8-(methoxycarbonyl)octyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside | 122290-69-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-(methoxycarbonyl)octyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: (2S,4S,5R,6R)-5-acetamido-2-[(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-(9-methoxy-9-oxononoxy)oxan-4-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: 122290-69-1
• 化学式: C₃₅H₆₀N₂O₂₁
• 分子量: 844.862
• InChiKey: SHEDRPLGXZDJOE-VIXPEKPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  58
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  359
• 氢给体数：
  12
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  8-(methoxycarbonyl)octyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside 、 5`-二磷酸鸟嘌呤核苷-岩藻糖二钠盐 在 苯磺酰胺 、 H. pylori α(1->4) fucosyltransferase 、 manganese(ll) chloride 作用下， 以 various solvent(s) 为溶剂， 反应 0.5h， 生成 (2S,4S,5R,6R)-5-acetamido-2-[(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetamido-2-(hydroxymethyl)-6-(9-methoxy-9-oxononoxy)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  Glycosyltransferases: An Efficient Tool for the Enzymatic Synthesis of Oligosaccharides and Derivatives as well as Mimetics Thereof

  摘要：

  过去20年的研究揭示了碳水化合物在许多生物学过程中的作用，例如在细胞黏附过程、信号转导、恶性转化或病毒和细菌细胞表面识别中的作用。因此，碳水化合物及其结构类似物被认为是潜在的新线索。虽然碳水化合物的化学合成已经得到了很好的建立，但特定寡糖的制备仍然是一项昂贵而繁琐的挑战。化学合成的补充方法是使用酶法。由糖基转移酶催化的单糖基团转移到天然底物上，具有出色的化学、区域和立体选择性。此外，酶促糖基化允许合成碳水化合物衍生物甚至类似物。我们的研究结果显示，岩藻糖转移酶VI（EC 2.4.1.65）和III（EC 2.4.1.65），以及（2-3）-唾液酸转移酶ST3Gal III（EC 2.4.99.6）具有显著的合成潜力。我们演示了它们在制备寡糖及其衍生物和类似物方面的应用。

  DOI：

  10.2533/000942906777675047
• 作为产物：
  描述：

  8-(methoxycarbonyl)octyl O-(benzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2<*>3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-6-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside 在 palladium on activated charcoal 吡啶 、 硫化氢 、 氢气 、 sodium methylate 、 三乙胺 作用下， 以 水 为溶剂， 反应 16.0h， 生成 8-(methoxycarbonyl)octyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  人乳岩藻糖基转移酶在化学酶法合成在还原单元C-2位置修饰的唾液酸Lewis（a）和唾液酸Lewis（x）四糖类似物的化学酶促合成中。

  摘要：

  两个系列的三糖，具有式α-Neu5Ac-（2-> 3）-β-D-Gal-（1→4）-β-D-GlcZ-OR和α-Neu5Ac-（2-- > 3）-β-D-Gal-（1-> 3）-β-D-GlcZ-OR[R =（CH2）8CO2CH3]，其中2-脱氧取代基Z为叠氮基，氨基，丙酰胺基，或乙酰氨基，是通过化学合成制备的。两种类型的修饰的三糖都是获自人乳的岩藻糖基转移酶制剂的受体。使用该酶进行的岩藻糖基化制备提供了唾液酸化的Lewis（x）和唾液酸化的Lewis（a）四糖结构的类似物，它们被认为是细胞粘附分子的配体。这些合成进一步证明了糖基转移酶在寡糖类似物的制备中的用途。

  DOI：

  10.1016/0008-6215(93)84162-y

文献信息

• Enzymic synthesis of oligosaccharides terminating in the tumor-associated sialyl-Lewis-a determinant
  作者：Monica M. Palcic、André P. Venot、R.Murray Ratcliffe、Ole Hindsgaul

  DOI：10.1016/0008-6215(89)84141-2

  日期：1989.7

  The isomeric sialyl-Lea-terminating pentasaccharide derivatives, alpha-Neup5Ac-(2----3)-beta-D-Galp-(1----3)-[alpha-L-Fucp-(1 ----4)]-beta- D-GlcpNAc-(1----3)-beta-D-Galp-O(CH2)8COOMe and alpha-Neup5Ac-(2----3)-beta-D-Galp-(1----3)-[alpha-L-Fucp-(1 ----4)]- beta-D-GlcpNAc-(1----6)-beta-D-Galp-O(CH2)8COOMe, have been prepared by the action in sequence of a porcine submaxillary (2----3)-alpha-sialyltransferase

