2-AZIDO-2-DEOXY-1,3,4,6-?TETRAACETATED-?MANNOPYRANOSE{规格,价格需询问客服} | 139066-49-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-AZIDO-2-DEOXY-1,3,4,6-?TETRAACETATED-?MANNOPYRANOSE{规格,价格需询问客服}
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α/β-D-mannopyranose
• 英文别名: 2-deoxy-2-azido-1,3,4,6-tetra-O-acetyl-D-mannopyranoside；1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-mannopyranose；2-azido-3,4,6-tri-O-acetyl-2-deoxy-D-mannopyranose；per-O-acetyl-2-azido-2-deoxy-mannosyl acetate；2-azido-1,3,4,6-tetra-O-acetyl-D-glucose；[(2R,3S,4R,5S)-3,4,6-triacetyloxy-5-azidooxan-2-yl]methyl acetate
• CAS: 139066-49-2
• 化学式: C₁₄H₁₉N₃O₉
• 分子量: 373.32
• InChiKey: QKGHBQJLEHAMKJ-DYPLGBCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-AZIDO-2-DEOXY-1,3,4,6-?TETRAACETATED-?MANNOPYRANOSE{规格,价格需询问客服} 在 copper(ll) sulfate pentahydrate 、 三氟化硼乙醚 、 sodium ascorbate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成
  参考文献：
  名称：

  WO2023/209586

  摘要：

  公开号：
• 作为产物：
  描述：

  D-mannosamine hydrochloride 在 吡啶 、 4-二甲氨基吡啶 、 triflic azide 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 22.0h， 生成 2-AZIDO-2-DEOXY-1,3,4,6-?TETRAACETATED-?MANNOPYRANOSE{规格,价格需询问客服}
  参考文献：
  名称：

  通过重氮转移方便地合成2-叠氮基-2-脱氧醛糖†

  摘要：

  重氮从三氟甲磺酰基叠氮化物（TfN 3）转移至2-氨基-2-脱氧葡萄糖构成了制备部分保护或未保护的2-叠氮基2-脱氧醛糖的高产率，简单方法。因此，d-allosamine衍生物2得到的93％3，而重氮基转移到d葡糖胺，d甘露糖胺，和d半乳糖胺，随后通过乙酰化，得到叠氮化物5，7，和9中的74-91的产率，分别为65％和70％。

  DOI：

  10.1002/hlca.19910740842
• 作为试剂：
  描述：

  D-mannosamine hydrochloride 在 吡啶 、 4-二甲氨基吡啶 、 copper(ll) sulfate pentahydrate 、 三氟化硼乙醚 、 2-AZIDO-2-DEOXY-1,3,4,6-?TETRAACETATED-?MANNOPYRANOSE{规格,价格需询问客服} 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 phenyl 2-azido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Cytotoxic properties of d-gluco-, d-galacto- and d-manno-configured 2-amino-2-deoxy-glycerolipids against epithelial cancer cell lines and BT-474 breast cancer stem cells

