(2R,4S,5R,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-6-[3-[3-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[(2R,4S,5R,6R)-2-carboxy-4-hydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxypropyldisulfanyl]propoxy]-3,4-dihydroxyoxan-2-yl]methoxy]-4-hydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid | 1251774-11-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5R,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-6-[3-[3-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[(2R,4S,5R,6R)-2-carboxy-4-hydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxypropyldisulfanyl]propoxy]-3,4-dihydroxyoxan-2-yl]methoxy]-4-hydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 1251774-11-4
• 化学式: C₄₄H₇₄N₄O₃₀S₂
• 分子量: 1203.21
• InChiKey: XPKOKXDCFDPJCJ-WZSNLKMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.3
• 重原子数：
  80
• 可旋转键数：
  31
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  599
• 氢给体数：
  20
• 氢受体数：
  32

反应信息

• 作为产物：
  描述：

  在 吡啶 、 甲醇 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 水 、 sodium methylate 、 caesium carbonate 、 三乙胺 、 lithium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 75.0h， 生成 (2R,4S,5R,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-6-[3-[3-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[(2R,4S,5R,6R)-2-carboxy-4-hydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxypropyldisulfanyl]propoxy]-3,4-dihydroxyoxan-2-yl]methoxy]-4-hydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of N-modified sTn analogs and evaluation of their immunogenicities by microarray-based immunoassay

  摘要：

  A series of sin derivative-keyhole limpet hemocyanin (KLH) conjugates were synthesized, and their immunogenicities were evaluated by corresponding IgG production. To achieve a high-throughput screening immunoassay, a glycan microarray with sTn and its analogs was used to detect the production of corresponding antibodies in mouse sera. The immunoassay results revealed that the derived sTn antigens are generally more immunogenic than the parent sTn antigen. The N-propionyl sTn antigen was the most immunogenic among the sTn derivatives investigated, and its antiserum was cross-reactive with natural sin. These results indicate that N-propionyl sTn may serve as a viable vaccine candidate to produce antibody for detection of sTn antigen. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.050

文献信息

• Synthesis of N-modified sTn analogs and evaluation of their immunogenicities by microarray-based immunoassay
  作者：Sk Sahabuddin、Tsung-Che Chang、Chang-Ching Lin、Fan-Dan Jan、Hsuan-Yi Hsiao、Kuo-Ting Huang、Jeen-Han Chen、Jia-Cherng Horng、Ja-an Annie Ho、Chun-Cheng Lin

  DOI：10.1016/j.tet.2010.07.050

  日期：2010.9

  A series of sin derivative-keyhole limpet hemocyanin (KLH) conjugates were synthesized, and their immunogenicities were evaluated by corresponding IgG production. To achieve a high-throughput screening immunoassay, a glycan microarray with sTn and its analogs was used to detect the production of corresponding antibodies in mouse sera. The immunoassay results revealed that the derived sTn antigens are generally more immunogenic than the parent sTn antigen. The N-propionyl sTn antigen was the most immunogenic among the sTn derivatives investigated, and its antiserum was cross-reactive with natural sin. These results indicate that N-propionyl sTn may serve as a viable vaccine candidate to produce antibody for detection of sTn antigen. (C) 2010 Elsevier Ltd. All rights reserved.