allyl 2,4-di-O-benzoyl-α-L-fucopyranoside | 286476-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,4-di-O-benzoyl-α-L-fucopyranoside
• 英文别名: allyl 2,4-di-O-benzoyl-alpha-l-fucopyranoside；[(2S,3S,4R,5S,6R)-5-benzoyloxy-4-hydroxy-2-methyl-6-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 286476-62-8
• 化学式: C₂₃H₂₄O₇
• 分子量: 412.439
• InChiKey: SMUZDUIELUJCKR-IDVLOGFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 2,4-di-O-benzoyl-α-L-fucopyranoside 在 吗啉 、 吡啶 、 四(三苯基膦)钯 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.67h， 生成 allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis and conjugation of a sulfated disaccharide involved in the aggregation process of the marine sponge Microciona prolifera

  摘要：

  The synthesis is reported of allyl (sodium 2-acetamido-2-deoxy-beta-D-glucopyranosyl 3-sulfate)-(1-->3)-alpha-L-fucopyranoside which represents an oligosaccharide fragment of the aggregation factor of the marine sponge Microciona prolifera. The title compound was obtained by coupling of 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with allyl 2,4-di-O-benzoyl-alpha-Lfucopyranoside, followed by de-isopropylidenation, acetylation, de-allyloxycarbonylation, sulfation, de-acylation, and finally N-acetylation. The allyl glycoside was eventually converted into a 3-(2-aminoethylthio)propyl glycoside and then coupled to bovine serum albumin (BSA) using diethyl squarate as the bivalent linker, yielding 8 hapten molecules per molecule of BSA. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00585-6
• 作为产物：
  描述：

  allyl 2-O-benzoyl-3,4-O-isopropylidene-α-L-fucopyranoside 在 对甲苯磺酸 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.75h， 生成 allyl 2,4-di-O-benzoyl-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis and conjugation of a sulfated disaccharide involved in the aggregation process of the marine sponge Microciona prolifera

  摘要：

  The synthesis is reported of allyl (sodium 2-acetamido-2-deoxy-beta-D-glucopyranosyl 3-sulfate)-(1-->3)-alpha-L-fucopyranoside which represents an oligosaccharide fragment of the aggregation factor of the marine sponge Microciona prolifera. The title compound was obtained by coupling of 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with allyl 2,4-di-O-benzoyl-alpha-Lfucopyranoside, followed by de-isopropylidenation, acetylation, de-allyloxycarbonylation, sulfation, de-acylation, and finally N-acetylation. The allyl glycoside was eventually converted into a 3-(2-aminoethylthio)propyl glycoside and then coupled to bovine serum albumin (BSA) using diethyl squarate as the bivalent linker, yielding 8 hapten molecules per molecule of BSA. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00585-6

文献信息

• Synthesis of Gold Glyconanoparticles: Possible Probes for the Exploration of Carbohydrate-Mediated Self-Recognition of Marine Sponge Cells
  作者：Adriana�Carvalho� de Souza、Koen�M. Halkes、Johannes�D. Meeldijk、Arie�J. Verkleij、Johannes�F.�G. Vliegenthart、Johannis�P. Kamerling

  DOI：10.1002/ejoc.200400255

  日期：2004.11

  step in marine sponge cell recognition and adhesion operates via a calcium-dependent proteoglycan− proteoglycan interaction. For the marine sponge Microciona prolifera, one of the carbohydrate epitopes involved in the proteoglycan self-recognition is a sulfated disaccharide [GlcpNAc3S(β1−3)Fucp]. Earlier surface plasmon resonance studies have demonstrated that the proteoglycan self-recognition can be

  海洋海绵细胞识别和粘附的第一步是通过钙依赖性蛋白多糖-蛋白多糖相互作用进行的。对于海洋海绵 Microciona prolifera，参与蛋白多糖自我识别的碳水化合物表位之一是硫酸化二糖 [GlcpNAc3S(β1−3)Fucp]。早期的表面等离子体共振研究表明，当通过与牛血清白蛋白结合多价呈现时，可以用合成的 β-D-GlcpNAc-(13)-α-L-Fucp-(1O) 模拟蛋白多糖的自我识别。在这里，直接合成涂有糖苷 β-D-GlcpNAc3S-(13)-α-L-Fucp-(1O)(CH2)3S(CH2)6SH、β-D-GlcpNAc3S-( 13)-β-L-Fucp-(1O)(CH2)3S(CH2)6SH, β-D-GlcpNAc3S-(1O)(CH2)3S(CH2)6SH, α-L-Fucp-(1O)(CH2 )3S(CH2)6SH, β-D-Glcp-NAc3S-(13)-α-L
• Gold nanoparticles coated with a pyruvated trisaccharide epitope of the extracellular proteoglycan of Microciona prolifera as potential tools to explore carbohydrate-mediated cell recognition
  作者：Adriana Carvalho de Souza、Johannes F. G. Vliegenthart、Johannis P. Kamerling