  摘要：

  Glycosylated antitumor ether lipids (GAELs) 6 and 7 containing a alpha- or beta-D-gluco-configured 2-amino-2-deoxy (2-NH2-Glc) sugar moiety linked to a glycerolipid aglycone kill cancer cell lines via a non-apoptotic mechanism that could be exploited to kill cancer stem cells. To test this hypothesis and develop novel potent GAEL analogs, we synthesized GAELS which contain D-galacto- and D-manno-configured 2-amino-2-deoxy sugar moieties (2-NH2-Gal or 2-NH2-Man) and investigated their cytotoxicity against human epithelial cancer cell lines and cancer stem cells derived from BT-474 breast cancer cells. Within the class of D-galacto-configured GAELs, we prepared both O- and S-glycosidic linkages as well as their corresponding alpha- and beta-anomers and screened against breast (BT-474, JIMT-1 and BT-549), pancreas (MiaPaCa2) and prostate cancer (DU145, PC3) cancer cell lines. The alpha-anomeric 2-NH2-Gal-based lipid 1 was the most active of all the compounds tested with CC50 values of 4.4-8 mu M and is the most active GAEL synthesized to date. The beta-anomer 2 was 4->5-fold less active than 1. Replacement of the alpha-O-glycosidic by an alpha-S-glycosidic linkage resulted in a 2-4-fold reduction in activity, while the beta-S-glycolipid 4 was inactive. In comparison, alpha-configured 2-NH2-Man-based glycerolipid 5 displayed very little activity with CC50 > 30 mu M. The effect of the most active GAELs, 1, 6, or 7, on cancer stem cell viability revealed that all three inhibited the formation of tumorspheres from BT-474 cancer stem cell lines, caused the disintegration of preformed tumorspheres and resulted in total loss of cell viability of the cancer stem cells at concentrations of 20 mu M. In contrast, the related antitumor ether lipid gold standard, edelfosine that is in clinical development was much less effective in preventing tumorsphere formation and affecting the viability of the cancer stem cells. Taken together our study demonstrates that alpha-GAEL anomers are more potent than their corresponding beta-anomers and that the nature of the CHO moiety as well as the glycosidic bond significantly affects activity. The study also showed that GAELs are effective in killing CSCs while the apoptosis-inducing edelfosine is not. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.057

文献信息

• Synthesis of novel triazole-derived glycopeptides as analogs of α-dystroglycan mucins
  作者：Marcelo Fiori Marchiori、Giulia Pompolo Iossi、Leandro Oliveira Bortot、Marcelo Dias-Baruffi、Vanessa Leiria Campo

  DOI：10.1016/j.carres.2018.11.004

  日期：2019.1

  followed by hydrogenation reactions. Subsequently, glycopeptides 3 (23%) and 4 (12%) were obtained by solid phase synthesis, involving sequential couplings of Fmoc-protected amino acids or the glycosyl amino acids 1 and 2, followed by cleavage from resin, N-acetylation and O-deacetylation (NaOMe) reactions. Lastly, enzymatic galactosylation of glycopeptide 3 with bovine β-1,4-GalT showed that it was not

  α-Dystroglycan（α-DG）粘蛋白对于维持肌纤维的结构和功能稳定性至关重要，并且在糖基化程度低时，它们直接参与病理过程，例如营养不良性糖病。因此，这项工作报告了新的1,2,3-三唑衍生的糖基氨基酸αGlcNAc-1-O-三唑-2Manα-ThrOH（1）和Gal-β1,4-αGlcNAc-1-O-三唑的合成-2Manα-ThrOH（2），然后固相组装得到相应的糖肽NHAcThrVal [αGlcNAc-1-triazol-2Manα] ThrIleArgGlyOH（3）和NHAcThrVal [Gal-β1,4-αGlcNAc-1-triazol-2Manα] ThrIleArgGlyOH（4）作为α-DG粘蛋白的类似物。铜（I）辅助合成1（72％）和2（35％）的糖基氨基酸1，叠氮化物-糖基氨基酸αManN3-FmocThrOBn（5）与相应的炔烃官能化糖2'-丙炔基-αGl
• 具有抗肿瘤活性的砷糖化合物及其制法和应 用
  申请人：湖北工程学院

