β-1-N-benzamido-D-glucopyranose | 15354-97-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-1-N-benzamido-D-glucopyranose
• 英文别名: N-(β-D-glucopyranosyl)benzamide；N-β-D-glucopyranosylbenzamide；N-Benzoyl-β-D-glucopyranosylamin；N-(phenylcarbonyl)-beta-D-glucopyranosylamine；N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]benzamide
• CAS: 15354-97-9
• 化学式: C₁₃H₁₇NO₆
• 分子量: 283.281
• InChiKey: SPYSOSUFGSNSMY-BZNQNGANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 27.5h， 生成 β-1-N-benzamido-D-glucopyranose
  参考文献：
  名称：

  碳水化合物基支架的开发，用于限制识别基团的表达。二价配体的扩展及其对二聚受体结构的影响。

  摘要：

  已经通过NMR研究了糖基酰胺的溶液结构。与以Z-抗结构为主的仲芳族糖基酰胺相反，叔芳族糖基酰胺显示出对E-抗结构的强烈偏好。这些种类的分子表现出的结构多样性似乎很重要，因为芳香环或与芳香环相连的基团的方向性可以通过选择在异头中心处具有仲酰胺或叔酰胺来确定，并且可以在设计具有碳水化合物支架的生物活性分子时应予以考虑。还对相关的二价仲和叔糖基酰胺进行了结构分析，这些化合物显示出与单价化合物相似的偏好。受约束的二价化合物具有促进将形成具有受限结构的簇的潜力，因此对于多价配体的作用机理的新颖研究具有潜力。此类化合物的可能应用将用作支架的设计和合成，以促进蛋白质-蛋白质或其他受体-受体相互作用。设计成与识别碳水化合物的蛋白结合的限制性二价（或更高阶）配体的亲和力，其亲和力可能明显高于没有这些特性的单价对应物或多价配体，而后者会促进成簇并同时促进蛋白质-蛋白质相互作用。这可能是开发基于碳水化合物的疗法的一种新方法。

  DOI：

  10.1021/jo034336d

文献信息

• The Reaction of Thio Acids with Azides:  A New Mechanism and New Synthetic Applications
  作者：Ning Shangguan、Sreenivas Katukojvala、Rachel Greenberg、Lawrence J. Williams

  DOI：10.1021/ja0294919

  日期：2003.7.1

  A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides

  提出了一种基于硫代酸和有机叠氮化物反应的基本机理修正的新酰胺合成策略。数据表明在该反应中没有形成胺作为中间体。建议了通过噻三唑啉中间体进行的替代机制。该反应已用于制备使用常规方法难以获得的简单且结构复杂的酰胺。该反应具有化学选择性，对未受保护的底物有效，并与非质子和质子溶剂（包括水）相容。
• Synthesis of Glycosyl Amides Using Selenocarboxylates as Traceless Reagents for Amide Bond Formation
  作者：Luana Silva、Ricardo F. Affeldt、Diogo S. Lüdtke

  DOI：10.1021/acs.joc.6b00832

  日期：2016.7.1

  were successfully prepared in good yields from a broad range of substrates, including furanosyl and pyranosyl derivatives. The methodology successfully relied on the in situ generation of lithium selenocarboxylates from Se/LiEt3BH and acyl chlorides or carboxylic acids and their reaction with sugar azides. A key aspect of the present protocol is that we start from elemental selenium; isolation and handling

  从包括呋喃糖基和吡喃糖基衍生物在内的多种底物成功成功地制备了碳水化合物衍生的酰胺。该方法学成功地依赖于从Se / LiEt 3 BH和酰基氯或羧酸中原位生成硒酸锂锂，以及它们与糖叠氮化物的反应。本协议的一个关键方面是我们从元素硒开始。避免了所有反应性和敏感的含硒中间体的分离和处理，因此提供了硒代羧酸盐无痕试剂的状态。
• β-Galactosidase catalysed transglycosylation in aqueous organic media using glycosylasparagine mimics as novel acceptors
  作者：Kuttikode Priya、Duraikkannu Loganathan

  DOI：10.1016/s0040-4020(98)01090-4

  日期：1999.1

  transglycosylation catalysed by β-galactosidase from Bacillus circulans. Acceptor ability of 2 was shown to be as good as or better than several O-glycosides employed earlier. Systematic variation of reaction conditions led to improvement of yield from 5 % to 41 %. Interestingly, use of aqueous organic media has led to increased yield of transglycosylation and the 1,3-linked disaccharide was formed in considerable

