(S)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-1,3-dioxolane | 109786-73-4

• 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)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-1,3-dioxolane
• 英文别名: (S)-(+)-4-(4-methoxybenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane；(4S)-4-[(4-methoxyphenyl)methoxymethyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 109786-73-4
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: BPKYSNQMGKMWGC-ZDUSSCGKSA-N

物化性质

• 沸点：
  341.6±32.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-1,3-dioxolane 在 silica gel 作用下， 以3.6 g的产率得到(R)-3-(4-methoxybenzyloxy)propane-1,2-diol
  参考文献：
  名称：

  具有磷脂和多不饱和脂肪酸的生物共轭酯类萜的合成。

  摘要：

  已经合成了一系列具有磷脂和多不饱和脂肪酸（PUFA）的酯类生物共轭物，用于在几种癌细胞系中作为抗增殖剂进行生物活性测试。通过改变甘油中1或2位上的酯类萜或磷酸胆碱或PUFA单元中的酯类萜类化合物，获得了原始脂质醚edefosine（1-O-十八烷基-2-O-甲基-rac-glycero-3-磷酸胆碱）的不同取代类似物。位置3。还获得了简单的酯类生物类化合物与二十碳五烯酸（EPA）的生物共轭物。所有合成衍生物均针对人肿瘤细胞HeLa（子宫颈）和MCF-7（乳腺癌）进行了测试。一些化合物对这些细胞系显示出良好的IC50（0.3和0.2μM）值。

  DOI：

  10.3390/molecules21010047
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 乙醇 、 乙酸乙酯 、 乙腈 为溶剂， 反应 5.0h， 生成 (S)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of Modified Peptidoglycan Precursor Analogues for the Inhibition of Glycosyltransferase

  摘要：

  The peptidoglycan glycosyltransferases (GTs) are essential enzymes that catalyze the polymerization of On OH glycan chains of the bacterial cell wall from lipid II and thus constitute a validated antibacterial target. Their enzymatic cavity is composed of a donor site for the growing glycan chain (where the inhibitor moenomycin binds) and an acceptor site for lipid II substrate. In order to find lead inhibitors able to fill this large active site, we have synthesized a series of substrate analogues of lipid I and lipid II with variations in the lipid, the pyrophosphate, and the peptide moieties and evaluated their biological effect on the GT activity of E. coli PBP1b and their antibacterial potential. We found several compounds able to inhibit the GT activity in vitro and cause growth defect in Bacillus subtilis. The more active was C16-phosphoglycerate-MurNAc-(L-Alao-D-Glu)-GIcNAc, which also showed antibacterial activity. These molecules are promising leads for the design of new antibacterial GT inhibitors.

  DOI：

  10.1021/ja302099u

文献信息

• Total Synthesis of the Congested, Bisphosphorylated <i>Morganella morganii</i> Zwitterionic Trisaccharide Repeating Unit
  作者：D. Jamin Keith、Steven D. Townsend

  DOI：10.1021/jacs.9b06830

  日期：2019.8.14

  Zwitterionic polysaccharides (ZPS) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis--glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β(1→3)-GalNAc;

  两性离子多糖 (ZPS) 通过主要组织相容性复合体 II 类呈递激活 T 细胞依赖性免疫反应。在此，我们报告了摩根氏菌 ZPS 重复单元的首次合成，作为合成新型 ZPS 材料的有利工具。重复单元包含一个 1,2-顺式-α-糖苷键；有问题的 1,2-反式半乳糖苷键，Gal-β(1→3)-GalNAc；和磷酸甘油和磷酸胆碱残基，它们以前没有被观察到作为同一寡糖上的官能团。成功的第三代方法利用了磷酸甘油功能化受体的一流糖基化。为了安装磷酸胆碱单元，合成了一种高效的磷酸胆碱供体。
• Synthetic Study on Lipoteichoic Acid of Gram Positive Bacteria. I. Synthesis of Proposed Fundamental Structure of<i>Streptococcus pyogenes</i>Lipoteichoic Acid
  作者：Koichi Fukase、Takahiro Matsumoto、Naoko Ito、Takuya Yoshimura、Shozo Kotani、Shoichi Kusumoto

