(2S) 3-cyclohexyl-2-O-{1-O-[(1R,2R) 2-O-(α-L-fucopyranosyl)cyclohexyl]β-D-galactopyranos-3-yl}propionic acid | 293752-60-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (2S) 3-cyclohexyl-2-O-{1-O-[(1R,2R) 2-O-(α-L-fucopyranosyl)cyclohexyl]β-D-galactopyranos-3-yl}propionic acid
• 英文别名: CGP-69669A free acid；(2S)-3-cyclohexyl-2-[(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2R)-2-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxycyclohexyl]oxyoxan-4-yl]oxypropanoic acid
• CAS: 293752-60-0
• 化学式: C₂₇H₄₆O₁₃
• 分子量: 578.654
• InChiKey: GNTJIZLFEURZBX-NNIOFZNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  205
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  乙基2,3,4-三-O-苄基-1-硫代-alpha,beta-L-吡喃岩藻糖苷 在 palladium on activated charcoal 甲醇 、 三氟化硼乙醚 、 四丁基溴化铵 、 氢气 、 溴 、 sodium methylate 、 二正丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2S) 3-cyclohexyl-2-O-{1-O-[(1R,2R) 2-O-(α-L-fucopyranosyl)cyclohexyl]β-D-galactopyranos-3-yl}propionic acid
  参考文献：
  名称：

  Ernst, Beat; Dragic, Zorica; Marti, Sébastien, Chimia, 2001, vol. 55, # 4, p. 268 - 274

  摘要：

  DOI：

文献信息

• Substrate specificity of fucosyl transferase III: An efficient synthesis of sialyl Lewis^x-, sialyl Lewis^a-derivatives and mimetics thereof
  作者：Beat Ernst、Bea Wagner、Gabi Baisch、Andreas Katopodis、Tammo Winkler、Reinhold Öhrlein

  DOI：10.1139/v00-081

  日期：2000.6.1

  Fucosyl transferase III (FucT III) has previously been characterized as the most general enzyme of the FucT family, as judged from its ability to catalyze the transfer of fucose to both Galβ(1-3)GlcNAc and Galβ(1-4)GlcNAc. In order to explore the synthetic potential of FucT III for the enzymatic synthesis of sialyl Lewis^xand sialyl Lewis^aderivatives, its substrate specificity has been probed using a number of natural substrate mimetics. A remarkable range of acceptor substrates was found when N-acetyl glucosamine was replaced by D-glucal, (R,R)-1,2-cyclohexanediol and (R,R)-butan-2,3-diol. Although the reaction rates were low compared to the reaction with the natural substrates, they proved to be sufficient for the synthesis of preparative amounts.Key words: fucosyl transferase III, sialyl Lewis^a, sialyl Lewis^x, carbohydrate mimetics.

  Fucosyl转移酶III（FucT III）以其能够催化将岩藻糖转移到Galβ（1-3）GlcNAc和Galβ（1-4）GlcNAc的能力而被认定为FucT家族中最普遍的酶。为了探索FucT III在酶合成唾液酸Lewis x和唾液酸Lewis a衍生物方面的合成潜力，通过使用多种天然底物类似物探测其底物特异性。当N-乙酰葡萄糖胺被D-葡糖醛，（R，R）-1,2-环己二醇和（R，R）-丁烷-2,3-二醇替代时，发现了一系列可接受的底物。尽管与天然底物的反应速率较低，但它们被证明足以合成大量的制备量。关键词：fucosyl转移酶III，唾液酸Lewis a，唾液酸Lewis x，碳水化合物类似物。
• Glycosyltransferases: An Efficient Tool for the Enzymatic Synthesis of Oligosaccharides and Derivatives as well as Mimetics Thereof
  作者：Said Rabbani、Oliver Schwardt、Beat Ernst

  DOI：10.2533/000942906777675047

  日期：——

  Research over the past two decades has uncovered numerous biological roles for carbohydrates, e.g. in cell adhesion processes, signal transduction, malignant transformation, or viral and bacterial cell-surface recognition. Carbohydrates and structural analogues thereof are therefore considered as potential new leads. Although the chemical synthesis of carbohydrates is well established, the preparation of particular oligosaccharides still remains a costly and cumbersome challenge. A complementary approach to the chemical synthesis is the use of enzymatic methods. The transfer of monosaccharide moieties to natural substrates, catalyzed by glycosyltransferases, exhibits excellent chemo-, regio- and stereoselectivity. In addition, enzymatic glycosylations permit the synthesis of carbohydrate derivatives and even carbohydrate mimetics. Our results reveal a remarkable synthetic potential of fucosyltransferases VI (EC 2.4.1.65) and III (EC 2.4.1.65), and ? (2?3)-sialyltransferase ST3Gal III (EC 2.4.99.6). Their use for the preparative synthesis of oligosaccharides and derivatives as well as mimetics thereof is demonstrated.

  过去20年的研究揭示了碳水化合物在许多生物学过程中的作用，例如在细胞黏附过程、信号转导、恶性转化或病毒和细菌细胞表面识别中的作用。因此，碳水化合物及其结构类似物被认为是潜在的新线索。虽然碳水化合物的化学合成已经得到了很好的建立，但特定寡糖的制备仍然是一项昂贵而繁琐的挑战。化学合成的补充方法是使用酶法。由糖基转移酶催化的单糖基团转移到天然底物上，具有出色的化学、区域和立体选择性。此外，酶促糖基化允许合成碳水化合物衍生物甚至类似物。我们的研究结果显示，岩藻糖转移酶VI（EC 2.4.1.65）和III（EC 2.4.1.65），以及（2-3）-唾液酸转移酶ST3Gal III（EC 2.4.99.6）具有显著的合成潜力。我们演示了它们在制备寡糖及其衍生物和类似物方面的应用。
• Ernst, Beat; Dragic, Zorica; Marti, Sébastien, Chimia, 2001, vol. 55, # 4, p. 268 - 274
  作者：Ernst, Beat、Dragic, Zorica、Marti, Sébastien、Müller, Christian、Wagner, Beatrice、Jahnke, Wolfgang、Magnani, John L.、Norman, Keith E.、Oehrlein, Reinhold、Peters, Thomas、Kolb, Hartmuth C.

  DOI：——

  日期：——