Le^x | 71036-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Le^x
• 英文别名: Lewis X；3-Fucosyllactosamine；N-[(3R,4R,5S,6R)-2-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 71036-41-4
• 化学式: C₂₀H₃₅NO₁₅
• 分子量: 529.496
• InChiKey: HBBOZFUQJDYASD-QGTNPELVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  257
• 氢给体数：
  10
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Le^x 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 37.5h， 生成 N-(2-acetamido-2-deoxy-3-O-(α-L-fucopyranosyl)-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl)-N-((3-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-5-yl)thioureido)propyl)-O-methylhydroxylamine
  参考文献：
  名称：

  N-烷基-甲氧基胺双功能接头用于制备糖缀合物的多功能性。

  摘要：

  描述了N-糖基-N-烷基-甲氧基胺双功能接头在合成多种糖缀合物中的应用。接头含有特定的官能团，例如胺，叠氮化物，硫醇或羧酸，可用于偶联方法，包括酰胺连接，磺酰化，铜介导的惠斯根环加成或硫醇-马来酰亚胺偶联。以此方式，配备有生物素，荧光报道分子或蛋白质的糖缀合物被有效地合成，从而证明了这种类型的氧胺接头在糖缀合物探针的构建中的多功能性。

  DOI：

  10.1007/s10719-017-9785-4
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 反应 2.0h， 以2.8 mg的产率得到Le^x
  参考文献：
  名称：

  A new glycosylation method part 3: study of microwave effects at low temperatures to control reaction pathways and reduce byproducts

  摘要：

  The efficiency of microwave irradiation at low temperature for glycosylations is described. Although oligosaccharide synthesis usually requires reactive donors for glycosylations, which have leaving groups on the another positions, i.e., trichloroacetoimidates, halogenates, thioalkyl glycosides, etc., the suitable donors in our microwave supported synthesis of Lewis X oligosaccharide were very stable acetate derivatives. Regarding glycosylation with a fucosyl acetate donor and a glucosamine acceptor, microwave irradiation with simultaneous cooling improved yields. Moreover, further synthesis to Lewis X derivatives was achieved only with microwave irradiation at low temperatures. Without microwave irradiation, we could only obtain byproducts and none of the designed product at any reaction temperature. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.011

文献信息

• The modular synthesis of multivalent functionalised glycodendrons for the detection of lectins including DC-SIGN
  作者：Stefan Munneke、Kristel Kodar、Gavin F. Painter、Bridget L. Stocker、Mattie S. M. Timmer

  DOI：10.1039/c7ra08872h

  日期：——

  Glycodendrons are excellent tools for the biological evaluation of lectins. Herein, we present the expedient and efficient synthesis of a versatile second generation dendron scaffold using double exponential growth methodology. The dendron scaffold can be rapidly functionalised, as illustrated by the conjugation of the dendron scaffold to biotin or a fluorescent probe, followed by oxyamine glycan conjugation

  糖原龙是对凝集素进行生物学评估的极佳工具。在这里，我们提出了使用双指数增长方法的通用第二代树突支架的便捷有效的合成方法。树突支架可以快速功能化，如将树突支架缀合至生物素或荧光探针所示，然后将氧胺聚糖缀合至所选的聚糖。然后证明了荧光Lewis X糖树胶用于检测巨噬细胞上的C型凝集素DC-SIGN的用途。
• Characterization of<i>Helicobacter pylori</i>α1,2-Fucosyltransferase for Enzymatic Synthesis of Tumor-Associated Antigens
  作者：Daniel B. Stein、Yu-Nong Lin、Chun-Hung Lin

  DOI：10.1002/adsc.200800435

  日期：2008.10.6

  Helicobacter pylori catalyzes the fucosylation of acceptor oligosaccharides at the C2-OH of terminal Galβ units. The enzyme from strain NCTC11639 was evaluated for its ability to synthesize cancer-associated antigens. The α1,2-FucT was determined to be active over a pH range between 4.0 and 8.0 with the optimum occurring at pH 5.0. Although a divalent metal ion cofactor was not required for catalysis, enhancement

