8-methoxycarbonyloctyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside | 64448-43-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-methoxycarbonyloctyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: 8-methoxycarbonyloctyl-β-D-lactoside；8-methoxycarbonyloctyl β-lactoside；methyl 9-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxynonanoate
• CAS: 64448-43-7；71721-48-7；71721-49-8；71721-50-1；71721-51-2；70761-83-0
• 化学式: C₂₂H₄₀O₁₃
• 分子量: 512.552
• InChiKey: AVTFACKDPIRTQK-KSFLKEQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  205
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  8-methoxycarbonyloctyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 以90%的产率得到8-carboxyoctyl O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of multivalent β-lactosyl clusters as potential tumor metastasis inhibitors

  摘要：

  A beta-lactosyl residue was linked to the amino groUpS Of L-lysyl-L-lysine through spacer arms of three different lengths (C2, C4, and C-9) to give trivalent beta-lactosyl clusters in order to increase the inhibitory activity of the beta-lactosyl group against tumor cell colonization. Thus, O-(2,3,4,6-tetra-0-acetyl-beta-D-galactopyranosyl)-(1 --> 4)-2,3,6-tri-O-acetyl-glucopyranosyl trichloroacetimidate was treated with methyl or benzyl hydroxyethanoate, methyl or benzyl 4-hydroxybutanoate, and methyl 9-hydroxynonanoate, respectively, in the presence of trimethylsilyl trifluoromethanesulfonate to give the corresponding beta-lactosides. These were coupled to L-lysyl-L-lysine, after conversion to the N-hydroxysuccinimide esters, to yield the corresponding trivalent beta-lactosyl-L-lysyl-L-lysine conjugates in good yields. The beta-lactosyl group with a C4 spacer arm was also coupled similarly to poly(L-lysine) (M(r) 3800) to form a polyvalent beta-lactosyl cluster. Coinjection of the trivalent (with C2 and C4 spacer arms) and polyvalent beta-lactosyl clusters with the highly metastatic B16 murine melanoma cells inhibited the formation of lung colonies in C57/BL mice, whereas the trivalent cluster with a C-9 spacer arm displayed no activity.

  DOI：

  10.1016/0008-6215(93)80071-l
• 作为产物：
  描述：

  2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 生成 8-methoxycarbonyloctyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of multivalent β-lactosyl clusters as potential tumor metastasis inhibitors

  摘要：

  A beta-lactosyl residue was linked to the amino groUpS Of L-lysyl-L-lysine through spacer arms of three different lengths (C2, C4, and C-9) to give trivalent beta-lactosyl clusters in order to increase the inhibitory activity of the beta-lactosyl group against tumor cell colonization. Thus, O-(2,3,4,6-tetra-0-acetyl-beta-D-galactopyranosyl)-(1 --> 4)-2,3,6-tri-O-acetyl-glucopyranosyl trichloroacetimidate was treated with methyl or benzyl hydroxyethanoate, methyl or benzyl 4-hydroxybutanoate, and methyl 9-hydroxynonanoate, respectively, in the presence of trimethylsilyl trifluoromethanesulfonate to give the corresponding beta-lactosides. These were coupled to L-lysyl-L-lysine, after conversion to the N-hydroxysuccinimide esters, to yield the corresponding trivalent beta-lactosyl-L-lysyl-L-lysine conjugates in good yields. The beta-lactosyl group with a C4 spacer arm was also coupled similarly to poly(L-lysine) (M(r) 3800) to form a polyvalent beta-lactosyl cluster. Coinjection of the trivalent (with C2 and C4 spacer arms) and polyvalent beta-lactosyl clusters with the highly metastatic B16 murine melanoma cells inhibited the formation of lung colonies in C57/BL mice, whereas the trivalent cluster with a C-9 spacer arm displayed no activity.

  DOI：

  10.1016/0008-6215(93)80071-l

文献信息

• Large-Scale Chemical and Enzymatic Synthesis of a<b> <i>Clostridium difficile</i> </b>Toxin A Binding Trisaccharide
  作者：R. Murray Ratcliffe、Monica M. Palcic、Vivekanand P. Kamath、Robert E. Yeske、Jonathan M. Gregson、Ying R. Fang

  DOI：10.1055/s-2004-831188

  日期：——

  Trisaccharide 1, 8-methoxycarbonyloctyl-O-(α-D-galactopyranosyl)-(1→3)-(β-D-galactopyranosyl)-(1→4)-β-D-glucopyranoside, linked to a solid support can be used to remove Clostridium difficile toxin A from the intestinal tract. Therefore, multi-gram chemical and enzymatic synthesis of the toxin binding trisaccharide 1 from 8-methoxycarbonyloctyl β-lactoside disaccharide 2 were explored. Chemical conversion

