phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside | 478687-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside
• 英文别名: phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-galactopyranoside；phenyl 2,4,6-tri-O-benzyl-3-deoxy-thio-β-D-galactopyranoside
• CAS: 478687-09-1
• 化学式: C₃₃H₃₄O₄S
• 分子量: 526.697
• InChiKey: HEOMKRJZGAKTGF-VDYOSWSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside 在 platinum(IV) oxide 、 palladium dihydroxide N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 氢气 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-N-acetyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  The synthesis of deoxy-α-Gal epitope derivatives for the evaluation of an anti-α-Gal antibody binding

  摘要：

  alpha-Gal epitopes (also termed as alpha-Gal) are carbohydrate structures bearing the alpha-D-Gal-(1 --> 3)-beta-D-Gal terminus 1 and are known to be the antigen responsible for antibody-mediated hyperacute rejection in xenotransplantation. Terminal 2-, 3-, 4-, and 6-deoxy-Gal derivatives of alpha-Gal were synthesized. Inhibition ELISA using mouse laminin was established to determine the binding affinity of the synthesized alpha-Gal derivatives. 4-Deoxy-alpha-Gal derivative 7 showed a significant reduction in antibody recognition. The IC50 value was 15-fold poorer than the standard alpha-Gal epitopes alpha-D-Gal-(1 --> 3)-beta-D-Gal-(1 --> 4)-beta-D-Glc-NHAc (39) and alpha-D-Gal-(1 --> 3)-beta-D-Gal-(1 -- 4)-beta-D-Glc-OBn (40). A similar observation was seen with 2-deoxy-alpha-Gal derivative 5, whose IC50 value was nearly tenfold higher than the standards. Interestingly, substitution at the terminal 3-position resulted in only a fourfold decrease in antibody recognition, suggesting a possible point of future derivation. Finally, 6-deoxy-alpha-Gal derivative 8 exhibited similar antibody recognition to both alpha-Gal epitope 39 and alpha-Gal epitope 40. This strongly suggests that derivatization at the 6-position can be accomplished without loss of antibody recognition. These findings can be utilized for the future design of other alpha-Gal derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00159-3
• 作为产物：
  描述：

  phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 在 三乙基硅烷 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside
  参考文献：
  名称：

  全合成荧光假单胞菌O特异多糖的三糖重复单元BIM B-582

  摘要：

  报道了荧光假单胞菌BIM B-582的O-特异性多糖的三糖重复单元的第一全合成。这种高效的合成涉及连续1,2-顺式的糖基化包括β-升-rhamnosylation和α选择性稀有4-脱氧的耦合d -木糖-hexose作为关键步骤。合成的三糖在还原端配有一个氨基丙基接头，以便与蛋白质和微阵列结合，以进行进一步的免疫学研究。

  DOI：

  10.1021/acs.orglett.8b02669

文献信息

• Synthesis and Structure−Activity Relationship Study of Isoglobotrihexosylceramide Analogues
  作者：Wenlan Chen、Chengfeng Xia、Jinhua Wang、Prakash Thapa、Yusen Li、Janos Nadas、Wenpeng Zhang、Dapeng Zhou、Peng George Wang

  DOI：10.1021/jo701539k

  日期：2007.12.1

  killer T (iNKT) cells are innate T lymphocytes that express T cell receptors binding to exogenous and endogenous glycosphingolpid antigens presented by a nonpolymorphic, non-MHC antigen presenting molecule, CD1d. The endogenous glycosphingolipid metabolite, isoglobotrihexosylceramide (iGb3), is the first known natural ligand for both human and mouse iNKT cells, whose activity has been confirmed in a

  不变的自然杀伤性T细胞（iNKT）是先天性T淋巴细胞，表达表达与非多态性，非MHC抗原呈递分子CD1d呈递的外源性和内源性糖鞘脂抗原结合的T细胞受体。内源性鞘糖脂代谢物即异三糖三己糖基神经酰胺（iGb3）是人类和小鼠iNKT细胞的第一个已知天然配体，其活性已在由不同研究人员产生的多种iNKT细胞克隆中得到证实，代表了大部分iNKT细胞群体。T细胞受体介导的信号通路在很大程度上受到糖鞘脂抗原结构变异的影响，从而导致iNKT细胞具有多种多样的生物学功能。为了研究iGb3触发iNKT细胞激活背后的结构要求，iGb3的结构活性关系（SAR）需要进行表征。在这项研究中，合成了包含2'''，3'''，4'''和6'''脱氧末端半乳糖的iGb3类似物，以探测iGb3和TCR之间的SAR。使用鼠iNKT细胞杂交瘤DN32.D3对合成iGb3类似物进行了生物学检测。结果表明，末端半乳糖的2'''和3'''羟
• Synthesis and evaluation of 3″- and 4″-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000
  作者：Ravinder Raju、Bernard F. Castillo、Stewart K. Richardson、Meena Thakur、Ryan Severins、Mitchell Kronenberg、Amy R. Howell

  DOI：10.1016/j.bmcl.2009.06.005

  日期：2009.8

  Four 3 ''- and 4 ''-deoxy and -fluorogalactosyl ceramides were synthesized, and their ability to stimulate iNKT cells, based on levels of IL-2 production, was assessed in three NKT cell receptor hybridomas. In two of the hybridomas, 1.2 and 2H4, all of the analogs were immunostimulatory, while in the 1.4 hybridoma only the 4 ''-fluoro analog led to the production of significant levels of IL-2. (C) 2009 Elsevier Ltd. All rights reserved.