  公开号：CN105175470B

  公开（公告）日：2018-01-05

  具有抗肿瘤活性的砷糖化合物及其制法和应用。本发明涉及N‑（4”‑(1”,3”,2”‑二硫砷烷)苯基）‑1‑（1’,3’,4’,6’‑O‑乙酰基‑D‑葡萄糖）‑1，2，3‑三唑‑4‑甲酰胺。由阿散酸经过二氧化硫还原，盐酸成盐，碱化，上保护基制备4‑(1,3,2‑二硫砷烷)苯胺，然后与炔丙酸在N,N’‑环己基碳二亚胺作用下生成N‑(4‑(1,3,2‑二硫砷烷)苯基)炔酰胺；2‑叠氮‑1,3,4,6‑O‑乙酰基‑D‑葡萄糖与N‑(4‑(1,3,2‑二硫砷烷)苯基)炔酰胺反应生成N‑（4”‑氧化砷苯基）‑1‑（1’,3’,4’,6’‑O‑乙酰基‑D‑葡萄糖）‑1，2，3‑三唑‑4‑甲酰胺；所得产物再与1，2‑乙二硫醇反应得到本发明所述化合物。
• A safe and convenient method for the preparation of triflyl azide, and its use in diazo transfer reactions to primary amines
  作者：Alexander Titz、Zorana Radic、Oliver Schwardt、Beat Ernst

  DOI：10.1016/j.tetlet.2006.01.157

  日期：2006.4

  A safe and convenient method for the copper(II)-catalyzed diazo transfer from triflyl azide to primary amines is reported. By replacing CH2Cl2 by toluene the formation of hazardous side products, for example, azido-chloromethane and diazidomethane can be avoided.

  报道了一种安全方便的铜（II）催化重氮从三氟叠氮化物转移到伯胺的方法。通过用甲苯代替CH 2 Cl 2，可以避免形成危险的副产物，例如叠氮基氯甲烷和重氮基甲烷。
• Enhancing Potency and Selectivity of a DC‐SIGN Glycomimetic Ligand by Fragment‐Based Design: Structural Basis
  作者：Laura Medve、Silvia Achilli、Joan Guzman‐Caldentey、Michel Thépaut、Luca Senaldi、Aline Le Roy、Sara Sattin、Christine Ebel、Corinne Vivès、Sonsoles Martin‐Santamaria、Anna Bernardi、Franck Fieschi

  DOI：10.1002/chem.201903391

  日期：2019.11.18

  pseudo-dimannoside ligands guided by fragment-based design allowed for the exploitation of an ammonium-binding region in the vicinity of the mannose-binding site of DC-SIGN, leading to the synthesis of a glycomimetic antagonist (compound 16) of unprecedented affinity and selectivity against the related lectin langerin. Here, the computational design of pseudo-dimannoside derivatives as DC-SIGN ligands, their synthesis

  通过基于片段的设计指导对假二金刚烷糖苷配体进行化学修饰，可以利用DC-SIGN甘露糖结合位点附近的铵结合区，从而合成了D-SIGN的拟糖拮抗剂（化合物16）。对相关凝集素langerin具有前所未有的亲和力和选择性。在这里，提出了拟双金刚烷衍生物作为DC-SIGN配体的计算设计，其合成，作为DC-SIGN选择性拮抗剂的评估，DC-SIGN / 16配合物的生物物理表征以及配体活性的结构基础。 。在表征该配体的过程中，晶体内异常的桥连相互作用揭示了DC-SIGN碳水化合物识别域内的可塑性和潜在的二级结合位点。
• IMMUNOGENS FOR MENINGITIDIS-A VACCINES
  申请人：Oscarson Stefan

  公开号：US20090304734A1

  公开（公告）日：2009-12-10

  An oligosaccharide useful for a Meningitidis A vaccine contains a first mannose unit having a spacer in the alpha configuration at C-1, which spacer is capable of conjugating to a protein, and which is connected to a second mannose unit through a 1,6-linkage which connects C-6 of the first unit to C-1 of the second unit, wherein the 1,6-linkage comprises a phosphonate. Related methods of making such compounds, analogous compounds, or intermediates thereof are also disclosed.

  一种用于脑膜炎球菌A疫苗的寡糖包含第一个甘露糖单元，在C-1处具有α构型的间隔单元，该间隔单元能够与蛋白质结合，并通过将第一个单元的C-6连接到第二个单元的C-1的1,6-连接连接到第二个甘露糖单元，其中1,6-连接包含磷酸酯。还公开了制备这种化合物、类似化合物或其中间体的相关方法。