1,2,3,4,6-penta-O-acetyl-α,β-L-mannopyranose | 153830-26-3

• 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
• 英文名称: 1,2,3,4,6-penta-O-acetyl-α,β-L-mannopyranose
• 英文别名: 1,2,3,4,6-penta-O-acetyl-L-mannopyranose；[(2S,3S,4R,5R)-3,4,5,6-tetraacetyloxyoxan-2-yl]methyl acetate
• CAS: 153830-26-3
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: LPTITAGPBXDDGR-FIZKIRAISA-N

物化性质

• 沸点：
  434.8±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2,3,4,6-penta-O-acetyl-α,β-L-mannopyranose 在 苄胺 作用下， 以 四氢呋喃 为溶剂， 以1.62 g的产率得到[(2S,3S,4R,5R)-3,4,5-triacetyloxy-6-hydroxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Feedback Inhibition of Bacterial Nucleotidyltransferases by Rare Nucleotide l-Sugars Restricts Substrate Promiscuity

  摘要：

  DOI：

  10.1021/jacs.3c02319
• 作为产物：
  描述：

  L-altrose 生成 1,2,3,4,6-penta-O-acetyl-α,β-L-mannopyranose
  参考文献：
  名称：

  POZSGAY, VINCE;JENNINGS, HAROLD J., J. ORG. CHEM., 53,(1988) N 17, C. 4042-4052

  摘要：

  DOI：

文献信息

• [EN] DI- AND TRI-CATIONIC GLYCOSYLATED ANTITUMOR ETHER LIPIDS, L-GUCOSYLATED GAELS AND RHAMNOSE-LINKED GAELS AS CYTOTOXIC AGENTS AGAINST EPITHELIAL CANCER CELLS AND CANCER STEM CELLS<br/>[FR] ETHERS LIPIDIQUES ANTITUMORAUX GLYCOSYLÉS DI- ET TRICATIONIQUES, GAEL L-GLYCOSYLÉS ET GAEL LIÉS À DU RHAMNOSE UTILISABLES EN TANT QU'AGENTS CYTOTOXIQUES DIRIGÉS CONTRE DES CELLULES ÉPITHÉLIALES CANCÉREUSES ET DES CELLULES SOUCHES CANCÉREUSES
  申请人：UNIV MANITOBA

  公开号：WO2015179983A1

  公开（公告）日：2015-12-03

  Glycosylated Antitumor Ether Lipids (GAELs) kill cancer cells by a nonapoptotic pathway which is an attractive strategy to avoid resistance. To further optimize the antitumor effect, we prepared various analogs of di-, and tri-cationic GAEL analogs differing in the nature of the sugar (D-giucose or L-glucose), the anomeric linkage as well as position of the glycerolipid moiety. The di- and tri-cationic GAELs were synthesized and their in vitro anticancer properties were evaluated against drug resistant and aggressively growing cancer cell lines derived from human breast, prostate, pancreatic and ovarian cancers. The most potent dicationic GAEL analogs were also studied against cancer stem cells obtained from breast BT 474, prostate DU145 and ovarian A2780cp cell lines. Our results indicate that the number of positive charges, the position of the amino substituents and the nature of the sugar have significant effects on the anticancer activities of these compounds. The most active analog kill 50% of the cells at concentration range of 0.5-5μΜ and 90% of the cells at the concentration of 1-10μΜ depending on type of cancer cells.

  糖基化抗肿瘤醚脂质（GAELs）通过一种非凋亡途径杀灭癌细胞，这是一种吸引人的策略，可以避免抗药性。为了进一步优化抗肿瘤效果，我们制备了不同的双-和三-阳离子GAEL类似物，其糖的性质（D-葡萄糖或L-葡萄糖）、缩醛键以及甘油脂类团的位置不同。合成了双-和三-阳离子GAEL类似物，并评估了它们对人类乳腺、前列腺、胰腺和卵巢癌衍生的耐药和快速生长的癌细胞系的体外抗癌性能。最有效的双阳离子GAEL类似物也针对从乳腺BT 474、前列腺DU145和卵巢A2780cp细胞系中获得的癌干细胞进行了研究。我们的结果表明，阳离子数量、氨基取代物的位置和糖的性质对这些化合物的抗癌活性有显著影响。最活跃的类似物在浓度范围为0.5-5μΜ时杀死50%的细胞，在浓度为1-10μΜ时杀死90%的细胞，具体取决于癌细胞类型。
• [EN] NEW HYDROXYACID DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX DÉRIVÉS D'HYDROXYACIDE, LEUR PROCÉDÉ DE PRÉPARATION, ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SERVIER LAB

  公开号：WO2016207216A1

  公开（公告）日：2016-12-29

  Compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, R8, R14, A and n are as defined in the description. Medicaments.