  DOI：10.1039/b802235f

  日期：——

  the proteoglycan-proteoglycan self-recognition, beta-d-Galp4,6(R)Pyr-(1-->4)-beta-d-GlcpNAc-(1-->3)-alpha-l-Fucp-(1-->O)(CH(2))(3 )S(CH(2))(6)SH was synthesized, and partially converted into gold glyconanoparticles. These mimics are being used to explore the self-interaction phenomenon for the trisaccharide epitope, via TEM aggregation experiments (gold glyconanoparticles) and atomic force microscopy

  海洋海绵Microciona prolifera中物种特异性的细胞粘附涉及细胞外蛋白聚糖样大分子复合物（也称为聚集因子）的相互作用。在相互作用中，两个高度多价的功能域发挥作用：细胞结合域和自我相互作用域。自我识别已被表征为重复低亲和力碳水化合物表位的Ca（2+）依赖性碳水化合物相互作用。涉及的表位之一是丙酮酸三糖β-d-Galp4,6（R）Pyr-（1→4）-β-d-GlcpNAc-（1→3）-1-Fucp。为了评估这种三糖在蛋白聚糖-蛋白聚糖自我识别中的作用，β-d-Galp4,6（R）Pyr-（1-> 4）-beta-d-GlcpNAc-（1-> 3）-合成了α-1-Fucp-（1-> O）（CH（2））（3）S（CH（2））（6）SH，并部分转化为金纳米颗粒。这些模拟物被用于通过TEM聚集实验（金纳米颗粒）和原子力显微镜（AFM）实验（自组装单层；结合力）来探索三糖表位的自相互作用现象。
• Xue, Jun; Khaja, Sirajud D.; Locke, Robert D., Synlett, 2004, # 5, p. 861 - 865
  作者：Xue, Jun、Khaja, Sirajud D.、Locke, Robert D.、Matta, Khushi L.

  DOI：——

  日期：——
• Synthesis and conjugation of a sulfated disaccharide involved in the aggregation process of the marine sponge Microciona prolifera
  作者：Henricus J. Vermeer、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/s0957-4166(99)00585-6

  日期：2000.2

  The synthesis is reported of allyl (sodium 2-acetamido-2-deoxy-beta-D-glucopyranosyl 3-sulfate)-(1-->3)-alpha-L-fucopyranoside which represents an oligosaccharide fragment of the aggregation factor of the marine sponge Microciona prolifera. The title compound was obtained by coupling of 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with allyl 2,4-di-O-benzoyl-alpha-Lfucopyranoside, followed by de-isopropylidenation, acetylation, de-allyloxycarbonylation, sulfation, de-acylation, and finally N-acetylation. The allyl glycoside was eventually converted into a 3-(2-aminoethylthio)propyl glycoside and then coupled to bovine serum albumin (BSA) using diethyl squarate as the bivalent linker, yielding 8 hapten molecules per molecule of BSA. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Model System for Cell Adhesion Mediated by Weak Carbohydrate–Carbohydrate Interactions
  作者：Bärbel Lorenz、Luis Álvarez de Cienfuegos、Marieelen Oelkers、Ella Kriemen、Christian Brand、Milena Stephan、Eva Sunnick、Deniz Yüksel、Venkateshwarlu Kalsani、Krishna Kumar、Daniel B. Werz、Andreas Janshoff

  DOI：10.1021/ja210304j

  日期：2012.2.22

  The multivalent carbohydrate-carbohydrate interaction between membrane-anchored epitopes derived from the marine sponge Microciona prolifera has been explored by colloidal probe microscopy. An in situ coupling of sulfated and non-sulfated disaccharides to membrane-coated surfaces was employed to mimic native cell cell contacts. The dynamic strength of the homomeric self-association was measured as a function of calcium ions and loading rate. A deterministic model was used to estimate the basic energy landscape and number of participating bonds in the contact zone.