methyl 8-{[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosamyl]oxy}nonanoate | 64160-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 8-{[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosamyl]oxy}nonanoate
• 英文别名: methyl 9-[(2R,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxynonanoate
• CAS: 64160-39-0
• 化学式: C₂₄H₄₃NO₁₃
• 分子量: 553.604
• InChiKey: QCWPROARBPOGDI-CYABAIRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  214
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 8-{[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosamyl]oxy}nonanoate 、 胞苷-5'-单磷酸-N-乙酰神经氨酸 在 bovine serum albumine 、 α(2-3)-(N)-sialyltransferase 、 calf intestine alkaline phosphatase 、 Na-cacodylate buffer 、 manganese(ll) chloride 作用下， 以 水 为溶剂， 以70%的产率得到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：

  Enzymatic α(2–3)sialylation of non-natural type-I (Lewisc) disaccharides with recombinant sialyl-transferase

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(97)10201-3
• 作为产物：
  描述：

  9-[(2R,3R,4R,5S,6R)-5-Acetoxy-6-acetoxymethyl-3-acetylamino-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 methyl 8-{[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosamyl]oxy}nonanoate
  参考文献：
  名称：

  Enzymatic α(2–3)sialylation of non-natural type-I (Lewisc) disaccharides with recombinant sialyl-transferase

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(97)10201-3

文献信息

• Chemical synthesis of GDP-fucose analogs and their utilization by the Lewis *A(1 → 4) fucosyltransferase
  作者：Uday B. Gokhale、Ole Hindsgaul、Monica M. Palcic

  DOI：10.1139/v90-165

  日期：1990.7.1

  Chemical syntheses are reported for GDP-fucose (5), GDP-3-deoxy-fucose (6), and GDP-arabinose (7), the demethyl analog of 5. All three sugar nucleotides were found to act as donor substrates for an α(1 → 4) fucosyltransferase isolated from human milk when *BDGal(1 → 3)*BDGlcNAc-O(CH₂)₈COOMe (1) was used as the acceptor. The rate of transfer of sugar residues to 1 was measured using a coupled spectrophotometric assay and was found to be 100% (5), 2.3% (6), and 5.9% (7). The product Le^a-active oligosaccharide analogs were identified by both an enzyme-linked immunosorbent assay (ELISA) and by ¹H NMR spectroscopy. Keywords: glycosyltransferase, oligosaccharide synthesis, sugar-nucleotide analog, ELISA assay, fucosyltransferase.

  报道了GDP-岩藻糖（5）、GDP-3-去氧岩藻糖（6）和GDP-阿拉伯糖（7）的化学合成，其中7是5的去甲基类似物。当以*BDGal(1 → 3)*BDGlcNAc-O(CH₂)₈COOMe (1)作为受体时，发现这三种糖核苷酸都能作为人乳中分离的α(1 → 4)岩藻糖基转移酶的供体底物。使用耦合分光光度法测量糖残基转移速率，发现对1的转移率分别为100%（5）、2.3%（6）和5.9%（7）。通过酶联免疫吸附试验（ELISA）和¹H NMR光谱法鉴定了产物Le^a-活性寡糖类似物。关键词：糖基转移酶、寡糖合成、糖核苷酸类似物、ELISA检测、岩藻糖基转移酶。
• Glycosyltransferases: An Efficient Tool for the Enzymatic Synthesis of Oligosaccharides and Derivatives as well as Mimetics Thereof
  作者：Said Rabbani、Oliver Schwardt、Beat Ernst

  DOI：10.2533/000942906777675047

  日期：——

  Research over the past two decades has uncovered numerous biological roles for carbohydrates, e.g. in cell adhesion processes, signal transduction, malignant transformation, or viral and bacterial cell-surface recognition. Carbohydrates and structural analogues thereof are therefore considered as potential new leads. Although the chemical synthesis of carbohydrates is well established, the preparation of particular oligosaccharides still remains a costly and cumbersome challenge. A complementary approach to the chemical synthesis is the use of enzymatic methods. The transfer of monosaccharide moieties to natural substrates, catalyzed by glycosyltransferases, exhibits excellent chemo-, regio- and stereoselectivity. In addition, enzymatic glycosylations permit the synthesis of carbohydrate derivatives and even carbohydrate mimetics. Our results reveal a remarkable synthetic potential of fucosyltransferases VI (EC 2.4.1.65) and III (EC 2.4.1.65), and ? (2?3)-sialyltransferase ST3Gal III (EC 2.4.99.6). Their use for the preparative synthesis of oligosaccharides and derivatives as well as mimetics thereof is demonstrated.

