p-tolyl 2,3-di-O-benzyl-5-O-toluenesulfonyl-1-thio-β-D-xylofuranoside | 887747-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2,3-di-O-benzyl-5-O-toluenesulfonyl-1-thio-β-D-xylofuranoside
• 英文别名: [(2R,3S,4R,5S)-5-(4-methylphenyl)sulfanyl-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 887747-56-0
• 化学式: C₃₃H₃₄O₆S₂
• 分子量: 590.761
• InChiKey: FGKSLLONVDMHGE-LVVLYVGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-tolyl 2,3-di-O-benzyl-5-O-toluenesulfonyl-1-thio-β-D-xylofuranoside 在 silver trifluoromethanesulfonate N-碘代丁二酰亚胺 、 18-冠醚-6 、 4 A molecular sieve 、 氨 、 sodium 、 phosphorus pentoxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 13.25h， 生成 methyl 5-deoxy-5-methylthio-α-D-xylofuranoside
  参考文献：
  名称：

  The 5-Deoxy-5-methylthio-xylofuranose Residue in Mycobacterial Lipoarabinomannan. Absolute Stereochemistry, Linkage Position, Conformation, and Immunomodulatory Activity

  摘要：

  Mycobacteria produce a cell-surface glycoconjugate, lipoarabinomannan (LAM), which has been shown to be a potent modulator of the immune response that arises from infection by these organisms. Recently, LAM from the human pathogens Mycobacterium tuberculosis and M. kansasii has been shown to contain an unusual 5-deoxy-5-methylthio-xylofuranose (MTX) residue as well as its corresponding oxidized counterpart, 5-deoxy-5-methylsulfoxy-xylofuranose (MSX). To date, the absolute configuration of these residues and their linkage position to the polysaccharide are unknown, as is their biological role. Through the combined use of chemical synthesis and NMR spectroscopy, we have established that the MTX/MSX residues in these glycoconjugates are of the D-configuration and that they are linked alpha-(1-4) to a mannopyranose residue in the mannan portion of the glycan. Conformational analysis of the MTX/MSX residue using NMR spectroscopy showed differences in ring conformation and as well as in the rotamer populations about the C-4-C-5 bond, as compared to the parent compound, methyl alpha-D-xylofuranoside. Two of the synthesized disaccharides, 3 and 34, were tested in cytokine induction assays, and neither led to the production of TNF-alpha or IL-12p70. In contrast, both demonstrated modest inhibitory properties when these same cytokines were induced using a preparation of Interferon-gamma and Staphylococcus aureus Cowan strain (SAC/IFN-gamma). These latter observations suggest that this motif may play a role in the immune response arising from mycobacterial infection.

  DOI：

  10.1021/ja057373q
• 作为产物：
  描述：

  p-tolyl 2,3-di-O-benzyl-5-O-trityl-1-thio-β-D-xylofuranoside 在 吡啶 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 p-tolyl 2,3-di-O-benzyl-5-O-toluenesulfonyl-1-thio-β-D-xylofuranoside
  参考文献：
  名称：

  The 5-Deoxy-5-methylthio-xylofuranose Residue in Mycobacterial Lipoarabinomannan. Absolute Stereochemistry, Linkage Position, Conformation, and Immunomodulatory Activity

  摘要：

  Mycobacteria produce a cell-surface glycoconjugate, lipoarabinomannan (LAM), which has been shown to be a potent modulator of the immune response that arises from infection by these organisms. Recently, LAM from the human pathogens Mycobacterium tuberculosis and M. kansasii has been shown to contain an unusual 5-deoxy-5-methylthio-xylofuranose (MTX) residue as well as its corresponding oxidized counterpart, 5-deoxy-5-methylsulfoxy-xylofuranose (MSX). To date, the absolute configuration of these residues and their linkage position to the polysaccharide are unknown, as is their biological role. Through the combined use of chemical synthesis and NMR spectroscopy, we have established that the MTX/MSX residues in these glycoconjugates are of the D-configuration and that they are linked alpha-(1-4) to a mannopyranose residue in the mannan portion of the glycan. Conformational analysis of the MTX/MSX residue using NMR spectroscopy showed differences in ring conformation and as well as in the rotamer populations about the C-4-C-5 bond, as compared to the parent compound, methyl alpha-D-xylofuranoside. Two of the synthesized disaccharides, 3 and 34, were tested in cytokine induction assays, and neither led to the production of TNF-alpha or IL-12p70. In contrast, both demonstrated modest inhibitory properties when these same cytokines were induced using a preparation of Interferon-gamma and Staphylococcus aureus Cowan strain (SAC/IFN-gamma). These latter observations suggest that this motif may play a role in the immune response arising from mycobacterial infection.

