4-(diethoxy-phosphoryl)-2-methyl-but-2-enoic acid methyl ester | 20350-54-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-(diethoxy-phosphoryl)-2-methyl-but-2-enoic acid methyl ester
• 英文别名: Methyl 4-(diethoxyphosphoryl)-2-methylbut-2-enoate；methyl 4-diethoxyphosphoryl-2-methylbut-2-enoate
• CAS: 20350-54-3
• 化学式: C₁₀H₁₉O₅P
• 分子量: 250.232
• InChiKey: MZYRVVXYNBZDDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(diethoxy-phosphoryl)-2-methyl-but-2-enoic acid methyl ester 在 lithium aluminium tetrahydride 、 正丁基锂 、 四溴化碳 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 41.5h， 生成 16-bromo-2,6,10,14-tetramethyl-hexadeca-2,4,6,8,10,14-hexaene
  参考文献：
  名称：

  Didehydrogeranylgeranyl (ΔΔGG):  A Fluorescent Probe for Protein Prenylation

  摘要：

  The first intrinsically fluorescent analog of geranylgeraniol, (2E,6E,8E,10E,12E,14E)-geranylgeraniol (all-trans-DeltaDeltaGGOH.1) has been synthesized stereoselectively and shown to substitute for the geranylgeranyl (GG) moiety in prenyl transferase reactions and in protein-ligand binding assays. All-trans-DeltaDeltaGGOH 1 showed blue fluorescence in methanol, with lambdaex = 310 nm and lambdaem = 410 nm (epsilon310 = 2.4 x 104 M-1 cm-1), but was only weakly fluorescent in aqueous solution. The prenyl transferase efficiency for DeltaDeltaGGPP 2 as a substrate for yeast protein geranylgeranyl transferase (PGGTase-I) was 60% relative to that for GGPP. The binding of DeltaDeltaGG-AcCysMe 3 to the recombinant Rho GTPase dissociation inhibitor (RhoGDI) had a KD of 15.1 +/- 1.2 muM, 6-fold lower than the affinity of GG-AcCysMe. Thus, the DeltaDeltaGG moiety is a novel fluorophore suitable for studying the interaction and subcellular localization of prenylated small GTPase proteins in signaling complexes.

  DOI：

  10.1021/ja0119144
• 作为产物：
  描述：

  惕格酸 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 以 四氯化碳 为溶剂， 反应 49.0h， 生成 4-(diethoxy-phosphoryl)-2-methyl-but-2-enoic acid methyl ester
  参考文献：
  名称：

  Didehydrogeranylgeranyl (ΔΔGG):  A Fluorescent Probe for Protein Prenylation

  摘要：

  The first intrinsically fluorescent analog of geranylgeraniol, (2E,6E,8E,10E,12E,14E)-geranylgeraniol (all-trans-DeltaDeltaGGOH.1) has been synthesized stereoselectively and shown to substitute for the geranylgeranyl (GG) moiety in prenyl transferase reactions and in protein-ligand binding assays. All-trans-DeltaDeltaGGOH 1 showed blue fluorescence in methanol, with lambdaex = 310 nm and lambdaem = 410 nm (epsilon310 = 2.4 x 104 M-1 cm-1), but was only weakly fluorescent in aqueous solution. The prenyl transferase efficiency for DeltaDeltaGGPP 2 as a substrate for yeast protein geranylgeranyl transferase (PGGTase-I) was 60% relative to that for GGPP. The binding of DeltaDeltaGG-AcCysMe 3 to the recombinant Rho GTPase dissociation inhibitor (RhoGDI) had a KD of 15.1 +/- 1.2 muM, 6-fold lower than the affinity of GG-AcCysMe. Thus, the DeltaDeltaGG moiety is a novel fluorophore suitable for studying the interaction and subcellular localization of prenylated small GTPase proteins in signaling complexes.

