2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-D-glucopyranose
• 英文别名: GlcNAc(b1-6)GlcNAc(b1-6)GlcNAc；N-[(3R,4R,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3-acetamido-6-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxymethyl]-2,4,5-trihydroxyoxan-3-yl]acetamide
• 化学式: C₂₄H₄₁N₃O₁₆
• 分子量: 627.6
• InChiKey: MHWFKFPLUFYNOQ-IEKOOOPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  295
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  1,2-bis(N-methyl-O-propyl-hydroxylamine)disulfide 、 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-D-glucopyranose 在 三乙胺 、 Cleland's reagent 作用下， 以 N,N-二甲基甲酰胺 、 水 、 溶剂黄146 为溶剂， 反应 0.5h， 以54%的产率得到N-methyl-O-(propyl-3-thiol)-N-[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl] hydroxylamine
  参考文献：
  名称：

  Efficient synthesis and protein conjugation of β-(1→6)-d-N-acetylglucosamine oligosaccharides from the polysaccharide intercellular adhesin

  摘要：

  A wide variety of medically important biofilm forming bacteria produce similar polysaccharide intracellular adhesins (PIAs). The PIA structures consist of partially de-N-acetylated beta-(1 -> 6)-N-acetylglucosamine polymers. These exopolysaccharides are key components of the bacterial biofilm matrix. Here, we describe the efficient synthesis of PIA oligosaccharides using an acid reversion reaction of N-acetylglucosamine in HF pyridine. The PIA oligosaccharides produced by this reaction can be purified to homogeneity by size exclusion chromatography. Chemistry was developed to conjugate the PIA oligosaccharides to bovine serum albumin using a new heterobifunctional linker containing a thiol and an N-methylhydroxylamine functional group. These glycoconjugates may serve as useful precursors for the development of defined conjugate vaccines against PIA producing bacterial strains. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.021
• 作为产物：
  描述：

  D-GlcNAc 生成 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  DEFAYE, JACQUES;GADELLE, ANDREE;PEDERSEN, CHRISTIAN, CARBOHYDR. RES., 186,(1989) N, C. 177-188

  摘要：

  DOI：

文献信息

• Hydrogen fluoride-catalyzed formation of glycosides. Preparation of methyl 2-acetamido-2-deoxy-β-d-gluco- and -β-d-galacto-pyranosides, and of β-(1→6)-linked 2-acetamido-2-deoxy-d-gluco- and -d-galacto-pyranosyl oligosaccharides
  作者：Jacques Defaye、Andrée Gadelle、Christian Pedersen

  DOI：10.1016/0008-6215(89)84033-9

  日期：1989.3

  Dissolution of 2-acetamido-2-deoxy-d-glucose (1) or -d-galactose (2) in anhydrous hydrogen fluoride, followed by addition of methanol, gave stereospecifically the corresponding methyl β-d-glycopyranosides 7 and 8. When solutions of 1 or 2 in hydrogen fluoride were slowly evaporated, mixtures of exclusively β-d-(1→6)-linked di- to hexa-saccharides containing 2-acetamido-2-deoxy-glucosyl (9) and -galactosyl

  将2-乙酰氨基-2-脱氧-d-葡萄糖（1）或-d-半乳糖（2）溶解在无水氟化氢中，然后加入甲醇，立体定向地得到相应的甲基β-d-吡喃葡萄糖苷7和8。缓慢蒸发1或2在氟化氢中的溶液，仅包含2-乙酰胺基2-脱氧葡萄糖基（9）和-半乳糖基（10）的β-d-（1→6）连接的二糖至六糖的混合物）残留物；用凝胶渗透色谱法分离得到纯产物。当在适当条件下处理几丁质溶液时，也获得了化合物7和9。
• DEFAYE, JACQUES;GADELLE, ANDREE;PEDERSEN, CHRISTIAN, CARBOHYDR. RES., 186,(1989) N, C. 177-188
  作者：DEFAYE, JACQUES、GADELLE, ANDREE、PEDERSEN, CHRISTIAN

  DOI：——

  日期：——
• DEFAYE, J.;GADELLE, A.;PEDERSEN, C., CHITIN AND CHITOSAN: SOURCES, CHEM., BIOCHEM., PHYS. PROP. AND APPL.: PRO+
  作者：DEFAYE, J.、GADELLE, A.、PEDERSEN, C.

  DOI：——

  日期：——
• DEFAYE, JACQUES;GADELLE, ANDREE;PEDERSEN, CHRISTIAN
  作者：DEFAYE, JACQUES、GADELLE, ANDREE、PEDERSEN, CHRISTIAN

  DOI：——

  日期：——
• Efficient synthesis and protein conjugation of β-(1→6)-d-N-acetylglucosamine oligosaccharides from the polysaccharide intercellular adhesin
  作者：Carmen Leung、Anthony Chibba、Rodolfo F. Gómez-Biagi、Mark Nitz

  DOI：10.1016/j.carres.2008.12.021

  日期：2009.3

  A wide variety of medically important biofilm forming bacteria produce similar polysaccharide intracellular adhesins (PIAs). The PIA structures consist of partially de-N-acetylated beta-(1 -> 6)-N-acetylglucosamine polymers. These exopolysaccharides are key components of the bacterial biofilm matrix. Here, we describe the efficient synthesis of PIA oligosaccharides using an acid reversion reaction of N-acetylglucosamine in HF pyridine. The PIA oligosaccharides produced by this reaction can be purified to homogeneity by size exclusion chromatography. Chemistry was developed to conjugate the PIA oligosaccharides to bovine serum albumin using a new heterobifunctional linker containing a thiol and an N-methylhydroxylamine functional group. These glycoconjugates may serve as useful precursors for the development of defined conjugate vaccines against PIA producing bacterial strains. (C) 2009 Elsevier Ltd. All rights reserved.