6-[(N-Benzyloxycarbonyl)amino]hexyl 2-N-acetamido-2-deoxy-β-D-glucopyranoside | 62205-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-[(N-Benzyloxycarbonyl)amino]hexyl 2-N-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: 6-(benzyloxycarbonylamino)-1-hexyl 2-acetamido-2-deoxy-β-D-glucopyranoside；benzyl N-[6-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexyl]carbamate
• CAS: 62205-57-6
• 化学式: C₂₂H₃₄N₂O₈
• 分子量: 454.521
• InChiKey: VAHQPRXFXFSDQJ-PFAUGDHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  147
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-[(N-Benzyloxycarbonyl)amino]hexyl 2-N-acetamido-2-deoxy-β-D-glucopyranoside 在 Pearlman catalyst 、 环己烯 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 6-aminohexyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  尿苷的2-脱氧-己吡喃糖基衍生物的合成作为糖基转移酶的供体底物类似物

  摘要：

  已经合成了一系列尿苷的2-脱氧-己吡喃糖基衍生物，作为UDP-糖的类似物。这些化合物在荧光测定法中作为牛β-1,4-半乳糖基转移酶I的抑制剂进行了测试，未显示出明显的抑制作用。

  DOI：

  10.1016/j.bioorg.2009.08.001
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 sodium methylate 、 氰化汞 作用下， 以 甲醇 、 硝基甲烷 、 苯 为溶剂， 反应 96.0h， 生成 6-[(N-Benzyloxycarbonyl)amino]hexyl 2-N-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  6-氨基-1-己基2-乙酰氨基-2-脱氧-3-，-4-和-6-O-β-D-吡喃半乳糖基-β-D-吡喃葡萄糖苷的合成

  摘要：

  摘要制备了具有β-（1→3）-，β-（1→4）-和β-（1→6）-构图的β-D-Gal→β-D-GlcNAc二糖的6-氨基己基糖苷。用2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-α-D-吡喃葡萄糖基氯将6-（苯甲氧基羰基氨基）-1-己醇糖基化，得到（80％）结晶β-糖苷乙酸（3），3的脱乙酰基，然后异丙基化（2，2-二甲氧基丙烷-TsOH），以总收率84％得到结晶的4，6-O-异亚丙基衍生物（5）。5 [苄基溴-BaO-Ba（OH 2）在N，N-二甲基甲酰胺中的苯甲酰化]生成其3-O-苄基衍生物，将其转化为6-（苄氧基羰基氨基）-1-己基2-乙酰氨基-3- O-苄基-2-脱氧-β-D-吡喃葡萄糖苷（7），总产率为69％。7、2、3、4的糖基化，6-四-O-乙酰基-α-D-吡喃半乳糖基溴化物（12）和三氟甲磺酸银在干燥的CH 2 Cl 2中在0°产生β-（1→6）-二糖苷（17），产

  DOI：

  10.1016/s0008-6215(00)85520-2

文献信息

• Chemo-enzymatic synthesis of glycopolymers and sequential glycopeptides bearing lactosamine and sialyl Lewisx unit pendant chains
  作者：Florence Sallas、Shin-Ichiro Nishimura

  DOI：10.1039/b001612h

  日期：——

  A variety of glycoconjugates bearing either N-acetyllactosamine or sialyl Lewisx units have been synthesised in a chemo-enzymatic way. This includes the synthesis of glycopolymer copolymerised with acrylamide and whose glucosamine unit was substituted with different kinds of side-chain. Glycopeptides with different spacer-arm glucosamine units have also been prepared and polymerised. The sugar chain

  已经以化学酶促的方式合成了各种带有N-乙酰基乳糖胺或唾液酸化的Lewis x单元的糖缀合物。这包括与丙烯酰胺共聚的糖聚合物的合成，其糖胺单元被不同种类的侧链取代。还已经制备并聚合了具有不同间隔臂葡糖胺单元的糖肽。然后使用糖基转移酶拉长糖链，以提供新的连续糖肽。在这些情况下，聚合糖簇效应导致高效的酶促糖基化。然而，根据用于每种底物的反应条件，已经注意到一些差异。
• ω-Aminoalkyl β-glycosides of N-acetylmuramyl-l-alanyl-d-isoglutamine, and their conjugates with meningococcal group C polysaccharide
  作者：Mitree M. Ponpipom、Kathleen M. Rupprecht

  DOI：10.1016/0008-6215(83)88218-4

  日期：1983.2

  The 6-aminohexyl beta-glycoside of N-acetylmuramyl-L-alanyl-D-isoglutamine and its spacer-arm-linked analog (3.8 nm) were synthesized from 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)-[2,1-d]-2- oxazoline, and coupled with meningococcal group C polysaccharide in attempts to enhance the immunogenicity of the polysaccharide antigen.