  来自幽门螺杆菌的α1,2-岩藻糖基转移酶（α1,2-FucT）催化末端Galβ单元的C2-OH上受体寡糖的岩藻糖基化。评价了来自菌株NCTC11639的酶合成癌症相关抗原的能力。经测定，α1,2-FucT在4.0至8.0的pH范围内具有活性，最适在pH 5.0时发生。尽管催化不需要二价金属离子辅助因子，但在添加Mn 2+后可检测到酶活性的增强。。详细的底物特异性分析表明，α1,2-FucT可以催化多种寡糖底物的岩藻糖基化。与包含2型结构（Galβ1-4GlcNAc）的聚糖相比，优选地，所述α1,2-FucT包含岩藻糖基化的1型结构（Galβ1-3GlcNAc）的聚糖。发现路易斯A三糖[Galβ1-3（Fucα1-4）GlcNAc]是最好的受体。唯一的例外是Lewis x五糖LNFP III [Galβ1-4（Fucα1-3）GlcNAcβ1-3Galβ1-4Glc]优于Lewis a类似物LNFP
• POLYVALENT BIOCONJUGATES
  申请人：Natunen Jari

  公开号：US20100093659A1

  公开（公告）日：2010-04-15

  The present invention is directed to conjugates for biorecognition comprising (i) an carbohydrate backbone structure (PO) of 5 to 20 monosaccharide units, (ii) oligosaccharide biorecognition groups (Bio) of 1 to 10 monomer units, (iii) a bifunctional spacer groups of the formula -(y)p-(S)q-(z)r-, wherein S is a spacer group, p, q and r are each 0 or 1, whereby at least one of p and r is different from 0, and y and z are chemoselective ligation groups, which covalently link a said Bio group to said backbone structure, and the degree of conjugation, indicating the average number of covalently attached Bio biorecognition groups per monomer unit of the backbone, being from 0.2 to 1. The invention is also directed to processes for their preparation, intermediates for use in the process as well as use of said conjugates, especially for inhibiting pathogenic bacteria.

  本发明涉及用于生物识别的共轭物，包括(i)由5至20个单糖单元组成的碳水化合物骨架结构（PO），(ii)由1至10个单体单元组成的寡糖生物识别基团（Bio），(iii)具有式子-(y)p-(S)q-(z)r-的双功能间隔基团，其中S是间隔基团，p、q和r分别为0或1，其中至少一个p和r不为0，y和z是化学选择性连接基团，将所述的Bio基团共价连接到所述的骨架结构上，而共轭度表示平均每个骨架单体单位上共价连接的Bio生物识别基团的数量为0.2至1。本发明还涉及其制备过程，用于该过程的中间体以及所述共轭物的用途，特别是用于抑制病原细菌。
• 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
• A cloned human cDNA determines expression of a mouse stage-specific embryonic antigen and the Lewis blood group alpha(1,3/1,4)fucosyltransferase.
  作者：J F Kukowska-Latallo、R D Larsen、R P Nair、J B Lowe

  DOI：10.1101/gad.4.8.1288

  日期：1990.8

  alpha(1,4)- and Fuc alpha(1,3)-linkages, respectively, in a manner analogous to the human Lewis blood group fucosyltransferase. Southern blot analysis shows that the cDNA corresponds to sequences syntenic to the Lewis locus on chromosome 19. These results indicate that this cDNA is the product of the human Lewis blood group locus, provide genetic confirmation of the hypothesis that this enzyme can catalyze

  阶段特异性胚胎抗原SSEA-1是一种细胞表面寡糖分子，在鼠的植入前期以时间精度表达，并参与涉及压紧过程的粘附事件。我们使用了哺乳动物瞬时表达系统来分离确定SSEA-1分子表达的克隆人cDNA。cDNA序列预测II型跨膜蛋白，其结构域结构类似于哺乳动物糖基转移酶，但与这些酶没有一级序列相似性。当在COS-1细胞中作为分泌的蛋白A融合肽的一部分表达时，该蛋白的羧基末端结构域作为岩藻糖基转移酶具有催化活性。该酶是一种特殊的糖基转移酶，因为它可以使用I型和II型寡糖作为受体底物，分别以类似于以下方式的方式生成亚端Fuc alpha（1,4）-和Fuc alpha（1,3）-连接。人类刘易斯血型岩藻糖基转移酶。Southern印迹分析表明该cDNA对应于与19号染色体Lewis位点同序的序列。这些结果表明该cDNA是人类Lewis血型位点的产物，为该酶可以催化两个不同的转糖基化的假设提供了遗传学证实