  DOI：

  10.1021/ja057373q

文献信息

• IMMUNOMODULATORY SACCHARIDE COMPOUNDS
  申请人：Lowary L. Todd

  公开号：US20070219144A1

  公开（公告）日：2007-09-20

  Compounds comprising a saccharide molecule and a 5-deoxy-5-methylthio-xylofuranose (MTX) moiety or a 5-deoxy-5-methylsulfoxy-xylofuranose (MSX) moiety, and use of such compounds in methods for modulating inflammation and immune responses.

  包含糖分子和5-去氧-5-甲硫氧基-木糖呋喃糖（MTX）基团或5-去氧-5-甲基磺氧基-木糖呋喃糖（MSX）基团的化合物，以及在调节炎症和免疫反应方法中使用这些化合物。
• Synthesis and biotinylation of oligosaccharide fragments of mannosylated and 5-deoxy-5-methylthio-xylofuranosylated lipoarabinomannan from Mycobacterium tuberculosis
  作者：Pintu Kumar Mandal、Pratik Rajesh Chheda

  DOI：10.1016/j.carres.2015.01.003

  日期：2015.4

  The attachment of biotin to a molecule provides a powerful tool in biology. Here, we report an efficient synthesis and biotinylation of mannosylated and 5-deoxy-5-methylthio-xylofuranosylated Lipoarabinomannan from Mycobacterium tuberculosis. Preparation of the oligosaccharides involved the sequential addition of thioglycoside donors with arabinofuranosyl-containing acceptors. Methylthio group was introduced near the end of the synthesis. (C) 2015 Elsevier Ltd. All rights reserved.
• The 5-Deoxy-5-methylthio-xylofuranose Residue in Mycobacterial Lipoarabinomannan. Absolute Stereochemistry, Linkage Position, Conformation, and Immunomodulatory Activity
  作者：Maju Joe、Daniel Sun、Hashem Taha、Gladys C. Completo、Joanne E. Croudace、David A. Lammas、Gurdyal S. Besra、Todd L. Lowary

  DOI：10.1021/ja057373q

  日期：2006.4.1

  Mycobacteria produce a cell-surface glycoconjugate, lipoarabinomannan (LAM), which has been shown to be a potent modulator of the immune response that arises from infection by these organisms. Recently, LAM from the human pathogens Mycobacterium tuberculosis and M. kansasii has been shown to contain an unusual 5-deoxy-5-methylthio-xylofuranose (MTX) residue as well as its corresponding oxidized counterpart, 5-deoxy-5-methylsulfoxy-xylofuranose (MSX). To date, the absolute configuration of these residues and their linkage position to the polysaccharide are unknown, as is their biological role. Through the combined use of chemical synthesis and NMR spectroscopy, we have established that the MTX/MSX residues in these glycoconjugates are of the D-configuration and that they are linked alpha-(1-4) to a mannopyranose residue in the mannan portion of the glycan. Conformational analysis of the MTX/MSX residue using NMR spectroscopy showed differences in ring conformation and as well as in the rotamer populations about the C-4-C-5 bond, as compared to the parent compound, methyl alpha-D-xylofuranoside. Two of the synthesized disaccharides, 3 and 34, were tested in cytokine induction assays, and neither led to the production of TNF-alpha or IL-12p70. In contrast, both demonstrated modest inhibitory properties when these same cytokines were induced using a preparation of Interferon-gamma and Staphylococcus aureus Cowan strain (SAC/IFN-gamma). These latter observations suggest that this motif may play a role in the immune response arising from mycobacterial infection.