octyl α-L-fucopyranosyl-(1->2)-β-D-galactopyranoside | 155300-75-7

• 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: octyl α-L-fucopyranosyl-(1->2)-β-D-galactopyranoside
• 英文别名: α-L-Fuc-(1-> 2)-Gal-β-D-O-(CH2)7CH3；octyl 2-O-(α-L-fucopyranosyl)-β-D-galactopyranoside；α-L-fuc-(1->2)-β-D-gal-O-octyl；α-Fuc-(1->2)-β-D-Gal-O(CH2)7CH3；Fucα1-2Galβ-O-(CH2)7CH3；Octyl 2-O-(6-Deoxy-Alpha-L-Galactopyranosyl)-Beta-D-Galactopyranoside；(2S,3S,4R,5S,6S)-2-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-octoxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 155300-75-7
• 化学式: C₂₀H₃₈O₁₀
• 分子量: 438.516
• InChiKey: GTTDTLMUWQMDNA-ARNYJBIMSA-N

物化性质

• 沸点：
  631.2±55.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 octyl α-L-fucopyranosyl-(1->2)-β-D-galactopyranoside 在 glycosyltransferase B 、 sodium cacodylate 、 alkaline phosphatase 作用下， 以 水 为溶剂， 反应 504.0h， 以98%的产率得到α-D-Glcp-(1-> 3)-[α-L-Fucp-(1-> 2)]-β-D-Galp-O-(CH2)7CH3
  参考文献：
  名称：

  血型A和B三糖类似物的酶促合成。

  摘要：

  糖基转移酶A和B在通过O（H）受体底物生物合成人血A和B组三糖抗原时分别利用供体底物UDP-GalNAc和UDP-Gal。这些酶被克隆为合成基因，并在大肠杆菌中表达，从而产生了大量用于供体特异性评估的酶。糖基转移酶A的氨基酸序列与糖基转移酶B的区别仅在于四个氨基酸，这四个氨基酸残基的改变（Arg-176-> Gly，Gly-235-> Ser，Leu-266-> Met和Gly-268-> Ala）可以将供体底物特异性从UDP-GalNAc更改为UDP-Gal。已经观察到供体底物特异性的交叉，即，A转移酶可以利用UDP-Gal，而B转移酶可以利用UDP-GalNAc供体底物。现在，我们报告每种酶类型的独特供体特异性。只有一种转移酶才能利用UDP-GlcNAc供体底物合成血型A三糖类似物α-D-Glcp-NAc-（1-> 3）-[α-L-Fucp-（1-> 2）]-β -D-Galp-O-（CH

  DOI：

  10.1016/s0008-6215(99)00297-9
• 作为产物：
  描述：

  辛醇 在 palladium on activated charcoal molecular sieve 、 hafnocene bistrifluoromethanesulfonate 、 氢气 作用下， 以 溶剂黄146 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 16.0h， 生成 octyl α-L-fucopyranosyl-(1->2)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a library of fucopyranosyl-galactopyranosides consisting of a complete set of anomeric configurations and linkage positions

  摘要：

  A library composed of a complete set of fucopyranosyl-galactopyranosides was synthesized. A perbenzylated phenylthio fucopyranoside and a series of tri-O-benzyl-galactopyranosyl fluorides having single hydroxyl groups at the 2-, 3-, 4-, and 6-positions were used as the glycosyl donor and glycosyl acceptors, respectively. The chosen set of functionalities at the anomeric centers enabled rapid access to the oligosaccharides based on chemoselective activation. The first coupling reaction was achieved by the action of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST). The resulting disaccharide fluoride was readily activated by hafnocene bistrifluoromethanesulfonate [Cp2Hf(OTf)(2)] and glycosidated with n-octanol. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.040

文献信息

• Recognition of synthetic deoxy and deoxyfluoro analogs of the acceptor α-l-Fucp-(1 → 2)-β-d-Galp-OR by the blood-group A and B gene-specified glycosyltransferases
  作者：Todd L. Lowary、Ole Hindsgaul

  DOI：10.1016/0008-6215(93)84068-h

  日期：1993.10

  Abstract The disaccharide α- l -Fuc p -O-(CH 2 ) 7 CH 3 (6) , is an acceptor for both glycosyltransferases responsible for the biosynthesis of the A and B blood-group antigens. These enzymes transfer GalNAc and Gal, respectively, with an α-linkage to OH-3 of the Gal residue in 6 . All six possible deoxy and deoxyfluoro analogs of 6 , with modifications on the target Gal residue, were chemically synthesized

