O-α-L-Fucopyranosyl-(1->2)-O-β-D-galactopyranosyl-(1->4)-O-<α-L-fucopyranosyl-(1->3)>-D-glucose | 34852-43-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-α-L-Fucopyranosyl-(1->2)-O-β-D-galactopyranosyl-(1->4)-O-<α-L-fucopyranosyl-(1->3)>-D-glucose
• 英文别名: α-L-Fuc-(1->2)-β-D-Gal-(1->4)-D-Glc-(3->1)-α-L-Fuc；2',3-difucosyllactose；lactodifucotetraose；difucosyllactose；Fuc(α1-2)Gal(β1-4)[Fuc(α1-3)]Glc；O-α-L-Fucopyranosyl-(1->2)-O-β-D-galactopyranosyl-(1->4)-O-[α-L-fucopyranosyl-(1->3)]-D-glucose；Fuc(a1-2)Gal(b1-4)[Fuc(a1-3)]Glc；(2S,3S,4R,5S,6S)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R)-5,6-dihydroxy-2-(hydroxymethyl)-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 34852-43-2；109959-08-2
• 化学式: C₂₄H₄₂O₁₉
• 分子量: 634.586
• InChiKey: LKOHREGGXUJGKC-NTQZDHPLSA-N

物化性质

• 沸点：
  930.8±65.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  307
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  Benzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-O-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->3)>-2-O-benzyl-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 72.0h， 以86%的产率得到O-α-L-Fucopyranosyl-(1->2)-O-β-D-galactopyranosyl-(1->4)-O-<α-L-fucopyranosyl-(1->3)>-D-glucose
  参考文献：
  名称：

  Synthesis of lactodifucotetraose

  摘要：

  DOI：

  10.1016/s0008-6215(00)90765-1

文献信息

• [EN] CRYSTALLINE DIFUCOSYLLACTOSE<br/>[FR] DIFUCOSYLLACTOSE CRISTALLIN
  申请人：GLYCOM AS

  公开号：WO2016086947A1

  公开（公告）日：2016-06-09

  Crystalline difucosyllactose, useful in a pharmaceutical composition and a nutritional composition is disclosed. Also disclosed is a method of obtaining crystalline difucosyllactose by crystallisation from a mixture of water and one or more C1 - C4 alcohols and a method of synthesising difucosyllactose from suitably protected lactose and a glycosyl donor.

  本发明揭示了结晶二岐糖乳酸，其在制药组合物和营养组合物中有用。还揭示了一种从水和一种或多种C1-C4醇的混合物中通过结晶获得结晶二岐糖乳酸的方法，以及从适当保护的乳糖和糖基供体合成二岐糖乳酸的方法。
• 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
• The cloning and expression of a human α-1,3 fucosyltransferase capable of forming the E-selectin ligand
  作者：Kari L. Koszdin、Benjamin R. Bowen

  DOI：10.1016/s0006-291x(05)81472-x

  日期：1992.8

  The polymerase chain reaction was used to amplify a novel fucosyltransferase cDNA (FucT-VI) from A431 and from HL60 cells. The amplified cDNA has a high degree of sequence identity to FucT-V and to FucT-III, and a much lower level of similarity to FucT-IV. Transfection of the FucT-VI gene into mammalian cells confers alpha-1,3 fucosyltransferase activity to the cells, resulting in cell surface expression of Lewis x and sialyl-Lewis x carbohydrates. In contrast to FucT-IV activity, FucT-VI catalyzes the transfer of fucose from GDP-beta-fucose to alpha-2,3 sialylated substrates. The substrate specificity of the FucT-VI gene product suggests that FucT-VI may be an enzyme involved in the biosynthesis of the E-Selectin ligand, sialyl-Lewis x, in myeloid cells.
• Synthesis of lactodifucotetraose
  作者：Ken'ichi Takeo、Saimei Tei

  DOI：10.1016/s0008-6215(00)90765-1

  日期：1985.8