2-acetamido-4-O-(2-amnio-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-4-O-(2-amnio-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranoside
• 英文别名: N^I-acetylchitobiose；N-acetyl chitobiose；GlcN(b1-4)GlcNAc；N-[(3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₁₄H₂₆N₂O₁₀
• 分子量: 382.368
• InChiKey: TVLSMEPJGATPGK-UEVOBBHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  204
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-acetamido-4-O-(2-amnio-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranoside 在 Humicola insolens Cel₇B E₁₉₇A H₂₀₉A glycosynthase triflic azide 、 三乙胺 、 zinc(II) chloride 作用下， 以 甲醇 、 phosphate buffer 、 二氯甲烷 、 acetate buffer 、 水 为溶剂， 反应 16.5h， 生成 allyl O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->4)-2-azido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-β-D-glucopyranoside
  参考文献：
  名称：

  Unexpected regioselectivity of Humicola insolens Cel7B glycosynthase mutants

  摘要：

  Four Humicola insolens Ce17B glycoside hydrolase mutants have been evaluated for the coupling of lactosyl fluoride on O-allyl N-I-acetyl-2(II)-azido-beta-chitobioside. Double mutants Ce17B E197A H209A and Ce1713 E197A H209G preferentially catalyze the formation of a beta-(1 -> 4) linkage between the two disaccharides, while single mutant Cel7B E197A and triple mutant Cel7B E197A H209A A211T produce predominantly the beta-(1 -> 3)-linked tetrasaccharide. This result constitutes the first report of the modulation of the regioselectivity through site-directed mutagenesis for an endoglycosynthase. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.12.017
• 作为产物：
  描述：

  N,N'-Diacetylchitobiose 在 盐酸 、 sodium tetrahydroborate 、 chitin deacetylase 作用下， 生成 2-acetamido-4-O-(2-amnio-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranoside
  参考文献：
  名称：

  Deacetylation of chitin oligosaccharides of dp 2–4 by chitin deacetylase from Colletotrichum lindemuthianum

  摘要：

  Chitin oligosaccharides of degree of polymerization 2-4 were deacetylated by purified chitin deacetylase isolated from Colletotrichum lindemuthianum to give their corresponding breakdown products after purification by liquid chromatography. Data from FABMS analyses suggested that N, N', N '', N'''-tetraacetylchitotetraose and N, N', N ''-triacetylchitotriose were converted into fully-deacetylated corresponding chitosan oligomers. Conversely, N,N'-diacetylchitobiose [(GlcNAc)(2)] was deacetylated to give a product which showed an [M + H](+) pseudomolecular ion at m/z 383, suggesting that either of the two acetyl groups were removed. Further data from H-1 NMR analyses confirmed that the reaction product was 2-acetamido-4-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-D-glucose [GlcN-GlcNAc]. The enzymatic method has three advantageous characteristics over chemical methods: (i) it does not cause unexpected degradation of the sugar chain, (ii) it is highly reproducible, and (iii) unique compounds such as GlcN-GlcNAc may be produced. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00166-3

文献信息

• Highly Efficient Synthesis of β(1 → 4)-Oligo- and -Polysaccharides Using a Mutant Cellulase
  作者：Sébastien Fort、Viviane Boyer、Lionel Greffe、Gideon J. Davies、Olga Moroz、Lars Christiansen、Martin Schülein、Sylvain Cottaz、Hugues Driguez

  DOI：10.1021/ja9936520

  日期：2000.6.1

  This report describes an efficient chemoenzymatic synthesis of a variety of regioselectively modified β(1→4)-oligo- and -polysaccharides. This successful approach was based on: (i) the use of a “glycosynthase” which is a Glu-197-Ala nucleophile mutant of the retaining cellulase endoglucanase I (Cel7B) from Humicola insolens and (ii) the rational design of modified acceptor and donor molecules through

  本报告描述了多种区域选择性修饰的 β(1→4)-寡糖和多糖的有效化学酶法合成。这种成功的方法基于：(i) 使用“糖合酶”，它是来自 Humicola insolens 的保留纤维素酶内切葡聚糖酶 I (Cel7B) 的 Glu-197-Ala 亲核突变体和 (ii) 修饰受体的合理设计和通过仔细检查野生型酶和突变酶的 X 射线结构给出的信息来确定供体分子。该突变体能够以高产率催化未取代和被各种单糖和二糖受体修饰的 α-糖二糖基氟的区域和立体选择性糖基化，以及通过单步反转机制聚合这些供体。
• [EN] MOLECULES WITH SOLUBILITY TAG AND RELATED METHODS<br/>[FR] MOLÉCULES AYANT UNE ÉTIQUETTE DE SOLUBILITÉ ET PROCÉDÉS ASSOCIÉS
  申请人：MERCK PATENT GMBH

