β-L-fucopyranose | 13224-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-L-fucopyranose
• 英文别名: β-L-Fucofuranose；α-L-fucose；β-L-fucose；L-fucose；6-deoxy-L-galactose；L-6-deoxy-galactose；beta-L-fucopyranose；(2S,3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol
• CAS: 13224-93-6
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: SHZGCJCMOBCMKK-KGJVWPDLSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  140 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  β-L-fucopyranose 在 fucose kinase 、 adenosine 5'-triphosphate disodium salt 作用下， 生成 6-脱氧-beta-L-半乳糖 1-磷酸酯
  参考文献：
  名称：

  Biochemical characterization of GDP-l-fucose de novo synthesis pathway in fungus Mortierella alpina

  摘要：

  Mortierella alpina is a filamentous fungus commonly found in soil, which is able to produce large amount of polyunsaturated fatty acids. L-Fucose is an important sugar found in a diverse range of organisms, playing a variety of biological roles. In this study, we characterized the de novo biosynthetic pathway of GDP-L-fucose (the nucleotide-activated form of L-fucose) in M. alpina. Genes encoding GDP-D-mannose 4,6-dehydratase (GMD) and GDP-keto-6-deoxymannose 3,5-epimerase/4-reductase (GMER) were expressed heterologously in Escherichia coli. The recombinant enzymes were produced as His-tagged fusion proteins. Conversion of GDP-mannose to GDP-4-keto-6-deoxy mannose by GMD and GDP-4-keto-6-deoxy mannose to GDP-L-fucose by GMER were analyzed by capillary electrophoresis, electro-spray ionization-mass spectrometry, and nuclear magnetic resonance spectroscopy. The k(m) values of GMD for GDP-mannose and GMER for GDP-4-keto-6-deoxy mannose were determined to be 0.77 mM and 1.047 mM, respectively. Both NADH and NADPH may be used by GMER as the coenzyme. The optimum temperature and pH were determined to be 37 degrees C and pH 9.0 (GMD) or pH 7.0 (GMER). Divalent cations are not required for GMD and GMER activity, and the activities of both enzymes may be enhanced by DTT. To our knowledge this is the first report on the characterization of GDP-L-fucose biosynthetic pathway in fungi. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bbrc.2009.12.116
• 作为产物：
  描述：

  (4S,5R)-4-[(R)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-((S)-1-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane 在 palladium on activated charcoal sodium periodate 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 β-L-fucopyranose
  参考文献：
  名称：

  由D-甘露糖合成L-岩藻糖及其类似物的简短方法

  摘要：

  描述了仅六步就从D-甘露糖合成L-岩藻糖（和6-烷基类似物）的新有效方法。这种转化是基于向D-甘露糖的双丙酮化物中添加有机金属试剂，然后用高碘酸钠选择性裂解乙二醇。还必须注意非对映异构体二苯甲酸酯的有效分离和2,5-二苄基（或苯甲酰基）-L-呋喃呋喃糖衍生物的形成。

  DOI：

  10.1016/s0040-4039(00)92522-x

文献信息

• Simple syntheses of L-fucopyranose and fucosidase inhibitors utilizing the highly stereoselective methylation of an arabinofuranoside 5-urose derivative
  作者：Shunya Takahashi、Hiroyoshi Kuzuhara

  DOI：10.1039/a606564c

  日期：——

  The simple syntheses of L-fucopyranose 1 and its three analogues 2–4 are described. A key reaction is a stereocontrolled elongation by one carbon unit at the side chain of an α-D-arabino-pentodialdo-1,4-furanoside 9 with MeMgI–ZnCl2 or Me3Al. Diastereofacial selectivities of more than 92% were achieved.