  DOI：10.1246/bcsj.65.2643

  日期：1992.10

  Synthetic study on Streptococcus pyogenes lipoteichoic acid (LTA) which was reported to induce nontoxic TNF is described. The proposed fundamental structure of LTA was constructed by coupling of the glycolipid part with the poly(glycerol phosphate) (PGP) part and subsequent deprotection. The PGP part was prepared by a simple repeating procedure using the phosphoramidite method for the construction

  描述了对据报道可诱导无毒 TNF 的化脓性链球菌脂磷壁酸 (LTA) 的合成研究。LTA 的基本结构是通过将糖脂部分与聚（甘油磷酸）（PGP）部分偶联并随后去保护来构建的。PGP 部分是通过简单的重复程序制备的，使用亚磷酰胺方法构建 1,3-磷酸二酯键。糖脂部分是使用适当的糖基氟作为供体合成的，其中对硝基苄基成功地用于临时保护羟基官能团。
• Compound comprising a fluorine-substituted alkyl group and a liposome contrast medium comprising the compound
  申请人：FUJIFILM Corporation

  公开号：EP1916255A3

  公开（公告）日：2012-08-22

  A steroid ester compound of a terminally-fluorinated alkyl fatty acid, a steroid compound having bis(trifluoromethyl)phenyl group, a phosphatidylserine compound having a terminally-fluorinated alkyl group, a glyceride compound having bis(trifluoromethyl phenyl group, or a glyceride compound having a terminally-fluorinated alkyl group. A vascular lesion can be selectively imaged by using a contrast medium comprising a liposome containing said compound or a salt thereof.

  一种具有终端氟化烷基脂肪酸的类固醇酯化合物，一种具有双(三氟甲基)苯基的类固醇化合物，一种具有终端氟化烷基团的磷脂酰丝氨酸化合物，一种具有双(三氟甲基苯基的甘油酯化合物，或一种具有终端氟化烷基团的甘油酯化合物。通过使用含有该化合物或其盐的脂质体的造影剂，可以选择性地成像血管病变。
• Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes
  作者：Stuart J. Conway、James Gardiner、Simon J. A. Grove、Melloney K. Johns、Ze-Yi Lim、Gavin F. Painter、Diane E. J. E. Robinson、Christine Schieber、Jan W. Thuring、Leon S.-M. Wong、Meng-Xin Yin、Antony W. Burgess、Bruno Catimel、Phillip T. Hawkins、Nicholas T. Ktistakis、Leonard R. Stephens、Andrew B. Holmes

  DOI：10.1039/b913399b

  日期：——

  The synthesis of the complete family of phosphatidylinositol phosphate analogues (PIPs) from five key core intermediates A–E is described. These core compounds were obtained from myo-inositol orthoformate 1via regioselective DIBAL-H and trimethylaluminium-mediated cleavages and a resolution–protection process using camphor acetals 10. Coupling of cores A–E with phosphoramidites 34 and 38, derived from the requisite protected lipid side chains, afforded the fully-protected PIPs. Removal of the remaining protecting groups was achieved via hydrogenolysis using palladium black or palladium hydroxide on carbon in the presence of sodium bicarbonate to afford the complete family of dipalmitoyl- and amino-PIP analogues 42, 45, 50, 51, 58, 59, 67, 68, 76, 77, 82, 83, 92, 93, 99 and 100. Investigations using affinity probes incorporating these compounds have identified novel proteins involved in the PI3K intracellular signalling network and have allowed a comprehensive proteomic analysis of phosphoinositide interacting proteins.