  公开号：WO2022058548A1

  公开（公告）日：2022-03-24

  The present disclosure relates to molecules with a solubility tag, wherein the solubility tag comprises a chito-oligosaccharide, and to methods for increasing the solubility of a molecule. Moreover, the present disclosure relates to antibody-drug conjugates with solubility tag, methods and compounds for preparing such antibody-drug conjugates, methods for increasing the solubility of antibody-drug conjugates, antibody-drug conjugates prepared by such methods, as well as the use of such antibody-drug conjugates in medical treatment.

  本公开涉及带有溶解度标记的分子，其中溶解度标记包括壳寡糖，并且涉及增加分子溶解度的方法。此外，本公开涉及带有溶解度标记的抗体药物结合物，用于制备该抗体药物结合物的方法和化合物，增加抗体药物结合物溶解度的方法，通过这些方法制备的抗体药物结合物，以及在医疗治疗中使用这种抗体药物结合物。
• 10.1002/cjoc.202400345
  作者：Li, Jianghua、Zhang, Yan、Hu, Zhifei、Ye, Jinfeng、Cao, Hongzhi

  DOI：10.1002/cjoc.202400345

  日期：——

  great promise as a novel class insecticide and fungicide, the limited accessibility of TMG-chitotriomycin prevents its further biological evaluation. We report herein a simple and eco-friendly chemoenzymatic approach for the efficient synthesis of TMG-chitotriomycin and its analogues. In this strategy, the readily available chitosan was enzymatically hydrolyzed and chemically N-acetylated to afford

  N , N , N -三甲基-D-葡萄糖胺 (TMG)-chitotriomycin 是一种天然存在的几丁质相关寡糖，是昆虫和真菌的特异性 β- N - 乙酰己糖胺酶 (HexNAcases) 抑制剂。尽管TMG-壳三霉素作为新型杀虫剂和杀菌剂具有广阔的前景，但TMG-壳三霉素的可及性有限阻碍了其进一步的生物学评价。我们在此报告了一种简单且环保的化学酶方法，用于有效合成 TMG-壳三霉素及其类似物。在该策略中，对容易获得的壳聚糖进行酶水解和化学N-乙酰化，以提供从二糖到六糖的壳寡糖。这些壳寡糖被两种不同的几丁质脱乙酰酶选择性脱乙酰基，然后进行化学N-三甲基化，以获得所需的TMG-壳三霉素和总共13种TMG-壳三霉素类似物，在4个步骤的最长线性序列中，总产率超过12%。
• Deacetylation of chitin oligosaccharides of dp 2–4 by chitin deacetylase from Colletotrichum lindemuthianum
  作者：Ken Tokuyasu、Hiroshi Ono、Mayumi Ohnishi-Kameyama、Kiyoshi Hayashi、Yutaka Mori

  DOI：10.1016/s0008-6215(97)00166-3

  日期：1997.9

  Chitin oligosaccharides of degree of polymerization 2-4 were deacetylated by purified chitin deacetylase isolated from Colletotrichum lindemuthianum to give their corresponding breakdown products after purification by liquid chromatography. Data from FABMS analyses suggested that N, N', N '', N'''-tetraacetylchitotetraose and N, N', N ''-triacetylchitotriose were converted into fully-deacetylated corresponding chitosan oligomers. Conversely, N,N'-diacetylchitobiose [(GlcNAc)(2)] was deacetylated to give a product which showed an [M + H](+) pseudomolecular ion at m/z 383, suggesting that either of the two acetyl groups were removed. Further data from H-1 NMR analyses confirmed that the reaction product was 2-acetamido-4-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-D-glucose [GlcN-GlcNAc]. The enzymatic method has three advantageous characteristics over chemical methods: (i) it does not cause unexpected degradation of the sugar chain, (ii) it is highly reproducible, and (iii) unique compounds such as GlcN-GlcNAc may be produced. (C) 1997 Elsevier Science Ltd.
• 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.