Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphanyloxy)-tetrahydro-pyran-4-yl ester | 147072-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphanyloxy)-tetrahydro-pyran-4-yl ester
• CAS: 147072-52-4
• 化学式: C₂₈H₃₄NO₁₁P
• 分子量: 591.552
• InChiKey: OOTPKNMKWABRNQ-JQPIIJRMSA-N

物化性质

• 沸点：
  697.4±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  144.92
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphanyloxy)-tetrahydro-pyran-4-yl ester 在 palladium on activated charcoal 吡啶 、 氢气 、 双氧水 、 环己胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[[[(3R)-3,7-dimethyloct-6-enoxy]-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  P（1）-香茅基-P（2）-α-D-吡喃糖基焦磷酸酯的合成作为大肠杆菌十一碳烯基-焦磷酰基-N-乙酰葡糖胺基转移酶MurG的潜在底物。

  摘要：

  合成了包含α-DN-乙酰基葡糖氨基，α-D-葡糖基和α-DN-乙酰基村mura糖的P（1）-香茅基-P（2）-α-D-吡喃糖基焦磷酸酯，并将其用于大肠杆菌的底物特异性研究MurG酶。与传统的Khorana-Moffatt和二苯基氯代磷酸酯活化策略相比，草酸磷酸酯的草酰氯活化与α-D-吡喃糖-1-磷酸偶联可显着提高产率。

  DOI：

  10.1016/s0960-894x(01)00653-9
• 作为产物：
  描述：

  benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside 在 palladium on activated charcoal 吡啶 、 四氮唑 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphanyloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Identification of a UDP-Gal: GlcNAc-R galactosyltransferase activity in Escherichia coli VW187

  摘要：

  A novel acceptor substrate for galactosyltransferase was synthesized containing GlcNAcalpha-pyrophosphate, covalently bound to a hydrophobic phenoxyundecyl moiety (GlcNAc alpha-PO3-PO3-(CH2)(11)-O-Phenyl). The new substrate was used to develop an assay for a galactosyltransferase activity from Escherichia coli strain VW187 that is involved in lipopolysaccharide synthesis and has not been studied by others. We showed that Gal was transferred from UDP-Gal to the novel acceptor substrate. This was a significant improvement over our previous preliminary assays of the enzyme using endogenous substrate, and showed that these synthetic substrates are useful for assaying enzymes that utilize lipid-bound substrates in O-chain synthesis in Gram-negative bacteria. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.077

文献信息

• Sim, Mui Mui; Kondo, Hirosato; Wong, Chi-Huey, Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2260 - 2267
  作者：Sim, Mui Mui、Kondo, Hirosato、Wong, Chi-Huey

  DOI：——

  日期：——
• Bacterial Surface Engineering Utilizing Glucosamine Phosphate Derivatives as Cell Wall Precursor Surrogates
  作者：Reiko Sadamoto、Takeshi Matsubayashi、Masataka Shimizu、Taichi Ueda、Shuhei Koshida、Toshiaki Koda、Shin-Ichiro Nishimura

  DOI：10.1002/chem.200801734

  日期：2008.11.17
• A very simple synthesis of GlcNAc-α-pyrophosphoryl-decanol: A substrate for the assay of a bacterial galactosyltransferase
  作者：Inka Brockhausen、E. Andreas Larsson、Ole Hindsgaul

  DOI：10.1016/j.bmcl.2007.11.031

  日期：2008.1

  Lipid-linked sugar pyrophosphates, such as GlcNAc-pyrophosphoryl undecaprenol, are important intermediates in the biosynthesis of cell-surface bacterial polysaccharides. It was recently demonstrated that much simpler lipids could substitute for undecaprenol while retaining biological activity, thus making efficient synthetic access to this class of compounds highly desirable. In order to facilitate the synthesis of pure substrates for bacterial glycosyltransferases, we have developed a simple 'two-pot' synthesis which we demonstrate here for GlcNAc-alpha-pyrophosphoryl-decanol (4). GlcNAc pyrophosphate, produced by mild periodate oxidation/beta-elimination of commercial UDP-GlcNAc, is alkylated using 1-iododecane to yield the target compound 4 in 39% yield. Compound 4 is shown to be an efficient acceptor for a bacterial galactosyltransferase. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of Modified Peptidoglycan Precursor Analogues for the Inhibition of Glycosyltransferase
  作者：Shrinivas Dumbre、Adeline Derouaux、Eveline Lescrinier、André Piette、Bernard Joris、Mohammed Terrak、Piet Herdewijn

  DOI：10.1021/ja302099u

  日期：2012.6.6

  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.
• Synthesis of Cell-Permeable <i>N</i>-Acetylhexosamine 1-Phosphates
  作者：Badrinath N. Kakde、Emanuela Capota、Jennifer J. Kohler、Uttam K. Tambar

  DOI：10.1021/acs.joc.1c01781

  日期：2021.12.17