  异构的唾液酸-Lea-末端五糖衍生物，α-Neup5Ac-（2 ---- 3）-β-D-Galp-（1 ---- 3）-[α-L-Fucp-（1- -4）]-beta- D-GlcpNAc-（1 ---- 3）-beta-D-Galp-O（CH2）8COOMe和alpha-Neup5Ac-（2 ---- 3）-beta-D-Galp -（1 ---- 3）-[alpha-L-Fucp-（1 ---- 4）]-beta-D-GlcpNAc-（1 ---- 6）-beta-D-Galp-O（ CH2）8COOMe是通过猪上颌（2 ---- 3）-α-唾液酸转移酶和人乳（1 ----- 3/4）-α-岩藻糖基转移酶的顺序作用而制备的合成的三糖β-D-Galp-（1 ---- 3）-β-D-GlcpNAc-（1 ---- 3）-和-（1 ---- 6）-β-D-Galp-O （CH2）8COOMe。
• Substrate Specificity and Preparative Use of Recombinant Rat ST3Gal III
  作者：Oliver Schwardt、Gan‐Pan Gao、Tamara Visekruna、Said Rabbani、Ernst Gassmann、Beat Ernst

  DOI：10.1081/car-120030021

  日期：2004.12.26

  Recombinant rat alpha(2-->3)-sialyltransferase (ST3Gal III, EC 2.4.99.6) was expressed from baculovirus infected Sf 9 insect cells in preparative amounts. In order to elucidate substrate tolerances of ST3Gal III, the natural type I and type II substrates 21 and 22 as well as several non-natural sugars were investigated. The non-natural Gal-beta(1 --> 3)Gal-(N) (type III) disaccharides 11, 13, and 16 turned out to be surprisingly good substrates for ST3Gal III. All sialylations were run in preparative scale and kinetic parameters (V-max and K-m) were determined.
• Enzymatic α(2–3)sialylation of non-natural type-I (Lewisc) disaccharides with recombinant sialyl-transferase
  作者：Gabi Baisch、Reinhold Öhrlein、Markus Streiff

  DOI：10.1016/s0960-894x(97)10201-3

  日期：1998.1

  Recombinant alpha(2-3)sialyl-transferase from rat liver is used to sialylate a series of type-I (Lewis(c)) disaccharides on a preparative scale. The enzyme tolerates a broad array of N-acetyl replacements of the N-glucosamine subunit ranging from small and large lipophilic groups to charged and heterocyclic amides. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Enzymatic fucosylations of non-natural sialylated type-I trisaccharides with recombinant fucosyl-transferase-III
  作者：Gabi Baisch、Reinhold Öhrlein、Markus Streiff

  DOI：10.1016/s0960-894x(97)10202-5

  日期：1998.1

  Recombinant fucosyl-transferase-III (Lewis type enzyme) is used to prepare a series of non-natural sialyl-Lewis(a) derivatives on a preparative scale. The enzyme tolerates a wide range of accepters which have the natural N-acetyl group of the glucosamine moiety replaced by substituted aromatic and heteroaromatic amides. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Use of human-milk fucosyltransferase in the chemoenzymic synthesis of analogues of the sialyl Lewis and sialyl Lewis tetrasaccharides modified at the C-2 position of the reducing unit
  作者：Pandurang V. Nikrad、Mohammed A. Kashem、Kenneth B. Wlasichuk、Gordon Alton、Andre P. Venot

  DOI：10.1016/0008-6215(93)84162-y

  日期：1993.12

  2-deoxy substituent Z is azido, amino, propionamido, or acetamido, were prepared by chemical synthesis. Both types of modified trisaccharides are acceptors for a fucosyltransferase preparation obtained from human milk. Preparative fucosylations using this enzyme provided analogues of the sialyl Lewis(x) and sialyl Lewis(a) tetrasaccharide structures, which have been proposed to be ligands for cell-adhesion

  两个系列的三糖，具有式α-Neu5Ac-（2-> 3）-β-D-Gal-（1→4）-β-D-GlcZ-OR和α-Neu5Ac-（2-- > 3）-β-D-Gal-（1-> 3）-β-D-GlcZ-OR[R =（CH2）8CO2CH3]，其中2-脱氧取代基Z为叠氮基，氨基，丙酰胺基，或乙酰氨基，是通过化学合成制备的。两种类型的修饰的三糖都是获自人乳的岩藻糖基转移酶制剂的受体。使用该酶进行的岩藻糖基化制备提供了唾液酸化的Lewis（x）和唾液酸化的Lewis（a）四糖结构的类似物，它们被认为是细胞粘附分子的配体。这些合成进一步证明了糖基转移酶在寡糖类似物的制备中的用途。