)-(+)-3-羟基丁酸钠盐 在 盐酸 、 氯化亚砜 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  An LC-MS/MS method to quantify acylcarnitine species including isomeric and odd-numbered forms in plasma and tissues

  摘要：

  Acylcarnitines are intermediates of fatty acid and amino acid oxidation found in tissues and body fluids. They are important diagnostic markers for inherited diseases of peroxisomal and mitochondrial oxidation processes and were recently described as biomarkers of complex diseases like the metabolic syndrome. Quantification of acylcarnitine species can become challenging because various species occur as isomers and/or have very low concentrations. Here we describe a new LC-MS/MS method for quantification of 56 acylcarnitine species with acyl-chain lengths from C2 to C18. Our method includes amino acid-derived positional isomers, like methacrylyl-carnitine (2-M-C3:1-CN) and crotonyl-carnitine (C4:1-CN), and odd-numbered carbon species, like pentadecanoyl-carnitine (C15:0-CN) and heptadecanoyl-carnitine (C17:0-CN), occurring at very low concentrations in plasma and tissues. Method validation in plasma and liver samples showed high sensitivity and excellent accuracy and precision. In an application to samples from streptozotocin-treated diabetic mice, we identified significantly increased concentrations of acylcarnitines derived from branched-chain amino acid degradation and of odd-numbered straight-chain species, recently proposed as potential biomarkers for the metabolic syndrome. In conclusion, the LC-MS/MS method presented here allows robust quantification of isomeric acylcarnitine species and extends the palette of acylcarnitines with diagnostic potential derived from fatty acid and amino acid metabolism.

  DOI：

  10.1194/jlr.d061721
• 作为产物：
  描述：

  (S)-3-羟基丁酸甲酯 在 sodium hydroxide 作用下， 生成 (S)-(+)-3-羟基丁酸钠盐
  参考文献：
  名称：

  Tai, Akira; Morimoto, Naotake; Yoshikawa, Masato, Agricultural and Biological Chemistry, 1990, vol. 54, # 7, p. 1753 - 1762

  摘要：

  DOI：

文献信息

• Sythesis of 1,3-dioxin-4-ones and their use in synthesis. XVIII. Synthesis of azetidin-2-ones from 1,3-dioxin-4-ones via 3-hydroxycarboxamides.
  作者：Jun-ichi SAKAKI、Satoshi KOBAYASHI、Masayuki SATO、Chikasra KANEKO

  DOI：10.1248/cpb.37.2952

  日期：——

  A general method for the synthesis of azetidin-2-ones from 1, 3-dioxin-4-ones is described. The method consists of 1) the formatin of β-ketocarboxamides, 2) their reduction to 3-hydroxycarboxamides, 3) mesylationg, and 4) base-mediated cyclization of 3-mesyloxycarboxamides to the final azetidinones. Stereochemical demand in the cyclizatino step has been clarified by using 5, 6-tri- and -tetramethylene derivatives of 2, 2-dimethyl-1, 3-dioxin-4-one. Microbiological reduction of the acetoacetamides by baker's yeast gave (S)-3-hydroxybutanamides of ≥98% optical purity, whose cyclization afforded (R)-4-methylazetidin-2-ones.

  描述了一种从1,3-二氧戊环-4-酮合成氮杂环丁-2-酮的一般方法。该方法包括：1）形成β-酮羧酰胺，2）将其还原为3-羟基羧酰胺，3）甲磺酰化，以及4）3-甲磺酰氧基羧酰胺在碱介导下环化，得到最终的氮杂环丁酮。通过使用2,2-二甲基-1,3-二氧戊环-4-酮的5,6-三甲基和四甲基衍生物，阐明了环化步骤中的立体化学需求。利用面包酵母对乙酰乙酰胺进行微生物还原，得到了光学纯度≥98%的(S)-3-羟基丁酰胺，其环化产物为(R)-4-甲基氮杂环丁-2-酮。
• Synthesis and studies of catechol-containing mycobactin S and T analogs
  作者：Andrew J. Walz、Ute Möllmann、Marvin J. Miller

  DOI：10.1039/b703116e

  日期：——

  The syntheses of catechol-containing mycobactin S and T analogs are described. These analogs incorporate a catechol-glycine moiety in place of the phenol-oxazoline of the naturally occurring mycobactins S and T. Studies indicated that the new siderophore analogs bind iron, and promote the growth of a number of microbes, especially strains of mycobacteria, as expected.

