p-nitrophenyl 2-acetamido-4-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside | 219727-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 2-acetamido-4-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside
• 英文别名: p-nitrophenyl 2-amino-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside；p-nitrophenyl 2-acetylamino-4-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside；GlcN(b1-4)GlcNAc(b)-O-Ph(4-NO2)；N-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]acetamide
• CAS: 219727-01-2
• 化学式: C₂₀H₂₉N₃O₁₂
• 分子量: 503.463
• InChiKey: XWBZMNPPEDDGFJ-GZDRNHDFSA-N

物化性质

• 沸点：
  882.8±65.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  239
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 2-acetamido-4-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside 在 Serratia proteamaculans chitinase D D₁₅₁N/Y₁₅₄F/Y₂₂₆W mutant 作用下， 生成
  参考文献：
  名称：

  N -d-乙酰氨基葡萄糖和d-氨基葡萄糖交替的化学酶法合成壳寡糖

  摘要：

  壳寡糖（CHOS）是N-乙酰氨基葡糖（GlcNAc，A）和d-氨基葡糖（GlcN，D）的均聚物或杂聚物。具有特定长度和糖组成的明确定义的CHOS混合物甚至纯CHOS的生产引起了极大的兴趣，因为这些寡糖具有令人感兴趣的生物活性。虽然直接化学合成CHOS并不简单，但化学酶法已显示出一定的前景。我们已经使用工程化的糖苷水解酶通过转糖基化反应来催化活化的DA结构单元的低聚。构建基块是从随时可用的（GlcNAc）2中生成的-对通过使用黑曲霉（An CDA9）重组表达的脱乙酰基酶对非还原性末端糖进行脱乙酰化而生成-硝基苯酚。该方法使用先前描述的粘质沙雷氏菌（Serratia marcescens）ChiA的超转糖基化变体（Sm ChiA）和粘粒沙雷氏菌（Serratia proteamaculans）（Sp ChiD）的几丁质酶D的新生成的糖基化变体，导致产生的CHOS包含多达十个交替的D和A单位[（

  DOI：

  10.1021/acs.biochem.0c00839
• 作为产物：
  描述：

  p-nitrophenyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside 在 recombinant Aspergillus niger chitin deacetylase AnCDA₉ 、 cobalt(II) chloride 作用下， 以 水 为溶剂， 以98%的产率得到p-nitrophenyl 2-acetamido-4-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  N -d-乙酰氨基葡萄糖和d-氨基葡萄糖交替的化学酶法合成壳寡糖

  摘要：

  壳寡糖（CHOS）是N-乙酰氨基葡糖（GlcNAc，A）和d-氨基葡糖（GlcN，D）的均聚物或杂聚物。具有特定长度和糖组成的明确定义的CHOS混合物甚至纯CHOS的生产引起了极大的兴趣，因为这些寡糖具有令人感兴趣的生物活性。虽然直接化学合成CHOS并不简单，但化学酶法已显示出一定的前景。我们已经使用工程化的糖苷水解酶通过转糖基化反应来催化活化的DA结构单元的低聚。构建基块是从随时可用的（GlcNAc）2中生成的-对通过使用黑曲霉（An CDA9）重组表达的脱乙酰基酶对非还原性末端糖进行脱乙酰化而生成-硝基苯酚。该方法使用先前描述的粘质沙雷氏菌（Serratia marcescens）ChiA的超转糖基化变体（Sm ChiA）和粘粒沙雷氏菌（Serratia proteamaculans）（Sp ChiD）的几丁质酶D的新生成的糖基化变体，导致产生的CHOS包含多达十个交替的D和A单位[（

  DOI：

  10.1021/acs.biochem.0c00839

文献信息

• Selective N-deacetylation of p-nitrophenyl N,N′-diacetyl-β-chitobioside and its use to differentiate the action of two types of chitinases
  作者：Ken Tokuyasu、Hiroshi Ono、Yuki Kitagawa、Mayumi Ohnishi-Kameyama、Kiyoshi Hayashi、Yutaka Mori

