carboxymethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside | 79360-19-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: carboxymethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
• 英文别名: 2-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylacetic acid
• CAS: 79360-19-3
• 化学式: C₁₆H₂₂O₁₁S
• 分子量: 422.41
• InChiKey: JRBJUJMGVZJRDN-NZBFACKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  177
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  L-lysyl-L-lysine dihydrochloride 、 carboxymethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 在 三乙胺 、 三氟乙酸 作用下， 生成 N²-2,N⁶-bis<<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)thio>acetyl>-L-lysyl>-N⁶-<<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)thio>acetyl>-L-lysine
  参考文献：
  名称：

  Cell-specific ligands for selective drug delivery to tissues and organs

  摘要：

  Various numbers of D-mannose residues have been attached via spacer arms to lysine, dilysine, and oligolysine backbones. These D-mannosyl peptide analogues were found to be potent competitive inhibitors of the uptake of 125I-labeled D-mannose-bovine serum albumin conjugate by rat alveolar macrophages. The inhibitory potency of these synthetic ligands increased with increasing number of carbohydrate moieties. The chirality of the peptide backbone did not appear to play a major role in binding, whereas variations of the length and linkage of the spacer arm notably affected the inhibitory activities. The saccharide specificity of the macrophage receptor was demonstrated by the inactivity of the corresponding D-galactosyl peptide analogues. The L-fucosyl peptide derivative was only weakly active. The trimannosyldilysine ligand (KI = 3.9 microM) and its analogues are potentially useful in selective delivery of therapeutic agents to macrophages.

  DOI：

  10.1021/jm00144a004
• 作为产物：
  描述：

  碘乙酸 、 1,2,3,4,6-O-五乙酰基-Alpha-甘露糖 在 三氟化硼乙醚 、 硫脲 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.75h， 以48%的产率得到carboxymethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  The synthesis and immune stimulating action of mannose-capped lysine-based dendrimers

  摘要：

  The syntheses of monodisperse lysine dendrimers, capped with two to sixty-four mono-, di- and tri-alpha-D-mannopyranosyl residues are described. These syntheses used reactive N-hydroxysuccinimide esters to ensure complete reaction of dendrimer amines with the mannosylating reagents. The purities of the dendrimers were established by RP-HPLC and MALDI-TOF mass spectrometry and were found to be excellent. The relative ability of these glycodendrimers to induce dendritic cell Maturation was measured, however, no significant trends were observed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.018

文献信息

• Cell-specific glycopeptide ligands
  申请人：Merck & Co., Inc.

  公开号：EP0063373B1

  公开（公告）日：1986-03-12