  研究了β-1-N-乙酰氨基-D-吡喃葡萄糖（2）（一种N-糖蛋白连接区的模型）及其苯甲酰胺类似物作为环芽孢杆菌β-半乳糖苷酶催化的糖基转移反应的新型受体。已显示2的受体能力与较早采用的几种O-糖苷一样好或更好。反应条件的系统变化导致产率从5％提高到41％。有趣的是，水性有机介质的使用导致转糖基化的产率增加，并且在所有检查的条件下均形成大量的1，3-连接的二糖。
• Synthesis of a glucuronic acid and glucose conjugate library and evaluation of effects on endothelial cell growth
  作者：Nigel Pitt、Rhona M. Duane、Alan O' Brien、Helena Bradley、Stephen J. Wilson、Kathy M. O' Boyle、Paul V. Murphy

  DOI：10.1016/j.carres.2004.05.024

  日期：2004.8

  Compounds that alter endothelial cell growth are of interest in the development of angiogenesis modulators. A structurally diverse series of saccharide derivatives (glycosylamide conjugates) have been synthesized and evaluated for their effects on bovine aortic endothelial cell (BAEC) growth. Heparin-albumin (HA) reduced BAEC growth by 32% at 10 mug/mL and a number of the novel saccharide conjugates from the library were found to mimic the effect of HA as they also inhibit endothelial cell survival under identical conditions. Two thiophene conjugates, thioglucamide (24% inhibition at 35 muM) and a related glucuronide (26% inhibition at 33 muM) were the most potent inhibitors of BAEC growth, as determined using a methylthiazol tetrazoliurn (MTT) assay. The effects of thioglucamide and HA on absolute cell number were also studied using cell counting experiments; thioglucamide (47% after 24 h) was more potent than indicated by the MTT assay and initially reduced the BAEC number to a greater extent than HA (30% after 24 h); however, its actions were over more rapidly than were HA's as cell growth had returned to levels of the control after 72 h where HA still caused 25% inhibition. The binding of the monosaccharide conjugates to fibroblast growth factor (FGF-2) in competition with heparin-alburnin by ELISA was investigated to establish the possible mechanism by which glycoconjugates could alter growth but there was no general correlation between reduction in viable cell population and binding to FGF-2. No glycoconjugate reduced the proliferation of mouse mammary epithelial cells, nor did any alter gross cell morphology, supporting a proposal that the reduction in BAEC survival by monosaccharide conjugates such as thioglucamide is a result of the inhibition of cell proliferation rather than being an induction of cytotoxicity. These studies indicate that cell biological studies to determine the mechanism of action of the simple monosaccharide conjugates may be worthwhile. (C) 2004 Elsevier Ltd. All rights reserved.
• Amide-1,2,3-triazole bioisosterism: the glycogen phosphorylase case
  作者：Evangelia D. Chrysina、Éva Bokor、Kyra-Melinda Alexacou、Maria-Despoina Charavgi、George N. Oikonomakos、Spyros E. Zographos、Demetres D. Leonidas、Nikos G. Oikonomakos、László Somsák

  DOI：10.1016/j.tetasy.2009.03.021

  日期：2009.5

  Per-O-acetylated beta-D-glucopyranosyl azide was transformed into an intermediate iminophosphorane by PMe3 which was then acylated to N-acyl-beta-D-glucopyranosylamines. The same azide and substituted acetylenes gave 1-(beta-D-glucopyranosyl)-4-substituted-1,2,3-triazoles in Cu(I)-catalyzed azide-alkyne cycloadditions. Deprotection of these products by the Zemplen method furnished beta-D-Glc(p)-NHCO-R derivatives as well as 1-(beta-D-Glc(p))-4-R-1,2,3-triazoles which were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. Pairs of amides versus triazoles with the same R group displayed similar inhibition constants. X-ray crystallographic studies on the enzyme-inhibitor complexes revealed high similarities in the binding of pairs with R = 2-naphthyl and hydroxymethyl, while for the R = Ph and 1-naphthyl compounds a different orientation of the aromatic part and changes in the conformation of the 280s loop were observed. By this study new examples of amide-1,2,3-triazole bioisosteric relationship have been provided. (C) 2009 Elsevier Ltd. All rights reserved.