  报道了从五个关键的核心中间体A-E合成完整的磷脂酰肌醇磷酸类似物（PIPs）家族的方法。这些核心化合物通过选择性DIBAL-H和三甲基铝介导的裂解以及使用樟脑乙缩醛的解析保护过程，从肌醇原甲酸1中获得。将核心A-E与从所需保护的脂质侧链衍生的磷酰胺34和38偶联，得到了完全保护的PIPs。通过使用钯黑或碳上的钯氢氧化物在碳酸氢钠存在下的氢解，去除了剩余的保护基团，得到了完整的二棕榈酰和氨基PIP类似物42、45、50、51、58、59、67、68、76、77、82、83、92、93、99和100。利用包含这些化合物的亲和探针进行的研究，鉴定了参与PI3K细胞内信号网络的新蛋白，并允许对磷脂酰肌醇相互作用蛋白进行全面的蛋白质组学分析。
• New fluorescent probes reveal that flippase-mediated flip-flop of phosphatidylinositol across the endoplasmic reticulum membrane does not depend on the stereochemistry of the lipid
  作者：Ram A. Vishwakarma、Stefanie Vehring、Anuradha Mehta、Archana Sinha、Thomas Pomorski、Andreas Herrmann、Anant K. Menon

  DOI：10.1039/b500300h

  日期：——

  Glycerophospholipid flip-flop across biogenic membranes such as the endoplasmic reticulum (ER) is a fundamental feature of membrane biogenesis. Flip-flop requires the activity of specific membrane proteins called flippases. These proteins have yet to be identified in biogenic membranes and the molecular basis of their action is unknown. It is generally believed that flippase-facilitated glycerophospholipid flip-flop across the ER is governed by the stereochemistry of the glycerolipid, but this important issue has not been resolved. Here we investigate whether the ER flippase stereochemically recognizes the glycerophospholipids that it transports. To address this question we selected phosphatidylinositol (PI), a biologically important molecule with chiral centres in both its myo-inositol headgroup and its glycerol–lipid tail. The flip-flop of PI across the ER has not been previously reported. We synthesized fluorescence-labeled forms of all four diastereoisomers of PI and evaluated their flipping in rat liver ER vesicles, as well as in flippase-containing proteoliposomes reconstituted from a detergent extract of ER. Our results show that the flippase is able to translocate all four PI isomers and that both glycerol isomers of PI flip-flop across the ER membrane at rates similar to that measured for fluorescence-labeled phosphatidylcholine. Our data have important implications for recent hypotheses concerning the evolution of distinct homochiral glycerophospholipid membranes during the speciation of archaea and bacteria/eukarya from a common cellular ancestor.

  甘油磷脂在生物膜（如内质网）上的翻转是膜生物发生的一个基本特征。翻转需要特定膜蛋白（即翻转酶）的活性，但这些蛋白质在生物膜中的身份尚未确定，其作用的分子基础也还不清楚。一般认为，内质网上的翻转酶介导的甘油磷脂翻转受甘油磷脂的手性化学支配，但这一重要问题尚未解决。在此，我们研究内质网翻转酶是否手性识别其转运的甘油磷脂。为解答这一问题，我们选择了磷脂酰肌醇，这种生物学上重要的分子在其肌醇头基和甘油脂尾上都具有手性中心。之前并未有过关于磷脂酰肌醇在内质网翻转的报道。我们合成了所有四种磷脂酰肌醇的非对映异构体并进行荧光标记，评估它们在大鼠肝脏内质网囊泡及从内质网洗涤剂提取物重建的含翻转酶的蛋白脂质体中的翻转情况。结果显示，翻转酶能够转运所有的磷脂酰肌醇异构体，两种磷脂酰肌醇的甘油异构体在内质网膜上的翻转速率与荧光标记的磷脂酰胆碱相当。这些数据对近期有关古菌和细菌/真核生物从共同的细胞祖先演化出不同手性的甘油磷脂膜的假设有着重要意义。