1,2,3,6-tetra-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-α-D-galactopyranosyl]galactopyranoside | 585530-92-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3,6-tetra-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-α-D-galactopyranosyl]galactopyranoside
• 英文别名: acetyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α/β-D-galactopyranoside；[(2R,3S,4S,5R,6R)-4,5-Diacetyloxy-6-[(2R,3S,4S,5R)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxy-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 585530-92-3
• 化学式: C₄₀H₅₄O₂₇
• 分子量: 966.853
• InChiKey: NNLVGZFZQQXQNW-ASONLROBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  67
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  335
• 氢给体数：
  0
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  1,2,3,6-tetra-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-α-D-galactopyranosyl]galactopyranoside 生成 [(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-[(2R,3S,4S,5R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-bromooxan-3-yl]oxy-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  NAIR, V. G.;JOSEPH, J. P.;BERNSTEIN, S.

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4S,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 、 乙酸酐 生成 1,2,3,6-tetra-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-α-D-galactopyranosyl]galactopyranoside
  参考文献：
  名称：

  NAIR, V. G.;JOSEPH, J. P.;BERNSTEIN, S.

  摘要：

  DOI：

文献信息

• Influence of saccharide size on the cellular immune response to glycopeptides
  作者：Mickael Mogemark、Thomas P. Cirrito、Petter Sjölin、Emil R. Unanue、Jan Kihlberg

  DOI：10.1039/b301747h

  日期：——

  trigalactosylated derivative of an immunogenic peptide from hen egg-white lysozyme (HEL52-61) was prepared. Synthesis was accomplished by assembly of an alpha-1,4-linked trigalactose peracetate which was coupled to Fmoc serine. After activation as a pentafluorophenyl ester the resulting building block was used in solid-phase synthesis In contrast to the corresponding mono- and digalactosylated derivatives of HEL52-61

  与抗原呈递细胞上的MHC分子结合的糖肽可能会诱发碳水化合物选择性T细胞。为了研究细胞免疫应答如何取决于碳水化合物部分的大小，制备了一种来自鸡蛋清溶菌酶（HEL52-61）的免疫原性肽的三半乳糖基化衍生物。通过组装与Fmoc丝氨酸偶联的α-1，4-连接的三半乳糖过乙酸酯来完成合成。活化为五氟苯基酯后，将所得结构单元用于固相合成。与HEL52-61的相应单-和半乳糖基化衍生物相反，三乳糖基化的HEL52-61没有免疫原性。有点令人惊讶 发现这是因为三半乳糖基衍生物与I-Ak MHC分子的结合比单半乳糖基和二半乳糖基肽弱约两个数量级。我们的观察结果为以前的发现提供了解释，这些发现表明从自然界中的MHC分子中分离出的糖肽通常携带小糖。
• Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and ‘click’ conjugation
  作者：Hilbert M. Branderhorst、Raymond Kooij、Annika Salminen、Lieneke H. Jongeneel、Christopher J. Arnusch、Rob M. J. Liskamp、Jukka Finne、Roland J. Pieters

  DOI：10.1039/b800283e

  日期：——

  A galabiose disaccharide building block was synthesized by an efficient pectinase cleavage of polygalacturonic acid and subsequent chemical functional group transformations. Besides the disaccharide, the corresponding trisaccharide was also obtained and modified. The compounds were subsequently conjugated to dendrimers with up to eight end groups using 'click' chemistry. The compounds were evaluated

  通过聚半乳糖醛酸的有效果胶酶切割和随后的化学官能团转化合成了半乳糖二糖结构单元。除了二糖以外，还获得并改性了相应的三糖。随后使用“点击”化学将化合物缀合至具有最多八个端基的树枝状聚合物。在血凝测定中，将这些化合物评估为病原体猪链球菌粘附的抑制剂，并且对四价和八价半乳糖酶化合物的MIC值均在低纳摩尔范围内观察到了强抑制作用。相应的八价三糖为约。抑制剂弱20倍。