  由2-甲基-（3,4,6-三-O-乙酰基）合成N-乙酰基muramyl-L-丙氨酰-D-异谷氨酰胺的6-氨基己基β-糖苷及其间隔臂连接的类似物（3.8 nm） -1,2-二脱氧-α-D-吡喃葡萄糖基）-[2,1-d] -2-恶唑啉，并与脑膜炎球菌C组多糖偶联，试图增强多糖抗原的免疫原性。
• A New Assay For Sialyltransferases Using Fluorescein-Labelled Acceptors
  作者：Gerrit Limberg、George C. Slim、Richard H. Furneaux、Catharine A. Compston、Peter Stangier、Monica M. Palcic

  DOI：10.1002/jlac.199619961111

  日期：1996.11

  disaccharides βGal-(14)-βGlc-OR (4), βGal-(14)-βGlcNAc-OR (17), and βGal-(13)-βGlcNAc-OR (22) where OR consists of a six carbon spacer with fluorescein attached, were synthesised. Synthetic standard products were produced chemo-enzymatically on a preparative scale to yield fluorescein-labelled trisaccharides. The use of reverse phase HPLC with an ionpairing agent allowed the separation of starting materials

  描述了基于荧光素标记的受体寡糖的用于唾液酸转移酶活性的新型HPLC测定系统。荧光素标记的二糖βGal-（14）-βGlcNAc-OR（4），βGal-（14）-βGlcNAc-OR（17）和βGal-（13）-βGlcNAc-OR（22），其中OR包含六个合成了附着有荧光素的碳间隔基。以制备规模化学酶法生产合成标准产物，以产生荧光素标记的三糖。通过使用反相HPLC和离子对试剂，可以从产物中分离出原料，并分离出两种同分异构的三糖αNeu5Ac-（23/6）-βGal-（14）-βGlcNAc-OR（24和25），因此该测定法可用于测量混合物中不同的甲硅烷基转移酶活性。该测定法成功地用于检测市售酶和牛初乳的粗制品的唾液酸转移酶活性。牛初乳中主要的唾液酸转移酶活性将唾液酸α（2–6）添加到17中。
• Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine
  作者：Gerhard Kretzschmar、Wilhelm Stahl

  DOI：10.1016/s0040-4020(98)00294-4

  日期：1998.6

  The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis and antibody-binding studies of a series of parasite fuco-oligosaccharides
  作者：Anne-Marie M. van Roon、Begoña Aguilera、Francisco Cuenca、Alexandra van Remoortere、Gijsbert A. van der Marel、André M. Deelder、Herman S. Overkleeft、Cornelis H. Hokke

  DOI：10.1016/j.bmc.2005.02.009

  日期：2005.5

  Complex multifucosylated oligosaccharides are structural elements of glycoprotein and glycolipid subsets of larval, egg, and adult stages of Schistosoma, the parasitic worms that cause schistosomiasis, a serious disease affecting more than 200 million people in the tropics. The fucosylated structures are thought to play an important role in the immunology of schistosomiasis. Defined schistosomal oligosaccharides that enable immunological studies are difficult to obtain from natural sources. Therefore, we have chemically synthesized spacer-linked GlcNAc, Fuc alpha 1-2Fuc alpha 1-3GlcNAc, Fuc alpha 1-2Fuc alpha 1-3GlcNAc, and Fuc alpha 1-2Fuc alpha 1-2Fuc alpha 1-3GlcNAc. This series of linear oligosaccharides was used to screen a library of anti-schistosome monoclonal antibodies by surface plasmon resonance spectroscopy. Interestingly, the reactive antibodies could be grouped according to their specificity for the different oligosaccharides tested, showing that these oligosaccharides form different immunological entities based on the number and linkage of the fucose residues. Subsequently, the thus defined monoclonal antibodies were used to visualize the expression of the corresponding oligosaccharide epitopes by adult Schistosoma mansoni worms. (c) 2005 Elsevier Ltd. All rights reserved.