(S)-methyl 3-hydroxy-4-((4-methoxybenzyl)oxy)-2-methylenebutanoate | 1222854-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-methyl 3-hydroxy-4-((4-methoxybenzyl)oxy)-2-methylenebutanoate
• 英文别名: methyl (S)-3-hydroxy-4-(p-methoxybenzyloxy)-2-methylenebutanoate；methyl (3S)-3-hydroxy-4-[(4-methoxyphenyl)methoxy]-2-methylidenebutanoate
• CAS: 1222854-19-4
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: GKJCHBMNFYXRIQ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-methyl 3-hydroxy-4-((4-methoxybenzyl)oxy)-2-methylenebutanoate 在 lithium hydroxide monohydrate 、 camphor-10-sulfonic acid 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 (4’S,1’’S)-1’’-(p-tolyl)but-3’’-en-1’’-yl 2-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)propenoate
  参考文献：
  名称：

  A New Template of MIitsunobu Acylate Cleavable in Non-Alkaline Conditions

  摘要：

  DOI：

  10.3987/com-21-14562
• 作为产物：
  描述：

  4-(((4-methoxybenzyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane 在 盐酸 、 sodium periodate 、 L-(+)-酒石酸二异丙酯 、 titanium(IV)isopropoxide 、 奎宁环-3-醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 185.0h， 生成 (S)-methyl 3-hydroxy-4-((4-methoxybenzyl)oxy)-2-methylenebutanoate
  参考文献：
  名称：

  郁金香脂质体转化酶的底物特异性，郁金香中独特的非酯水解性羧酸酯酶：底物醇部分对酶活性的影响。

  摘要：

  6-Tuliposides A（PosA）和B（PosB）是作为主要防御性次要代谢产物积聚在郁金香（Tulipa gesneriana）中的葡萄糖酯。我们先前从郁金香中发现的Pos转换酶（TgTCEs）分别催化PosA和PosB分别转化为抗菌性郁金香脂蛋白A（PaA）和B（PaB）的反应。属于羧酸酯酶家族的TgTCEs特异性催化分子内酯交换反应，但不催化水解。在本报告中，我们合成了具有各种醇基的Pos类似物，并测量了TgTCE活性，并确定了这些类似物的动力学参数，以期探索独特的非酯水解TgTCEs的底物识别机制。已经发现，d-葡萄糖样结构和醇部分中羟基的数目对于TgTCE识别底物很重要。在检测的类似物中，发现通过降低Km值，TgTCE比真实的底物更能特异性地识别PosA和PosB的1,2-二脱氧类似物。本结果将为设计用于TgTCE晶体学分析的简单，稳定的合成底物类似物提供基础。

  DOI：

  10.1016/j.bmcl.2018.12.010

文献信息

• Asymmetric Total Synthesis of 6-Tuliposide B and Its Biological Activities against Tulip Pathogenic Fungi
  作者：Kengo SHIGETOMI、Shoko OMOTO、Yasuo KATO、Makoto UBUKATA

  DOI：10.1271/bbb.100845

  日期：2011.4.23

  The structure-activity relationship was investigated to evaluate the antifungal activities of tuliposides and tulipalins against tulip pathogenic fungi. 6-Tuliposide B was effectively synthesized via the asymmetric Baylis-Hillman reaction. Tuliposides and tulipalins showed antifungal activities against most of the strains tested at high concentrations (2.5 mm), while Botrytis tulipae was resistant to tuliposides. Tulipalin formation was involved in the antifungal activity, tulipalin A showed higher inhibitory activity than 6-tuliposide B and tulipalin B. Both the tuliposides and tulipalins showed pigment-inducing activity against Gibberella zeae and inhibitory activity against Fusarium oxysporum f. sp tulipae. These activities were induced at a much lower concentration (0.05 mm) than the antifungal MIC values.

  为评估郁金香苷和郁金香醛对郁金香致病真菌的抗真菌活性，研究了其结构-活性关系。通过不对称 Baylis-Hillman 反应，有效合成了 6-郁金香苷 B。郁金香苷和郁金香醛在高浓度（2.5 毫米）下对大多数受试菌株具有抗真菌活性，而郁金香灰霉病菌对郁金香苷具有抗性。郁金香苷的形成参与了抗真菌活性，郁金香苷 A 的抑制活性高于 6-郁金香苷 B 和郁金香苷 B。郁金香苷和郁金香醛都对 Gibberella zeae 具有色素诱导活性，对 Fusarium oxysporum f. sp tulipae 具有抑制活性。这些活性是在比抗真菌 MIC 值低得多的浓度（0.05 毫米）下产生的。
• The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure–activity relationship
  作者：Kengo Shigetomi、Kazuaki Shoji、Shinya Mitsuhashi、Makoto Ubukata

  DOI：10.1016/j.phytochem.2009.10.008

  日期：2010.2

  6-Tuliposide B is a secondary metabolite occurring specifically in tulip anthers. Recently, a potent antibacterial activity of 6-tuliposide B has been reported. However, its molecular target has not yet been established, nor its action mechanism. To shed light on such issues, 6-tuliposide B and tulipalin B analogues were synthesized and a structure-activity relationship (SAR) was examined using a broad panel of bacterial strains. As the results of SAR among a total of 25 compounds, only tulipalin B and the compounds having 3',4'-dihydroxy-2'-methylenebutanoate (DHMB) moieties showed any significant antibacterial activity. Moreover, the 3'R analogues of these compounds displayed essentially the same activities as 6-tuliposide B and the structure of the 3'R-DMBA moiety was the same as that of the proposed active moiety of cnicin. These results suggest that 6-tuliposide B has the same action mechanism as proposed for cnicin and bacteria) MurA is one of the major molecular targets of 6-tuliposide B. (C) 2009 Elsevier Ltd. All rights reserved.