  描述了含邻苯二酚的霉菌素S和T类似物的合成。这些类似物取代了天然分枝杆菌素S和T的苯酚-恶唑啉，取代了儿茶酚-甘氨酸部分。研究表明，新的铁载体类似物结合铁，并促进许多微生物（尤其是分枝杆菌菌株）的生长，例如预期的。
• β-Lactams in synthesis: short syntheses of cobactin analogs
  作者：Andrew J. Walz、Marvin J. Miller

  DOI：10.1016/j.tetlet.2007.05.085

  日期：2007.7

  Mycobactins facilitate assimilation of iron by mycobacteria. Synthetic analogs with structural variation of the cobactin component have potent anti-TB activity. A new method for the synthesis of cobactin analogs is presented. The key process involves single-step coupling reactions between an amine of a cyclic (l)-lysine derived hydroxamic acid with cyanide activated β-lactams.

  分支杆菌素促进分枝杆菌对铁的吸收。具有烟草素成分结构变化的合成类似物具有有效的抗结核病活性。提出了一种新的合成cobactin类似物的方法。关键过程涉及环状（l）-赖氨酸衍生的异羟肟酸的胺与氰化物活化的β-内酰胺之间的单步偶联反应。
• 一种(R)-3-羟基丁酸-(R)-羟基丁酯及其中间体的合成方法和应用
  申请人：上海远志昌浦生物科技有限公司

  公开号：CN114957004A

  公开（公告）日：2022-08-30

  本发明公开了一种(R)‑3‑羟基丁酸‑(R)‑羟基丁酯及其中间体的合成方法和应用，涉及医药化学领域。本发明以(R)‑3‑羟基丁酸钠和(R)‑3‑羟基丁酸乙酯为原料，提供了一种安全可控，生产成本低，纯度高，环境友好，适合工业化生产(R)‑3‑羟基丁酸‑(R)‑羟基丁酯的方法，且合成效率高，产品纯度达到98.0％以上。
• Unexpected Preference of the <i>E. coli</i> Translation System for the Ester Bond during Incorporation of Backbone-Elongated Substrates
  作者：Shinsuke Sando、Kenji Abe、Nobuhiko Sato、Toshihiro Shibata、Keigo Mizusawa、Yasuhiro Aoyama

  DOI：10.1021/ja068033n

  日期：2007.5.1

  There have been recent advances in the ribosomal synthesis of various molecules composed of nonnatural ribosomal substrates. However, the ribosome has strict limitations on substrates with elongated backbones. Here, we show an unexpected loophole in the E. coli translation system, based on a remarkable disparity in its selectivity for beta-amino/hydroxy acids. We challenged beta-hydroxypropionic acid (beta-HPA), which is less nucleophilic than beta-amino acids but free from protonation, to produce a new repertoire of ribosome-compatible but main-chain-elongated substrates. PAGE analysis and mass-coupled S-tag assays of amber suppression experiments using yeast suppressor tRNA(CUA)(Phe) confirmed the actual incorporation of beta-HPA into proteins/oligopeptides. We investigated the side-chain effects of beta-HPA and found that the side chain at position alpha and R stereochemistry of the beta-substrate is preferred and even notably enhances the efficiency of incorporation as compared to the parent substrate. These results indicate that the E. coli translation machinery can utilize main-chain-elongated substrates if the pK(a) of the substrate is appropriately chosen.