  DOI：

  10.1021/ja0119144

文献信息

• 一种4-二烃氧基膦酰基-2-甲基-2-丁烯酸烃 基酯的合成方法
  申请人：浙江新和成股份有限公司

  公开号：CN109503657B

  公开（公告）日：2021-03-02

  本发明公开了一种4‑二烃氧基膦酰基‑2‑甲基‑2‑丁烯酸烃基酯的合成方法。本发明在气体保护以及催化剂存在条件下，将2‑甲基‑2‑羟基‑3‑丁烯酸烃基酯(I)与亚磷酸三烃基酯混合，加热反应制得4‑二烃氧基膦酰基‑2‑甲基‑2‑丁烯酸烃基酯。本发明使用的原料易得，价格低廉，具有反应步骤少而且收率高，废弃物排放量少而且容易处理，易于实现工业化的优点。
• Total Synthesis of Nannocystin Ax
  作者：Caroline Poock、Markus Kalesse

  DOI：10.1021/acs.orglett.7b02112

  日期：2017.9.1

  The total synthesis of nannocystin Ax in an overall yield of 11% with 14 steps as the longest linear sequence is reported. Nannocystin Ax is a cytotoxic 21-membered depsipeptide and was isolated from the myxobacterial genus Nannocystis sp. The synthesis uses a vinylogous Horner–Wadsworth–Emmons reaction (HWE) and a vinylogous Mukaiyama aldol reaction (VMAR) as the key steps for the construction of

  据报道，以最长的线性序列为例，以14步的总产率合成了11％的总囊藻毒素Ax。Nannocystin Ax是一种具有细胞毒性的21元depsipeptide，是从粘细菌Nannancystis sp。分离出来的。合成使用乙烯基霍纳-沃兹沃斯-埃蒙斯反应（HWE）和乙烯基Mukaiyama醛醇缩合反应（VMAR）作为构建聚酮化合物片段的关键步骤。大环通过使用COMU的大内酰胺化反应而封闭。
• 4-(二乙氧基-磷酰基)-2-甲基-丁-2-烯酸酯的制备方法
  申请人：上虞新和成生物化工有限公司

  公开号：CN110655533B

  公开（公告）日：2022-05-06

  本发明公开了一种4‑(二乙氧基‑磷酰基)‑2‑甲基‑丁‑2‑烯酸酯的制备方法，包括以下步骤：(a)丙酮醛水溶液通过氧化反应得到丙酮酸/丙酮酸盐水溶液；(b)丙酮酸/丙酮酸盐水溶液与亚乙基二磷酸四乙酯反应后再和醇进行酯化反应得到4‑(二乙氧基‑磷酰基)‑2‑甲基‑丁‑2‑烯酸酯该方法所用的原料便宜易得，各个步骤操作简单，整个路线的收率较高，具有较高的工业应用价值。
• Didehydrogeranylgeranyl (ΔΔGG):  A Fluorescent Probe for Protein Prenylation
  作者：Xiao-hui Liu、Glenn D. Prestwich

  DOI：10.1021/ja0119144

  日期：2002.1.1

  The first intrinsically fluorescent analog of geranylgeraniol, (2E,6E,8E,10E,12E,14E)-geranylgeraniol (all-trans-DeltaDeltaGGOH.1) has been synthesized stereoselectively and shown to substitute for the geranylgeranyl (GG) moiety in prenyl transferase reactions and in protein-ligand binding assays. All-trans-DeltaDeltaGGOH 1 showed blue fluorescence in methanol, with lambdaex = 310 nm and lambdaem = 410 nm (epsilon310 = 2.4 x 104 M-1 cm-1), but was only weakly fluorescent in aqueous solution. The prenyl transferase efficiency for DeltaDeltaGGPP 2 as a substrate for yeast protein geranylgeranyl transferase (PGGTase-I) was 60% relative to that for GGPP. The binding of DeltaDeltaGG-AcCysMe 3 to the recombinant Rho GTPase dissociation inhibitor (RhoGDI) had a KD of 15.1 +/- 1.2 muM, 6-fold lower than the affinity of GG-AcCysMe. Thus, the DeltaDeltaGG moiety is a novel fluorophore suitable for studying the interaction and subcellular localization of prenylated small GTPase proteins in signaling complexes.