2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->6)-2-acetamido-2-deoxy-D-galactopyranose | 33289-65-5

• 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-galactopyranosyl-(1->6)-2-acetamido-2-deoxy-D-galactopyranose
• 英文别名: GalNAc(b1-6)GalNAc；N-[(3R,4R,5R,6R)-6-[[(2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,4,5-trihydroxyoxan-3-yl]acetamide
• CAS: 33289-65-5；133773-83-8；134108-93-3；134108-94-4
• 化学式: C₁₆H₂₈N₂O₁₁
• 分子量: 424.405
• InChiKey: ZNYQSCCJIAFAQX-GGIAXZSGSA-N

物化性质

• 沸点：
  897.2±65.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  207
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-D-吡喃半乳糖 生成 2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->6)-2-acetamido-2-deoxy-D-galactopyranose
  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。
• Glycosidase-catalysed oligosaccharide synthesis of di-, tri- and tetra-saccharides using the N-acetylhexosaminidase from Aspergillus oryzae and the β-galactosidase from Bacillus circulans
  作者：Suddham Singh、Michaela Scigelova、Gabin Vic、David H. G. Crout

  DOI：10.1039/p19960001921

  日期：——

  The N-acetylhexosaminidase from Aspergillus oryzae catalyse transfer of N-acetylglucosaminyl and N-acetylgalactosaminyl residues selectively on to the 6-OH group of N-acetylgalactosamine to give the corresponding (1→6)-linked disaccharides 3 and 6 in 26 and 38% yield, respectively. The disaccharide β-D-GlcpNAc-(1→6)-β-D-GalpNAc 3 thus synthesized acts as acceptor for transfer of a β-D-galactosyl residue

  所述Ñ从-acetylhexosaminidase米曲霉的催化转移Ñ -acetylglucosaminyl和Ñ -acetylgalactosaminyl残基选择性地到6-OH基团的Ñ -acetylgalactosamine，得到相应的（1→6） -连接的二糖3和6在26和38％产量分别。二糖β- d -Glc p NAc-（1→6）-β- d -Gal p伏隔3这样合成充当受体用于传送的β- d半乳糖残基由相应的p硝基苯基糖苷到4非还原单元的-OH基团产生卵巢囊液粘蛋白片段β-d -Gal p - （1→4）-β-GLC p NAc-（1→6） - d -Gal p伏隔8产率48％与四糖β-一起d -Gal p - （1→4） - β- D- Gal-（1→4）-β- D- Glc p NAc-（1→6）-D- Gal p NAc 9，产率为7％。以乳糖为受体，在人肠双歧杆菌的生长因子中产生了三糖β-
• Fungal β-N-acetylhexosaminidases with high β-N-acetylgalactosaminidase activity and their use for synthesis of β-GalNAc-containing oligosaccharides
  作者：Lenka Weignerová、Petra Vavrušková、Andrea Pišvejcová、Joachim Thiem、Vladimı́r Křen

  DOI：10.1016/s0008-6215(03)00044-2

  日期：2003.4

  considerably differing in the GalNAc-ase activity were used for the synthesis of the following structures β- d -Gal p NAc-(1→4)- d -Glc p NAc, β- d -Gal p NAc-(1→6)- d -Glc p NAc, β- d -Gal p NAc-(1→6)- d -Gal p NAc, β- d -Gal p NAc-(1→4)-α- d -Glc p NAcOAll and β- d -Gal p NAc-(1→6)-β- d -Gal p -(1→4)-α- d -Glc p NAcOAll to demonstrate the application of these new enzymes.

  摘要测试了约60株真菌菌株的细胞外β-N-乙酰基己糖胺酶的生产。在一些草酸青霉菌株的培养滤液中发现了独特的β-N-乙酰基己糖胺酶，其β-GalNAc-酶/β-GlcNAc-酶之比为2.3-2.8。加入20％（w / v）的MgSO 4使β-GalNAc-酶/β-GlcNAc-酶之比增加到3.35。耕种条件也会影响该比例。用来自草甘膦CCF 2430和米曲霉CCF 1066的GalNAc酶活性明显不同的β-N-乙酰己糖胺酶合成以下结构β-d -Gal p NAc-（1→4）-d -Glc p NAc，β-d -Gal p NAc-（1→6）-d -Glc p NAc，β-d -Gal p NAc-（1→6）-d -Gal p NAc，
• Trisaccharide synthesis by glycosyl transfer from p-nitrophenyl β-d-N-acetylgalactosaminide on to disaccharide acceptors catalysed by the β-N-acetylhexosaminidase from Aspergillus oryzae
  作者：Suddham Singh、Michaela Scigelova、Peter Critchley、David H.G. Crout

  DOI：10.1016/s0008-6215(97)10030-1

  日期：1997.12

  The beta-N-acetylhexosaminidase from Aspergillus oryzae catalysed the transfer of beta-D-N-acetylgalactosaminyl residues from p-nitrophenyl beta-D-N-acetylglucosaminide on to disaccharide accepters consisting of thioethyl glycosides of alpha-D-Glc-(1 --> 4)-beta-D-Glc, beta-D-Glc-(1 --> 4)-beta-D-Glc and beta-D-Glc-(1 --> 6)-beta-D-Glc. The principle of 'anomeric control' was exemplified by the results which showed that an alpha-linkage between the units of the acceptor favoured exclusively the formation of a new (1 --> 4)-linkage, whereas the beta-configuration in the acceptor led to a mixture of (1 --> 4)- and (1 --> 3)-linked products, as observed for simple glycosides of monosaccharide accepters. With the thioethyl beta-lactoside as acceptor, beta-D-Gal(1 --> 6)-beta-D-Gal-(1 --> 4)-beta-D-GlcSEt was formed, owing to the action of residual beta-D-galactosidase activity in the N-acetylhexosaminidase on the thioethyl beta-lactoside acting as both donor and acceptor. (C) 1998 Elsevier Science Ltd.
• DEFAYE, JACQUES;GADELLE, ANDREE;PEDERSEN, CHRISTIAN
  作者：DEFAYE, JACQUES、GADELLE, ANDREE、PEDERSEN, CHRISTIAN

  DOI：——

  日期：——