Tetraacetyl D-glucosamine hydrochloride | 5432-46-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Tetraacetyl D-glucosamine hydrochloride
• 英文别名: 2-amino-2-deoxy-1,3,4,6-tetra-O-acetyl-D-glucopyranose hydrochloride；1,3,4,6-tetra-O-acetyl-3-D-glucosamine hydrochloride；1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-D-glucopyranose；acetyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-D-glucopyranoside hydrochloride；1,3,4,6-tetra-O-acetyl-β-D-glucosamine hydrochloride；1,3,4,6-tetra-O-acetylglucosamine hydrochloride；(3R,4R,5S,6R)-2,4,5-triacetoxy-6-(acetoxymethyl)-tetrahydro-2H-pyran-3-aminium chloride；[(3R,4R,5S,6R)-2,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-3-yl]azanium;chloride
• CAS: 5432-46-2
• 化学式: C₁₄H₂₁NO₉*ClH
• 分子量: 383.783
• InChiKey: BQLUYAHMYOLHBX-LEXQQUKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.55
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Tetraacetyl D-glucosamine hydrochloride 在 磷酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-deoxy-2-[(1-oxo-2-propyn-1-yl)amino]-D-glucopyranose-3,4,6-triacetate-1-(dihydrogen phosphate)
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Uridine Diphosphate-GlcNAc and Uridine Diphosphate-GalNAc Analogs for the Preparation of Unnatural Glycosaminoglycans

  摘要：

  Eight N-acetylglucosamine-1-phosphate and N-acetylgalactosamine-1-phosphate analogs have been synthesized chemically and were tested for their recognition by the GlmU uridyltransferase enzyme. Among these, only substrates that have an amide linkage to the C-2 nitrogen were transferred by GlmU to afford their corresponding uridine diphosphate(UDP)-sugar nucleotides. Resin-immobilized GlmU showed comparable activity to nonimmobilized GlmU and provides a more facile final step in the synthesis of an unnatural UDP-donor. The synthesized unnatural UDP-donors were tested for their activity as substrates for glycosyltransferases in the preparation of unnatural glycosaminoglycans in vitro. A subset of these analogs was useful as donors, increasing the synthetic repertoire for these medically important polysaccharides.

  DOI：

  10.1021/jo202322k
• 作为产物：
  描述：

  (3R,4R,5S,6R)-6-(Acetoxymethyl)-3-(benzylideneamino)tetrahydro-2H-pyran-2,4,5-triyl triacetate 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 Tetraacetyl D-glucosamine hydrochloride
  参考文献：
  名称：

  新型黄酮曼尼希碱衍生物作为潜在抗菌剂的设计，合成和生物学评估。

  摘要：

  摘要使用曼尼希反应合成了一系列含有黄酮的新的曼尼希碱衍生物。抗真菌活性的结果并不理想，但与黄酮类化合物相比，其抗真菌作用有所提高。之后，使用四种细菌对这些化合物进行了抗菌实验。与新霉素（MIC = 2，0.25 mg / L）相比，化合物5g（MIC = 0.5，0.125 mg / L）对金黄色葡萄球菌和鸡沙门氏菌显示出显着的抑制活性。化合物5s显示出对四种细菌的广谱抗菌活性（MIC = 1、0.5、2、0.05 mg / L）。所选化合物5g和5s表现出对Topo II和Topo IV的有效抑制，IC 50值为（0.25–16 mg / L）。分子对接模型表明，化合物5g和5s可通过与氨基酸残基相互作用而与靶标良好结合。它将为商业抗菌剂提供一些有价值的信息。 图形概要