  DOI：10.1016/s0008-6215(99)00002-6

  日期：1999.3

  We report the synthesis of a novel compound for chitinase assays, p-nitrophenyl 2-acetamido-4-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-beta-D-glucopyranoside [GlcNGlcNAc-pNP] by selective N-deacetylation of p-nitrophenyl 2-acetamido-4-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-beta-D-glucopyranoside [(GlcNAc)(2)-pNP] using a purified chitin deacetylase isolated from Colletotrichum lindemuthianum ATCC 56676. FABMS,H-1 NMR, and C-13 NMR analyses confirmed the structure of this new compound. This disaccharide derivative can be used to distinguish special chitinases that effectively remove partially deacetylated parts of substrates within a mixture of chitinases which degrades (GlcNAc)(2)-pNP. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Reverse hydrolysis reaction of chitin deacetylase and enzymatic synthesis of β-d-GlcNAc-(1→4)-GlcN from chitobiose
  作者：Ken Tokuyasu、Hiroshi Ono、Kiyoshi Hayashi、Yutaka Mori

  DOI：10.1016/s0008-6215(99)00213-x

  日期：1999.11

  We found that a chitin deacetylase from Colletotrichum lindemuthianum could acetylate free amino sugar residues into N-acetylated forms in the presence of 3.0 M sodium acetate. The result was analyzed using a beta-N-acetyl-hexosaminidase-coupled assay system with p-nitrophenyl beta-amino-2-deoxy-beta-D-glucopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside as the substrate, and the liberation of p-nitrophenol was observed as a consequence of enzymatic N-acetylation of the glucosamine residue at the nonreducing end of the substrate. The chitin deacetylase also acetylated chitobiose and chitotetraose as substrates, which was evidenced by the decrease in the amount of free amino sugar residues in the chitooligosaccharides. The reaction product of chitobiose after the acetylation reaction was exclusively 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1 --> 4)-2-amino-2-deoxy-D-glucose [GlcNAcGlcN], the structure of which was determined by FABMS and NMR analyses. This study offers a novel method for enzymatic N-acetylation of amino sugars, and especially with chitobiose as substrate, a selectively N-acetylated product, GlcNAcGlcN, can be synthesized. (C) 1999 Elsevier Science Ltd. All rights reserved.
• JPH10330392A
  申请人：——

  公开号：JPH10330392A

  公开（公告）日：1998-12-15
• US5994520A
  申请人：——

  公开号：US5994520A

  公开（公告）日：1999-11-30
• Chemoenzymatic Synthesis of Chito-oligosaccharides with Alternating <i>N</i>-<scp>d</scp>-Acetylglucosamine and <scp>d</scp>-Glucosamine
  作者：Rianne A. G. Harmsen、Berit Bjugan Aam、Jogi Madhuprakash、Anne Grethe Hamre、Ethan D. Goddard-Borger、Stephen G. Withers、Vincent G. H. Eijsink、Morten Sørlie

  DOI：10.1021/acs.biochem.0c00839

  日期：2020.12.8

  While direct chemical synthesis of CHOS is not straightforward, chemo-enzymatic approaches have shown some promise. We have used engineered glycoside hydrolases to catalyze oligomerization of activated DA building blocks through transglycosylation reactions. The building blocks were generated from readily available (GlcNAc)2-para-nitrophenol through deacetylation of the nonreducing end sugar with a recombinantly

  壳寡糖（CHOS）是N-乙酰氨基葡糖（GlcNAc，A）和d-氨基葡糖（GlcN，D）的均聚物或杂聚物。具有特定长度和糖组成的明确定义的CHOS混合物甚至纯CHOS的生产引起了极大的兴趣，因为这些寡糖具有令人感兴趣的生物活性。虽然直接化学合成CHOS并不简单，但化学酶法已显示出一定的前景。我们已经使用工程化的糖苷水解酶通过转糖基化反应来催化活化的DA结构单元的低聚。构建基块是从随时可用的（GlcNAc）2中生成的-对通过使用黑曲霉（An CDA9）重组表达的脱乙酰基酶对非还原性末端糖进行脱乙酰化而生成-硝基苯酚。该方法使用先前描述的粘质沙雷氏菌（Serratia marcescens）ChiA的超转糖基化变体（Sm ChiA）和粘粒沙雷氏菌（Serratia proteamaculans）（Sp ChiD）的几丁质酶D的新生成的糖基化变体，导致产生的CHOS包含多达十个交替的D和A单位[（