6-aminohexyl-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-(β-D-galactopyranosyl)-(1->4)-O-[(α-L-fucopyranosyl)-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside | 167475-62-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-aminohexyl-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-(β-D-galactopyranosyl)-(1->4)-O-[(α-L-fucopyranosyl)-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetamido-6-(6-aminohexoxy)-2-(hydroxymethyl)-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 167475-62-9
• 化学式: C₃₇H₆₅N₃O₂₃
• 分子量: 919.929
• InChiKey: OUXXAZZSHJXPKW-KNENCGRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.6
• 重原子数：
  63
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  418
• 氢给体数：
  15
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  6-aminohexyl-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-(β-D-galactopyranosyl)-(1->4)-O-[(α-L-fucopyranosyl)-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside 在 四丁基氢氧化铵 作用下， 以 水 为溶剂， 反应 96.0h， 以53%的产率得到6-aminohexyl O-(5-amino-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonic acid)-(2->3)-O-(β-D-glactopyranosyl)-(1->4)-O-[α-L-fucopyranosyl-(1->3)]-2-amino-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Kuznik; Unverzagt, Carlo; Hoersch, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 8, p. 745 - 752

  摘要：

  DOI：
• 作为产物：
  描述：

  6-(Z-氨基)-1-己醇 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 四丁基溴化铵 、 sodium methylate 、 sodium cyanoborohydride 、 1,1,3,3-四甲基脲 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.25h， 生成 6-aminohexyl-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-(β-D-galactopyranosyl)-(1->4)-O-[(α-L-fucopyranosyl)-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine

  摘要：

  The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00294-4

文献信息

• Oligosaccharide recognition by selectins: Synthesis and biological activity of multivalent sialyl lewis-X ligands
  作者：Gerhard Kretzschmar、Ulrich Sprengard、Horst Kunz、Eckart Bartnik、Wolfgang Schmidt、Alexander Toepfer、Brigitte Hörsch、Manfred Krause、Dirk Seiffge

  DOI：10.1016/0040-4020(95)00833-t

  日期：1995.11

  Trivalent sialyl Lewis-X ligands 6–8 anchored onto flexible templates have been synthesized and evaluated as inhibitors of E-selectin and P-selectin mediated cell adhesion in cell culture assays and in vivo. Biological activities in vitro correlated with spacer length and lead to ligands with 3-fold (E-selectin) and 5-fold (P-selectin) improved receptor binding avidity per single tetrasaccharide moiety

  已经合成了锚定在柔性模板上的三价唾液酸Lewis-X配体6-8，并在细胞培养测定和体内试验中将其作为E-选择蛋白和P-选择蛋白介导的细胞粘附的抑制剂进行了评估。体外生物活性与间隔物长度相关，并导致配体具有每个单四糖部分3倍（E-选择素）和5倍（P-选择素）改善的受体结合亲和力。
• Chemical and enzymatic synthesis of high-affinity selectin ligands
  作者：G. Kuznik、B. Hörsch、G. Kretzschmar、C. Unverzagt

  DOI：10.1016/s0960-894x(97)00051-6

  日期：1997.3

  Analogs of sialyl Lewis(x) have been synthesized chemically using donors of modified sialic acids. The sialic acids were obtained enzymatically by an aldolase reaction. The sLe(x) tetrasaccharides modified at C-2 of the GlcNAc moiety and at C-5 of the sialic acid residue were tested as inhibitors for E- and P-selectins. Up to 12-fold higher inhibitory potency was found for the lyse-derivative of sLeX compared to the parent compound. (C) 1997 Elsevier Science Ltd.
• Synthesis and biological activity of novel sialyl-lewisX conjugates
  作者：Ulrich Sprengard、Horst Kunz、Christoph Hüls、Wolfgang Schmidt、Dirk Seiffge、Gerhand Kretzshmar

  DOI：10.1016/0960-894x(96)00057-1

  日期：1996.3

  Novel sialyl Lewis(x) conjugates have been synthesized and evaluated as inhibitors of E- and P-selectin mediated cell adhesion in cell culture assays. The most potent conjugate in the static inhibition assays exhibited a significant and dose-dependent pharmacological potency as inhibitor of the endotoxin-induced leukocyte adhesion to the endothelium of postcapillary venules in rats.
• Kuznik; Unverzagt, Carlo; Hoersch, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 8, p. 745 - 752
  作者：Kuznik、Unverzagt, Carlo、Hoersch、Kretzschmar

  DOI：——

  日期：——
• Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine
  作者：Gerhard Kretzschmar、Wilhelm Stahl

  DOI：10.1016/s0040-4020(98)00294-4

  日期：1998.6

  The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.