  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。
• 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。
• Acceptor Specificity of Different Length Constructs of Human Recombinant α1,3/4-Fucosyltransferases
  作者：Theodora de Vries、Cheryl A. Srnka、Monica M. Palcic、Stuart J. Swiedler、Dirk H. van den Eijnden、Bruce A. Macher

  DOI：10.1074/jbc.270.15.8712

  日期：1995.4

  activity toward glycoproteins, whereas chimeric Fuc-TIII and Fuc-TV had a decreased activity with glycosphingolipids, compared to the full-length enzymes. Unexpectedly, chimeric Fuc-TV exhibited a GDP-fucose hydrolyzing activity. In substrates with multiple acceptor sites, the preferred site of fucosylation was identified. Fuc-TIII and Fuc-TV catalyzed fucose transfer exclusively to OH-3 of glucose in

  在COS-7细胞中表达的重组全长，与膜结合的岩藻糖基转移酶的受体特异性以及α1,3-岩藻糖基转移酶（Fuc-T）III，Fuc-TIV和Fuc-的可溶性蛋白A嵌合形式电视被分析为各种寡糖，糖脂和糖蛋白底物。我们对全长酶的研究结果证实并扩展了先前的研究。然而，与全长酶相比，嵌合Fuc-Ts对糖蛋白的活性增加，而嵌合Fuc-TIII和Fuc-TV对糖鞘脂的活性却降低。出乎意料的是，嵌合的Fuc-TV表现出GDP-岩藻糖的水解活性。在具有多个受体位点的底物中，鉴定了岩藻糖基化的优选位点。1 H NMR光谱证实，Fuc-TIII和Fuc-TV分别催化将岩藻糖仅转移至乳糖N-新四糖和乳糖N-四糖中葡萄糖的OH-3上。薄层色谱免疫染色显示，FucT-IV首选nLc6Cer中的远端GlcNAc残基，而Fuc-TV则首选近端G1-cNAc残基。将Fuc-TIV或Fuc-TV与VI3NeuAcnLc6Cer
• Recognition of β-d-Gal p-(1 → 3)-β-d-Glc pNAc-OR acceptor analogues by the Lewis α-(1 → 34)-fucosyltransferase from human milk
  作者：Minghui Du、Ole Hindsgaul

  DOI：10.1016/0008-6215(96)00047-x

  日期：1996.6

  The Lewis alpha-(1 --> 3/4)-frucosyltransferase (E.C. 2.4.1.65) transfers L-fucose from GDP-fucose to OH-4 of the Glc pNAc residue in the disaccharide beta-D-Gal p-(1 --> 3)-beta-D-Glc pNAc-OR [R = (CH2)(8)COOMe] (1) to give the Lewis-A blood group determinant beta-D-Gal p-(1 --> 3)-[alpha-L-Fuc p-(1 --> 4)]-beta-D-Glc pNAc-OR. Five deoxy analogues of 1, as well as its N-propionyl derivative, were chemically synthesized and kinetically evaluated as both substrates and inhibitors for the enzyme from human milk. The unmodified acceptor 1 had K-m = 640 mu M with V-max set arbitrarily to 100. The 6-deoxy (K-m = 400 mu M, V-max = 90) and N-propionyl compounds (K-m = 330 mu M, V-max = 170) remained excellent substrates while the 4-deoxy compound was a very weak competitive inhibitor with K-i = 9 mM. Deoxygenation of OH-2' and OH-4' (of the Gal residue) in 1 had little effect on the activity. The OH-6 group of the Gal residue proved to be critical for recognition by the enzyme since substitution of this group with hydrogen led to an inactive compound. (C) 1996 Elsevier Science Ltd.