1-chloro-3,6-dioxa-8-octyl 3-O-p-methoxybenzyl-β-D-galactoside | 274258-26-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-chloro-3,6-dioxa-8-octyl 3-O-p-methoxybenzyl-β-D-galactoside
• 英文别名: 2-[2-(2-Chloroethoxy)ethoxy]ethyl 3-O-p-methoxybenzyl-β-D-galactopyranoside；(2R,3R,4S,5S,6R)-2-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]-6-(hydroxymethyl)-4-[(4-methoxyphenyl)methoxy]oxane-3,5-diol
• CAS: 274258-26-3
• 化学式: C₂₀H₃₁ClO₉
• 分子量: 450.914
• InChiKey: DFTUGJWQZIVPBR-UJMXGEILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-chloro-3,6-dioxa-8-octyl 3-O-p-methoxybenzyl-β-D-galactoside 在 platinum(IV) oxide 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 2,6-二叔丁基-4-甲基吡啶 、 ammonium cerium(IV) nitrate 、 4 A molecular sieve 、 氢气 、 三氟甲烷磺酸甲酯 作用下， 以 甲醇 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 80.0 ℃ 、405.3 kPa 条件下， 反应 56.0h， 生成 Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-6-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
  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：

  1-Chloro-3,6-dioxaoct-8-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 二正丁基氧化锡 、 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 44.0h， 生成 1-chloro-3,6-dioxa-8-octyl 3-O-p-methoxybenzyl-β-D-galactoside
  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

文献信息

• Methods and formulations for reducing circulating antibodies
  申请人：——

  公开号：US20010010818A1

  公开（公告）日：2001-08-02

  The invention provides methods for reducing circulating levels of antibodies, particularly disease-associated antibodies. The methods entail administering effective amounts of epitope-presenting carriers to an individual. In other embodiments, ex vivo methods for reducing circulating levels of antibodies are provided which employ epitope-presenting carriers.

  本发明提供了降低循环抗体水平的方法，特别是疾病相关抗体。该方法包括向个体施用有效剂量的表位呈现载体。在其他实施例中，本发明提供了利用表位呈现载体的体外降低循环抗体水平的方法。
• Conjugates comprising galactose alpha 1,3 galactosyl epitopes and methods of using same
  申请人：——

  公开号：US20020160964A1

  公开（公告）日：2002-10-31

  This invention provides conjugates useful for xenotransplantation which comprise a galactose &agr;1,3 galactosyl (&agr;Gal) epitope conjugated to a valency platform molecule, preferably a chemically defined valency platform molecule which allows precise valency. The invention also provides compositions comprising these conjugates, and methods (such as methods for inducing tolerance) using these conjugates and compositions.

  该发明提供了用于异种移植的共轭物，其包括将半乳糖α1,3半乳糖基（αGal表位）与价数平台分子结合而成，优选为化学定义的价数平台分子，以允许精确的价数。该发明还提供了包括这些共轭物的组合物，以及使用这些共轭物和组合物的方法（例如诱导耐受的方法）。
• METHODS AND FORMULATIONS FOR REDUCING CIRCULATING ANTIBODIES
  申请人：LA JOLLA PHARMACEUTICAL

  公开号：EP1135167A2

  公开（公告）日：2001-09-26
• CONJUGATES COMPRISING GALACTOSE ALPHA 1,3 GALACTOSYL EPITOPES AND METHODS OF USING SAME
  申请人：LA JOLLA PHARMACEUTICAL

  公开号：EP1137652A2

  公开（公告）日：2001-10-04
• US6399578B1
  申请人：——

  公开号：US6399578B1

  公开（公告）日：2002-06-04