  摘要二糖α-1-Fucp -O-（CH 2）7 CH 3（6）是负责A和B血型抗原生物合成的两个糖基转移酶的受体。这些酶分别将GalNAc和Gal转移至6中Gal残基的OH-3上，且具有α键。化学合成了6种在目标Gal残基上有修饰的6种可能的6种脱氧和脱氧氟类似物，并进行了动力学评估，作为A和B糖基转移酶的底物和抑制剂。两种酶都将耐受Gal残基的3和6位羟基的取代。但是，Gal残基的OH-4取代取代了这些糖基转移酶的识别。6脱氧和6氟化合物是这两种酶的底物，而3脱氧和3氟化合物是竞争性抑制剂，K i值在14–110μM范围内。已经确定了6-脱氧和6-氟衍生物的动力学常数。
• Chemoenzymatic Synthesis of α-(1→3)-Gal(NAc)-Terminating Glycosides of Complex Tertiary Sugar Alcohols
  作者：Xiangping Qian、Keiko Sujino、Albin Otter、Monica M. Palcic、Ole Hindsgaul

  DOI：10.1021/ja993004g

  日期：1999.12.1

  analogues in which the ring carbon bearing the OH groups undergoing enzymatic glycosylation in the natural reactions had their C−H bond replaced with a C-methyl or C-propyl bond. The tertiary C-methyl alcohols proved to be kinetically competent substrates which permitted the enzymatic preparation of the expected product trisaccharides in near quantitative yields.

  糖基转移酶在寡糖类似物合成中的范围已扩大到包括使用“保留”酶作用于复杂的三级 C 支链二糖受体。研究的酶是α1,3-半乳糖基转移酶（α1,3-GalT，EC 2.4.1.151），它使用Galβ1→4Glcβ-OR作为受体，以及重组血型A [α1,3-GalNAc转移酶（GTA），EC 2.4.1.40] 和 B [α1,3-Gal 转移酶 (GTB), EC 2.4.1.37] 糖基转移酶，在其生物合成反应中使用 Fucα1→2Galβ-OR 作为受体。化学合成产生了受体类似物，其中在自然反应中进行酶促糖基化的带有 OH 基团的环碳的 C-H 键被 C-甲基或 C-丙基键取代。
• Orthogonal Glycosylation Reactions on Solid Phase and Synthesis of a Library Consisting of a Complete Set of Fucosyl Galactose Isomers
  作者：Osamu Kanie、Isao Ohtsuka、Takuro Ako、Shusaku Daikoku、Yoshimi Kanie、Rumiko Kato

  DOI：10.1002/anie.200600433

  日期：2006.6.2
• Enzymatic Synthesis of Oligosaccharide Analogues:  Evaluation of UDP-Gal Analogues as Donors for Three Retaining α-Galactosyltransferases
  作者：Keiko Sujino、Taketo Uchiyama、Ole Hindsgaul、Nina O. L. Seto、Warren W. Wakarchuk、Monica M. Palcic

  DOI：10.1021/ja990964u

  日期：2000.2.1

  A series of deoxygenated uridine 5'-diphosphogalactose (UDP-Gal) derivatives are evaluated as donors for three different retaining galactosyltransferases using capillary electrophoresis with laser-induced fluorescence detection. The enzymes investigated were calf thymus alpha(1-->3) galactosyltransferase (E.C. 2.4.1.151), blood group B alpha(1-->3) galactosyltransferase (E.C. 2.4.1.37) and Neisseria meningitidis alpha(1-->4) galactosyltransferase. UDP-2-deoxy-Gal and UDP-6-deoxy-Gal were found to be active as donors for all three enzymes. Preparative syntheses utilizing these UDP-Gal derivatives were performed on mg scales, affording deoxygenated trisaccharide analogues in 5-100% yields.
• Synthesis of a library of fucopyranosyl-galactopyranosides consisting of a complete set of anomeric configurations and linkage positions
  作者：Isao Ohtsuka、Takuro Ako、Rumiko Kato、Shusaku Daikoku、Satomi Koroghi、Takuya Kanemitsu、Osamu Kanie

  DOI：10.1016/j.carres.2006.03.040

  日期：2006.7

  A library composed of a complete set of fucopyranosyl-galactopyranosides was synthesized. A perbenzylated phenylthio fucopyranoside and a series of tri-O-benzyl-galactopyranosyl fluorides having single hydroxyl groups at the 2-, 3-, 4-, and 6-positions were used as the glycosyl donor and glycosyl acceptors, respectively. The chosen set of functionalities at the anomeric centers enabled rapid access to the oligosaccharides based on chemoselective activation. The first coupling reaction was achieved by the action of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST). The resulting disaccharide fluoride was readily activated by hafnocene bistrifluoromethanesulfonate [Cp2Hf(OTf)(2)] and glycosidated with n-octanol. (c) 2006 Elsevier Ltd. All rights reserved.