  DOI：

  10.1007/s11030-018-9873-9

文献信息

• [EN] DETECTION OF MYCOBACTERIA<br/>[FR] DÉTECTION DE MYCOBACTÉRIES
  申请人：ISIS INNOVATION

  公开号：WO2011030160A1

  公开（公告）日：2011-03-17

  A method for determining the presence of mycobacteria species in an organism or biological sample, the method comprising adding to the organism or biological sample a probe molecule comprising a substrate and a label, which probe molecule can be incorporated into mycobacteria, the presence of mycobacteria being determined by a detector responsive to the presence of the label, optionally after applying a stimulus; suitable probe molecules include compounds comprising a label and a substrate, which label is can be detected by a detector responsive to the presence of the label, optionally after applying a stimulus, characterised by compound being able to engage with the active site of Antigen 85B (Ag85B) such that it can form simultaneous hydrogen bonds with two or more amino acids in the active site selected from Arg 43, Trp 264, Ser126, His 262 and Leu 42, or the corresponding amino acids in Antigen 85A (Ag85A) or Antigen 85C (Ag85C), at least one of which is with Ser126.

  一种用于确定生物体或生物样本中结核分枝杆菌种类存在的方法，该方法包括向生物体或生物样本中添加一种探针分子，该探针分子包括底物和标记，该探针分子可以被结核分枝杆菌所吸收，通过对标记的存在做出反应的探测器确定结核分枝杆菌的存在，可选地，在施加刺激后进行；适用的探针分子包括包含标记和底物的化合物，该标记可以被对标记的存在做出反应的探测器检测到，可选地，在施加刺激后进行，其特征在于该化合物能够与抗原85B（Ag85B）的活性位点结合，从而能够与所选活性位点中的两个或更多氨基酸同时形成氢键，所选活性位点包括Arg 43、Trp 264、Ser126、His 262和Leu 42，或者抗原85A（Ag85A）或抗原85C（Ag85C）中对应的氨基酸，其中至少一个与Ser126形成氢键。
• Rationally Designed Short Polyisoprenol-Linked PglB Substrates for Engineered Polypeptide and Protein N-Glycosylation
  作者：Feng Liu、Balakumar Vijayakrishnan、Amirreza Faridmoayer、Thomas A. Taylor、Thomas B. Parsons、Gonçalo J.L. Bernardes、Michael Kowarik、Benjamin G. Davis

  DOI：10.1021/ja409409h

  日期：2014.1.15

  The lipid carrier specificity of the protein N-glycosylation enzyme C. jejuni PglB was tested using a logical, synthetic array of natural and unnatural C10, C20, C30, and C40 polyisoprenol sugar pyrophosphates, including those bearing repeating cis-prenyl units. Unusual, short, synthetically accessible C20 prenols (nerylnerol 1d and geranylnerol 1e) were shown to be effective lipid carriers for PglB

  使用天然和非天然 C10、C20、C30 和 C40 聚异戊二烯醇糖焦磷酸的合乎逻辑的合成阵列测试了蛋白质 N-糖基化酶空肠弯曲菌 PglB 的脂质载体特异性，包括带有重复顺式-异戊二烯基单元的那些。不寻常的、短的、可合成的 C20 异戊烯醇（橙花醇 1d 和香叶橙花醇 1e）被证明是 PglB 糖底物的有效脂质载体。PglB 的动力学分析揭示了明确的 K(M)-仅调制与脂质链长度，从而暗示在适当浓度下成功的体外应用。这通过优化、有效的体外合成得到证实，允许 >90% 的 Asn 连接的 β-N-GlcNAc 化肽和蛋白质。这揭示了一个简单的，
• Chemical Synthesis of Modified Hyaluronic Acid Disaccharides
  作者：Marco Mende、Martin Nieger、Stefan Bräse

  DOI：10.1002/chem.201701238

  日期：2017.9.7

  report a chemical synthesis towards new modified hyaluronic acid oligomers by using only commercially available d‐glucose and d‐glucosamine hydrochloride. The various protected hyaluronic acid disaccharides were synthesized bearing new functional groups at C‐6 of the β‐d‐glucuronic acid moiety with a view to structure‐related biological activity tests. The orthogonal protecting group pattern allows ready