  三糖 1, 8-甲氧基羰基辛基-O-(α-D-吡喃半乳糖基)-(1→3)-(β-D-吡喃半乳糖基)-(1→4)-β-D-吡喃葡萄糖苷，连接到固体支持物上用于去除肠道中的艰难梭菌毒素 A。因此，探索了由 8-甲氧基羰基 β-乳糖苷二糖 2 合成毒素结合三糖 1 的多克化学和酶促合成方法。可通过七个步骤实现 30% 总产率的化学转化。或者，使用带有 UDP-半乳糖或 UDP-葡萄糖/UDP-Glc 差向异构酶的重组 α(1→3)-半乳糖基转移酶对乳糖苷进行单步酶促转化，得到 85-90% 产率的 1。
• Acceptor hydroxyl group mapping for calf thymus α-(1 → 3) - galactosyltransferase and enzymatic synthesis of α-d-Galp-(1 → 3)-β-d-Gal p-(1 → 4)-βd-GlcpNAc analogs
  作者：Keiko Sujino、Carles Malet、Ole Hindsgaul、Monica M. Palcic

  DOI：10.1016/s0008-6215(97)00268-1

  日期：1997.12

  Abstract The epitope of the acceptor substrate for α -(1 → 3)-galactosyltransferase from calf thymus has been mapped by using a series of mono-deoxygenated and mono- O -alkylated Type II (β- d - Gal p-(1 → 4)-β- d - Glc p NAc ) disaccharides. The 4-OH group of the β- d -galactopyranosyl residue is a key polar group essential for glycosyl transfer, tolerating neither deoxygenation nor O -alkylation

  摘要：利用一系列单脱氧和单-O-烷基化的II型（β-d-Galp-（1→ 4）-β-d-Glcp NAc）二糖。β-d-吡喃半乳糖基残基的4-OH基是糖基转移所必需的关键极性基团，既不耐受脱氧也不耐受O-烷基化。易于容许在6和6'位被各种极性烷基取代基取代，从而允许制备酶促合成一系列在每个羟基上带有极性取代基的三糖衍生物。这些新的类似物是艰难梭菌毒素A和人抗α-Gal抗体的潜在抑制剂。
• Sabesan, Subramaniam; Lemieux, Raymond U., Canadian Journal of Chemistry, 1984, vol. 62, p. 644 - 654
  作者：Sabesan, Subramaniam、Lemieux, Raymond U.

  DOI：——

  日期：——
• Substrate Recognition of the Membrane-Associated Sialidase NEU3 Requires a Hydrophobic Aglycone
  作者：Mahendra S. Sandbhor、Naoto Soya、Amgad Albohy、R. Blake Zheng、Jonathan Cartmell、David R. Bundle、John S. Klassen、Christopher W. Cairo

  DOI：10.1021/bi200449j

  日期：2011.8.16

  The human neuraminidases (NEU) consist of a family of four isoforms (NEU1-NEU4). Members of this enzyme family are proposed to have important roles in health and disease through regulation of the composition of cellular sialosides. The NEU3 isoform is a membrane-associated enzyme that cleaves glycolipid substrates. However, few reports have examined the substrate specificity of the enzyme for non-natural substrates. We report here a series of 11 synthetic trisaccharides that feature modifications of the aglycone or the Neu5Ac residue of an octyl beta-sialyllactoside. The time course of substrate cleavage by NEU3 was monitored using an electrospray ionization mass spectrometry assay to obtain relative rates (k(rel)). We observed that NEU3 substrate activity was directly dependent upon the hydrophobicity of the aglycone but had no apparent requirement for features of the ceramide headgroup. We also observed that trisaccharides with incorporated azide groups in the Neu5Ac residue at either C9 or the N5-Ac position were substrates, and in the case of the N5-azidoacetyl derivative, the activity was superior to that of GM3. However, the incorporation of larger aryl groups was tolerated only at C9, but not at N5-Ac. We propose a two-site model for enzyme recognition, requiring interaction at both the Neu5Ac residue and the hydrophobic aglycone.
• Large-scale chemical and chemo-enzymatic synthesis of a spacer-containing Pk-trisaccharide
  作者：Vivekanand P Kamath、Robert E Yeske、Jonathan M Gregson、R.Murray Ratcliffe、Ying R Fang、Monica M Palcic

  DOI：10.1016/j.carres.2003.12.027

  日期：2004.4

  The Pk-trisaccharide, linked to a solid carrier, is a potential agent for neutralization of shiga-like toxin in the gastrointestinal tract. Two approaches to the multigram-scale synthesis of a linkable Pk-trisaccharide derivative were therefore investigated. A four-step chemical synthesis yielded 8-methoxycarbonyloctyl beta-lactoside in 75% yield from lactose. Further conversion of this derivative through either multistep organic synthesis or one-step enzymatic galactosylation with UDP-galactose and recombinant alpha-1.4-Lyalactosyltransferase gave the Pk-trisaccharide derivative 8-methoxycarbonyloctyl alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl-(1-->4)-beta-D-glucopyranoside in 25% and 68% overall yields from commercial lactose, respectively. (C) 2004 Elsevier Ltd. All rights reserved.