6-Aminohexyl O-(β-D-galactopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside | 72358-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Aminohexyl O-(β-D-galactopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: 6-aminohexyl-O-[2-deoxy-2-acetamido-4-O-(β-D-galactopyranosyl)]-β-D-glucopyranoside；N-[(2R,3R,4R,5S,6R)-2-(6-aminohexoxy)-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 72358-27-1
• 化学式: C₂₀H₃₈N₂O₁₁
• 分子量: 482.529
• InChiKey: FJQAZUAMQKVXIC-KDKNCOTBSA-N

物化性质

• 沸点：
  799.0±60.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  213
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  6-Aminohexyl O-(β-D-galactopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside 在 sodium cacodylate 、 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 258.0h， 生成 6-(3-Fluoresceinylthioureido)hexyl O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-(β-D-galactopyranosyl)-(1->4)-O-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  荧光标记的受体对唾液酸转移酶的新测定

  摘要：

  描述了基于荧光素标记的受体寡糖的用于唾液酸转移酶活性的新型HPLC测定系统。荧光素标记的二糖βGal-（14）-βGlcNAc-OR（4），βGal-（14）-βGlcNAc-OR（17）和βGal-（13）-βGlcNAc-OR（22），其中OR包含六个合成了附着有荧光素的碳间隔基。以制备规模化学酶法生产合成标准产物，以产生荧光素标记的三糖。通过使用反相HPLC和离子对试剂，可以从产物中分离出原料，并分离出两种同分异构的三糖αNeu5Ac-（23/6）-βGal-（14）-βGlcNAc-OR（24和25），因此该测定法可用于测量混合物中不同的甲硅烷基转移酶活性。该测定法成功地用于检测市售酶和牛初乳的粗制品的唾液酸转移酶活性。牛初乳中主要的唾液酸转移酶活性将唾液酸α（2–6）添加到17中。

  DOI：

  10.1002/jlac.199619961111
• 作为产物：
  描述：

  6-叠氮基-1-己醇 在 钯 甲酸 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 32.2h， 生成 6-Aminohexyl O-(β-D-galactopyranosyl)-(1->4)-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

• Recombinant (2→3)-α-sialyltransferase immobilized on nickel-Agarose for preparative synthesis of sialyl Lewisx and Lewisa precursor oligosaccharides
  作者：Tatiana Ivannikova、Fabrice Bintein、Annie Malleron、Sylvie Juliant、Martine Cerutti、Anne Harduin-Lepers、Philippe Delannoy、Claudine Augé、André Lubineau

  DOI：10.1016/s0008-6215(03)00130-7

  日期：2003.5

  Ac-O-CH(2)](2)-C-(CH(2)OBn)(2) (12); (ii) the dansylated derivative, alpha-Neu5Ac-(2-->3)-D-Galp-(1-->3)-beta-D-GlcpNAc-O-(CH(2))(6)-NH-dansyl and; (iii) the tetrasacharide alpha-Neu5Ac-(2-->3)-beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->2)-alpha-D-Manp-O-CH(3). Compound 12 was itself prepared from the divalent N-acetyllactosamine molecule built on pentaerythritol by a chemo-enzymatic route.

  在杆状病毒感染的昆虫细胞中表达的重组（2-> 3）-α-唾液酸转移酶（ST3Gal-III）的特异性已通过各种寡糖受体和糖核苷酸供体进行了基于荧光的测定。标记有多组氨酸尾巴的重组ST3Gal-III被固定在Ni（2 +）-NTA-琼脂糖上，作为活性酶用于合成三种唾液酸化寡糖：（i）二价分子[α-Neu5Ac-（2-- > 3）-D-Galp-（1-> 4）-beta-D-GlcpNAc-O-CH（2）]（2）-C-（CH（2）OBn）（2）（12）；（ii）丹磺化衍生物α-Neu5Ac-（2-> 3）-D-Galp-（1-> 3）-β-D-GlcpNAc-O-（CH（2））（6）-NH -丹磺酰基和；（iii）四糖α-Neu5Ac-（2-> 3）-β-D-Galp-（1→4）-β-D-GlcpNAc-（1→2）-α-D-Manp -O-CH（3）。
• Outstanding stability of immobilized recombinant α(1→3/4)-fucosyltransferases exploited in the synthesis of Lewis a and Lewis x trisaccharides
  作者：Claudine Augé、Annie Malleron、André Lubineau、Halima Tahrat、Annie Marc、Jean-Louis Goergen、Martine Cerutti、Wim F. A. Steelant、Philippe Delannoy

  DOI：10.1039/b006063l

  日期：——

  Recombinant human α(1→3/4)-fucosyltransferases (FucT-III) expressed in CHO cells or baculovirus-infected insect cells, immobilized on Ni2+-agarose through a 6His tag, exhibit a marked stability, which was exploited in the synthesis of Lewis a and Lewis x trisaccharides.

  重组人α(1→3/4)-岩藻糖基转移酶（FucT-III）在CHO细胞或被 baculovirus 感染的昆虫细胞中表达，通过6His标签固定在Ni2+-琼脂糖上，表现出显著的稳定性，这在Lewis a和Lewis x 三糖的合成中得到了利用。
• 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.
• A New Assay For Sialyltransferases Using Fluorescein-Labelled Acceptors
  作者：Gerrit Limberg、George C. Slim、Richard H. Furneaux、Catharine A. Compston、Peter Stangier、Monica M. Palcic

  DOI：10.1002/jlac.199619961111

  日期：1996.11

  disaccharides βGal-(14)-βGlc-OR (4), βGal-(14)-βGlcNAc-OR (17), and βGal-(13)-βGlcNAc-OR (22) where OR consists of a six carbon spacer with fluorescein attached, were synthesised. Synthetic standard products were produced chemo-enzymatically on a preparative scale to yield fluorescein-labelled trisaccharides. The use of reverse phase HPLC with an ionpairing agent allowed the separation of starting materials

  描述了基于荧光素标记的受体寡糖的用于唾液酸转移酶活性的新型HPLC测定系统。荧光素标记的二糖βGal-（14）-βGlcNAc-OR（4），βGal-（14）-βGlcNAc-OR（17）和βGal-（13）-βGlcNAc-OR（22），其中OR包含六个合成了附着有荧光素的碳间隔基。以制备规模化学酶法生产合成标准产物，以产生荧光素标记的三糖。通过使用反相HPLC和离子对试剂，可以从产物中分离出原料，并分离出两种同分异构的三糖αNeu5Ac-（23/6）-βGal-（14）-βGlcNAc-OR（24和25），因此该测定法可用于测量混合物中不同的甲硅烷基转移酶活性。该测定法成功地用于检测市售酶和牛初乳的粗制品的唾液酸转移酶活性。牛初乳中主要的唾液酸转移酶活性将唾液酸α（2–6）添加到17中。