8-methoxycarbonyloct-1-yl O-α-D-galactopyranosyl-(1-3)-O-β-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxy-β-D-glucopyranoside | 97205-12-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-methoxycarbonyloct-1-yl O-α-D-galactopyranosyl-(1-3)-O-β-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: methyl 9-[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxynonanoate
• CAS: 97205-12-4
• 化学式: C₃₀H₅₃NO₁₈
• 分子量: 715.747
• InChiKey: VUVXOXPLAVPCED-SZSBHTTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  49
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  293
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  UDP-Gal 、 8-methoxycarbonyloct-1-yl O-α-D-galactopyranosyl-(1-3)-O-β-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxy-β-D-glucopyranoside 在 苯磺酰胺 、 phosphate buffered saline solution bovine α-1,3-galactosyltransferase 、 manganese(ll) chloride 、 alkaline phosphatase 作用下， 反应 168.0h， 以9.6%的产率得到8-methoxycarbonyloctyl α-D-galactopyranosyl-(1->3)-α-D-galactopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-β-D-2-deoxy-2-acetamidoglucopyranoside
  参考文献：
  名称：

  Frontal Affinity Chromatography Coupled to Mass Spectrometry: An Effective Method for K_dDetermination and Screening of α‐Gal Derivatives Binding to Anti‐Gal Antibodies (IgG)

  摘要：

  Frontal affinity chromatography with mass spectrometric detection (FAC/MS) was developed as an effective method for rapid determination of K-d values for alpha-Gal derivatives binding to human anti-Gal IgG antibodies. Using this method, K-d values for 23 alpha-Gal compounds were determined for the first time, including an alpha-Gal terminated N-linked oligosaccharide which mimics a single N-glycoform present on the surface of animal cells. A mixture of eight alpha-Gal derivatives, a model for an alpha-Gal compound library, was successfully screened against this anti-Gal IgG using FAC/MS. The analyte breakthrough sequence, indicated by the ion chromatogram, reflected the magnitude of the K-d values, confirming its potential application in the screening of new alpha-Gal derivatives and mimetics. Ten alpha-Gal derivatives were designed and synthesized chemically or enzymatically. Among the compounds analyzed, trivalent compound 26 demonstrated the strongest binding affinity to anti-Gal IgG with a K-d value of 3.1 muM. The alpha-Gal terminated N-linked oligosaccharide 28 had a K-d value of 8.6 muM.

  DOI：

  10.1081/car-120025323
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 以75%的产率得到8-methoxycarbonyloct-1-yl O-α-D-galactopyranosyl-(1-3)-O-β-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  8-甲氧基羰基辛-1-基O-α-d-吡喃半乳糖基-（1→3）-O-β-d-吡喃半乳糖基-（1→4）-2-乙酰氨基-2-脱氧-β-d-的合成吡喃葡萄糖苷

  摘要：

  摘要卤化物辅助的糖基化反应是通过在糖基卤中使用非参与的2位取代基（苄基）来获得的α-d-半乳糖基键和三氟甲磺酸银与参与的2位取代基（苯甲酰基）的促进作用而获得的标题三糖衍生物的简便合成中的β-d-半乳糖基键。该合成方法还包括使用稳定的硫代糖苷中间体，这些中间体容易转化为合适的半乳糖基溴化物，以及分别通过环选择性，还原性和酸催化的环状缩醛和原酸酯开口，以获得所需的中间体。

  DOI：

  10.1016/0008-6215(85)85197-1

文献信息

• Acceptor hydroxyl group mapping for calf thymus α-(1 → 3) - galactosyltransferase and enzymatic synthesis of α-d-Galp-(1 → 3)-β-d-Gal p-(1 → 4)-βd-GlcpNAc analogs
  作者：Keiko Sujino、Carles Malet、Ole Hindsgaul、Monica M. Palcic

  DOI：10.1016/s0008-6215(97)00268-1

  日期：1997.12

  Abstract The epitope of the acceptor substrate for α -(1 → 3)-galactosyltransferase from calf thymus has been mapped by using a series of mono-deoxygenated and mono- O -alkylated Type II (β- d - Gal p-(1 → 4)-β- d - Glc p NAc ) disaccharides. The 4-OH group of the β- d -galactopyranosyl residue is a key polar group essential for glycosyl transfer, tolerating neither deoxygenation nor O -alkylation