  本文中，我们仅使用市售的d-葡萄糖和d-葡萄糖胺盐酸盐报告了化学合成新的透明质酸低聚物的方法。合成了各种受保护的透明质酸二糖，在β- d-葡萄糖醛酸部分的C-6处带有新的官能团，以期进行结构相关的生物学活性测试。正交保护基图案允许容易地获得相应的高级低聚物。同样，对新衍生物的1 H NMR研究证明了各种官能团对分子内电子环境的影响。
• Chiral Schiff base Ligated Dioxomolybdenum (VI) Complexes and their Asymmetric Catalytic Properties in the Epoxidation of Styrene
  作者：Yan Sui、Dongsheng Liu、Ronghua Hu、Xiaobo Que

  DOI：10.3184/174751912x13457309578443

  日期：2012.10

  Two series of Schiff base dioxomolybdenum (VI) complexes of the general formula [MoO2(L)(MeOH)] (L = D-glucosamine-derived Schiff base) have been synthesised, characterised and their asymmetric catalytic activities evaluated through the epoxidation of styrene. The molybdenum complexes with acetyl-protected D-glucosamine Schiff base ligands exhibited higher enanatioselectivity than those with unprotected

  已经合成、表征了两个系列的通式为 [MoO2(L)(MeOH)]（L = D-氨基葡萄糖衍生的 Schiff 碱）的 Schiff 碱二氧钼 (VI) 配合物，并通过苯乙烯的环氧化评估了它们的不对称催化活性. 与未受保护的糖配体相比，具有乙酰基保护的 D-氨基葡萄糖席夫碱配体的钼配合物表现出更高的对映选择性。通过乙酰基保护 D-氨基葡萄糖是提高不对称催化环氧化活性的有效途径。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：UNIV OSLO

  公开号：WO2018033719A1

  公开（公告）日：2018-02-22

  The invention provides compounds for use in a method of treating and/or preventing a bacterial infection in a human or non-human mammal, said method comprising administration of said compound in combination with (either simultaneously, separately, or sequentially) a β-lactam antibiotic, wherein said compound has the general formula I: (I) (wherein: Q is a lipophilic, zinc chelating moiety which is selective for Zn2+ ions and which comprises at least one, preferably two or more (e.g 2, 3 or 4), optionally substituted, unsaturated heterocyclic rings, e.g. 5 or 6-membered heterocyclic rings (such rings preferably include at least one heteroatom selected from N, S and O, preferably N); wherein any optional substituents may be selected from C1-6 alkyl, C1-6 alkoxy, halogen, nitro, cyano, amine, and substituted amine; each L, which may be the same or different, is a covalent bond or a linker; each W, which may be the same or different, is a non-peptidic hydrophilic group which comprises one or more hydroxy groups; and x is an integer from 1 to 3) or a stereoisomer, pharmaceutically acceptable salt or prodrug thereof.

  该发明提供了一种化合物，用于治疗和/或预防人类或非人哺乳动物体内的细菌感染，所述方法包括将该化合物与β-内酰胺类抗生素（可以同时、分开或顺序地）结合给药，其中所述化合物具有一般式I：（I）（其中：Q是一个亲脂性、选择性结合Zn2+离子的基团，包括至少一个，最好是两个或更多（例如2、3或4个），可选择地取代的不饱和杂环环，例如5或6元杂环环（这些环最好包括至少一个从N、S和O中选择的杂原子，最好是N）；其中任何可选择的取代基可以选择自C1-6烷基、C1-6烷氧基、卤素、硝基、氰基、胺和取代胺；每个L，可以相同也可以不同，是一个共价键或一个连接基；每个W，可以相同也可以不同，是一个非肽性亲水基团，包括一个或多个羟基；x是1到3之间的整数）或其立体异构体、药学上可接受的盐或前药。