phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-fucopyranoside | 211801-77-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-fucopyranoside
• 英文别名: phenyl 2,3,4-tri-O-benzyl-l-thio-β-L-fucopyranoside；(2R,3S,4S,5R,6S)-2-methyl-3,4,5-tris(phenylmethoxy)-6-phenylsulfanyloxane
• CAS: 211801-77-3
• 化学式: C₃₃H₃₄O₄S
• 分子量: 526.697
• InChiKey: WGAOZACWMVPQOY-GMHIYEQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-fucopyranoside 在 platinum(IV) oxide N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2,3,4-tri-O-benzyl-α-D-fucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-N-acetyl-2,3,6-tri-O-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：

  D-Fucose 在 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 12.0h， 生成 phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-fucopyranoside
  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

文献信息

• An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation
  作者：An-Hsiang Adam Chu、Andrei Minciunescu、Vittorio Montanari、Krishna Kumar、Clay S. Bennett

  DOI：10.1021/ol5004059

  日期：2014.3.21

  iodonium salt phenyl(trifluoroethyl)iodonium triflimide is shown to activate thioglycosides for glycosylation at room temperature. Both armed and disarmed thioglycosides rapidly undergo glycosylation in 68–97% yield. The reaction conditions are mild and do not require strict exclusion of air and moisture. The operational simplicity of the method should allow experimentalists with a limited synthetic background

  空气和水稳定的碘鎓盐苯基（三氟乙基）碘鎓三氟甲磺酰亚胺在室温下可激活硫代糖苷以进行糖基化。武装和解除武装的硫糖苷都以 68-97% 的产率迅速进行糖基化。反应条件温和，不需要严格排除空气和水分。该方法的操作简单性应该允许具有有限合成背景的实验者构建糖苷键。
• 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, Inhibitory Effects on Nitric Oxide and Structure-Activity Relationships of a Glycosphingolipid from the Marine Sponge Aplysinella rhax and Its Analogues
  作者：Yuzo Fujita、Naohiro Ohshima、Ai Hasegawa、Frank Schweizer、Tadahiro Takeda、Fumiyuki Kiuchi、Noriyasu Hada

  DOI：10.3390/molecules16010637

  日期：——

  The novel glycosphingolipid, b-D-GalNAcp(1®4)[a-D-Fucp(1®3)]-b-D-GlcNAcp(1®)Cer (A), isolated from the marine sponge Aplysinella rhax has a unique structure, with D-fucose and N-acetyl-D-galactosamine moieties attached to a reducing-end N-acetyl-D-glucosamine through an a1®3 and b1®4 linkage, respectively. We synthesized glycolipid 1 and some non-natural di- and trisaccharide analogues 2-6 containing a D-fucose residue. Among these compounds, the natural type showed the most potent nitric oxide (NO) production inhibitory activity against LPS-induced J774.1 cells. Our results indicate that both the presence of a D-Fuca1-3GlcNAc-linkage and the ceramide aglycon portion are crucial for optimal NO inhibition.

  从海洋海绵 Aplysinella rhax 中分离出的新型糖磷脂--b-D-GalNAcp(1®4)[a-D-Fucp(1®3)]-b-D-GlcNAcp(1®)Cer (A) 具有独特的结构，D-岩藻糖和 N-乙酰基-D-半乳糖胺分别通过 a1®3 和 b1®4 连接到还原端的 N-乙酰基-D-葡萄糖胺上。我们合成了糖脂 1 和一些含有 D-岩藻糖残基的非天然二糖和三糖类似物 2-6。在这些化合物中，天然型糖脂对 LPS 诱导的 J774.1 细胞一氧化氮（NO）产生的抑制活性最强。我们的研究结果表明，D-Fuca1-3GlcNAc 连接和神经酰胺苷元部分的存在对于达到最佳的一氧化氮抑制效果至关重要。
• Glycodiversification for the Optimization of the Kanamycin Class Aminoglycosides
  作者：Jinhua Wang、Jie Li、Hsiao-Nung Chen、Huiwen Chang、Christabel Tomla Tanifum、Hsiu-Hsiang Liu、Przemyslaw G. Czyryca、Cheng-Wei Tom Chang

  DOI：10.1021/jm050368c

  日期：2005.10.1

  In an effort to optimize the antibacterial activity of kanamycin class aminoglycoside antibiotics, we have accomplished the synthesis and antibacterial assay of new kanamycin B analogues. A rationale-based glycodiversification strategy was employed. The activity of the lead is comparable to that of commercially available kanamycin. These new members, however, were found to be inactive against aminoglycoside resistant bacteria. Molecular modeling was used to provide the explanation. Thus, a new strategy for structural modifications of kanamycin class aminoglycosides is suggested.
• Synthesis and biological activities of glycosphingolipid analogues from marine sponge Aplysinella rhax
  作者：Noriyasu Hada、Taishi Nakashima、Suraj Prakash Shrestha、Ryo Masui、Yuji Narukawa、Kayoko Tani、Tadahiro Takeda

  DOI：10.1016/j.bmcl.2007.07.108

  日期：2007.11

  A novel glycosphingolipid, P-D-GalNAcp(l -> 4)[alpha-D- Fucp(1 -> 3)]-beta-D-GIcNAcp(1 -> 3)Cer(1), isolated from the marine sponge Aplysinella rhax, has a unique structure, with D-fucose and N-acetyl-D-galactosamine attached to a reducing-end N-acetyl-D-glucosamine through an alpha 1 -> 3 and beta 1 -> 4 linkage, respectively. We synthesized glycolipid analogues carrying a 2-branched fatty alkyl residue or a 2-trimethylsilyl ethyl residue in place of ceramide (2 and 3), non-natural type trisaccharide analogue containing an L-fucose residue (4), and other analogues (5 and 6). Among these prepared compounds, 2 showed the most potent nitric oxide (NO) production inhibitory activity against LPS-activated J774.1 cells. In addition, their structure-activity relationships were established. (c) 2007 Elsevier Ltd. All rights reserved.