  摘要：利用一系列单脱氧和单-O-烷基化的II型（β-d-Galp-（1→ 4）-β-d-Glcp NAc）二糖。β-d-吡喃半乳糖基残基的4-OH基是糖基转移所必需的关键极性基团，既不耐受脱氧也不耐受O-烷基化。易于容许在6和6'位被各种极性烷基取代基取代，从而允许制备酶促合成一系列在每个羟基上带有极性取代基的三糖衍生物。这些新的类似物是艰难梭菌毒素A和人抗α-Gal抗体的潜在抑制剂。
• On the preparative use of recombinant pig α(1–3)galactosyl-transferase
  作者：Gabi Baisch、Reinhold Öhrlein、Frank Kolbinger、Markus Streiff

  DOI：10.1016/s0960-894x(98)00266-2

  日期：1998.6

  A series of non-natural N-acyl derivatives of lactosamine is incubated with recombinant alpha(1-3)galactosyl-transferase and UDP-galactose. The enzyme shows a high promiscuity towards the nonnatural accepters. It selectively transfers a galactose unit onto the 3-OH group of the terminal beta-linked galactose in an alpha-mode to give an array of linear-B trisaccharides. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A synthesis of 8-methoxycarbonyloct-1-yl O-α-d-galactopyranosyl-(1→3)-O-β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside
  作者：Per J. Garegg、Stefan Oscarson

  DOI：10.1016/0008-6215(85)85197-1

  日期：1985.2

  obtain the α- d -galactosyl linkage and silver triflate promotion with a participating 2-substituent (benzoyl) was used to obtain the β- d -galactosyl linkage in a facile synthesis of the title trisaccharide derivative. The synthesis also incorporates the use of stable thioglycoside intermediates, easily converted into the appropriate galactosyl bromides, as well as regioselective, reductive and acid-catalysed

  摘要卤化物辅助的糖基化反应是通过在糖基卤中使用非参与的2位取代基（苄基）来获得的α-d-半乳糖基键和三氟甲磺酸银与参与的2位取代基（苯甲酰基）的促进作用而获得的标题三糖衍生物的简便合成中的β-d-半乳糖基键。该合成方法还包括使用稳定的硫代糖苷中间体，这些中间体容易转化为合适的半乳糖基溴化物，以及分别通过环选择性，还原性和酸催化的环状缩醛和原酸酯开口，以获得所需的中间体。
• Frontal Affinity Chromatography Coupled to Mass Spectrometry: An Effective Method for K_dDetermination and Screening of α‐Gal Derivatives Binding to Anti‐Gal Antibodies (IgG)
  作者：Jianqiang Wang、Boyan Zhang、Jianwen Fang、Keiko Sujino、Hong Li、Albin Otter、Ole Hindsgaul、Monica M. Palcic、Peng George Wang

  DOI：10.1081/car-120025323

  日期：2003.1.10

  Frontal affinity chromatography with mass spectrometric detection (FAC/MS) was developed as an effective method for rapid determination of K-d values for alpha-Gal derivatives binding to human anti-Gal IgG antibodies. Using this method, K-d values for 23 alpha-Gal compounds were determined for the first time, including an alpha-Gal terminated N-linked oligosaccharide which mimics a single N-glycoform present on the surface of animal cells. A mixture of eight alpha-Gal derivatives, a model for an alpha-Gal compound library, was successfully screened against this anti-Gal IgG using FAC/MS. The analyte breakthrough sequence, indicated by the ion chromatogram, reflected the magnitude of the K-d values, confirming its potential application in the screening of new alpha-Gal derivatives and mimetics. Ten alpha-Gal derivatives were designed and synthesized chemically or enzymatically. Among the compounds analyzed, trivalent compound 26 demonstrated the strongest binding affinity to anti-Gal IgG with a K-d value of 3.1 muM. The alpha-Gal terminated N-linked oligosaccharide 28 had a K-d value of 8.6 muM.