  简单报道了L-岩藻吡喃糖1及其三种类似物2-4的合成方法。关键反应是用MeMgI-ZnCl2或Me3Al在α-D-阿拉伯吡喃型戊二醛-1,4-呋喃糖9的侧链上进行立体控制的碳链延长一碳单位的反应。得到的手性面选择性超过92%。
• Use Of An Alkyl Glycoside Or Of A Mixture Of At Least Two Alkyl Glycosides As Agent Intended For Inhibiting Microbial Growth, And Compositions Containing It
  申请人：Thiebault Nicolas

  公开号：US20090306011A1

  公开（公告）日：2009-12-10

  The present invention relates to the use of an alkyl glycoside or of a mixture of at least two alkyl glycosides as agent intended for inhibiting microbial growth, in particular in a cosmetic, pharmaceutical or food composition.

  本发明涉及将烷基糖苷或至少两种烷基糖苷混合物用作抑制微生物生长的药剂，特别是在化妆品、药品或食品组合物中的用途。
• Synthesis of sugar-containing polymers by self-condensation with diboronic acid
  作者：Masafumi Mikami、Seiji Shinkai

  DOI：10.1039/c39950000153

  日期：——

  Self-condensation of 3,3′-bis(N,N-di-n-butylaminomethyl)biphenyl-4,4′-diboronic acid and saccharides yields polymers containing saccharides in the main chain: they show unique CD spectroscopic properties which reflect the chirality of saccharides.

  3,3′-双（N,N-二正丁基氨基甲基）联苯-4,4′-二硼酸与糖类的自缩合产生了主链中含有糖类的聚合物：它们显示出独特的 CD 光谱特性，反映了糖类的手性。
• Saccharide derivatives
  申请人：Synsorb Biotech, Inc.

  公开号：US06087339A1

  公开（公告）日：2000-07-11

  Disclosed are novel saccharide derivatives which inhibit binding of toxins, such as heat-labile enterotoxin or cholera toxin, to their receptors either in vitro or in vivo. Additionally, disclosed are compounds which inhibit binding of enterovirulent organisms (e.g., bacteria, virus, fungi, and the like), such as Vibrio cholerae and enterotoxigenic strains of Escherichia coli, to their cell surface receptors.

  本发明涉及一种新型糖衍生物，其可以在体外或体内抑制毒素（如热敏性肠毒素或霍乱毒素）与其受体的结合。此外，本发明还涉及一种化合物，其可以抑制肠道致病微生物（如细菌、病毒、真菌等）与其细胞表面受体的结合，例如霍乱弧菌和肠毒素原性大肠杆菌菌株。
• Methods and products for the synthesis of oligosaccharide structures on glycoproteins, glycolipids, or as free molecules, and for the isolation of cloned genetic sequences that determine these structures
  申请人：The Regents of the University of Michigan

  公开号：US20020102688A1

  公开（公告）日：2002-08-01

  A method for isolating a gene, comprising: (i) isolating a cell possessing a post-translational characteristic of interest, said post-translational characteristic being the presence of a membrane-bound oligosaccharide or polysaccharide of interest on the surface of said cell, the presence of a soluble oligosaccharide or polysaccharide of interest in an extract of said cell, or the presence of a particularly glycosyltransferase activity in an extract of said cell; (ii) creating a genetic library of either cDNA or genomic DNA from the genetic material of said isolated cell; (iii) transforming host cells with said genetic library; and (iv) screening said transformed host cells for a host cell containing said post-translational characteristic, thereby obtaining a cell containing said gene, is disclosed. The method can be used to obtain genes encoding glycosyltransferases.

  一种分离基因的方法，包括：（i）分离具有感兴趣的后翻译特征的细胞，该后翻译特征是感兴趣的膜结合寡糖或多糖在该细胞表面的存在，感兴趣的寡糖或多糖在该细胞提取物中的存在，或者在该细胞提取物中具有特定的糖基转移酶活性；（ii）从所分离的细胞的遗传物质中创建cDNA或基因组DNA的基因库；（iii）将宿主细胞转化为该基因库；和（iv）筛选所转化的宿主细胞，以获得包含该基因的细胞，从而获得包含该基因的细胞。该方法可用于获得编码糖基转移酶的基因。

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