  式(I)的化合物：其中R1、R2、R3、R4、R5、R6、R7、R8、R14、A和n的定义如描述所示。药物。
• Novel carbohydrate scaffolds. Assembly of a uridine–mannose scaffold based on tunicamycin
  作者：Domingos J Silva、Michael J Sofia

  DOI：10.1016/s0040-4039(99)02209-1

  日期：2000.2

  A disaccharide scaffold based on tunicamycin was synthesized from d-uridine and l-mannose. The key step in disaccharide assembly was a β-mannosylation performed using Crich’s modification of the sulfoxide glycosylation method. The scaffold described contains two orthogonal derivatization sites and will be used in the search for novel biologically active compounds.

  由衣尿苷和1-甘露糖合成了基于衣霉素的二糖支架。二糖组装的关键步骤是使用亚硫酸盐糖基化方法的Crich修饰法进行的β-甘露糖基化。所述支架包含两个正交衍生位点，将用于寻找新型生物活性化合物。
• Synthesis of<i>α</i>-<scp>L</scp>-Mannopyranosyl-containing Disaccharides and Phenols as Substrates for the<i>α</i>-<scp>L</scp>-Mannosidase Activity of Commercial Naringinase
  作者：Sachiko Esaki、Akemi Ohishi、Akiko Katsumata、Naoko Sugiyama、Shintaro Kamiya

  DOI：10.1271/bbb.57.2099

  日期：1993.1

  In order to clarify the substrate specificity of the α-L-mannosidase activity of naringinase (Sigma), the following disaccharides and phenol glycosides were freshly prepared: methyl 2-O-(α-L-mannopyranosyl)­β-D-glucoside (1), methyl 3-O-(α-L-mannopyranosyl)-α-D-glucoside (2), methyl 4-O-(α-L-mannopyranosyl)-α-D-glucoside (3), methyl 5-O-(α-L-mannopyranosyl)-β-D-glucoside (4), methyl 6-O-(α-L-mannopyranosyl)-α-D­glucoside (5), 6-O-(α-L-mannpyranosyl)-D-galactose (6), p-nitrophenyl α-L-mannoside (7), and 4-methyl umbelliferone α-L-mannoside (8).These compounds, except for 3 and 5, were hydrolyzed with naringinase.

  为了阐明枳椇苷酶（Sigma）α-L-甘露糖苷酶活性的底物特异性，制备了以下几种二糖和酚苷的新鲜样品：甲基 2-O-(α-L-甘露吡喃糖基)­β-D-葡糖苷（1）、甲基 3-O-(α-L-甘露吡喃糖基)-α-D-葡糖苷（2）、甲基 4-O-(α-L-甘露吡喃糖基)-α-D-葡糖苷（3）、甲基 5-O-(α-L-甘露吡喃糖基)-β-D-葡糖苷（4）、甲基 6-O-(α-L-甘露吡喃糖基)-α-D­葡糖苷（5）、6-O-(α-L-甘露吡喃糖基)-D-半乳糖（6）、对硝基苯 α-L-甘露糖苷（7）和 4-甲基伞形酮 α-L-甘露糖苷（8）。除了 3 和 5 之外，这些化合物均能被枳椇苷酶水解。
• Syntheses of l-Rhamnose-Linked Amino Glycerolipids and Their Cytotoxic Activities against Human Cancer Cells
  作者：Makanjuola Ogunsina、Pranati Samadder、Temilolu Idowu、Mark Nachtigal、Frank Schweizer、Gilbert Arthur

  DOI：10.3390/molecules25030566

  日期：——

  anticancer activity. The most potent analog synthesized, 3-amino-1-O-hexadecyloxy-2R-(O–α-l-rhamnopyranosyl)-sn- glycerol 3, demonstrated a potent antitumor effect against human cancer cell lines derived from breast, prostate, and pancreas. The activity observed was superior to that observed with clinical anticancer agents including cisplatin and chlorambucil. Moreover, like other GAELs, 3 induced cell death

  成功治疗癌症的一个主要障碍是临床上可用的药物无法杀死耐药癌细胞。我们最近发现了代谢稳定的基于 l-氨基葡萄糖的糖基化抗肿瘤醚脂质 (GAEL)，它们对化疗耐药的癌细胞具有细胞毒性。在没有市售的 l-葡糖胺的情况下，合成该化合物需要很多步骤，并且总收率很低。为了克服这一限制，开发了一种使用市售 l-糖（包括 l-鼠李糖和 l-葡萄糖）的简便合成程序，并测试了 l-GAEL 的抗癌活性。合成的最有效的类似物 3-amino-1-O-hexadecyloxy-2R-(O-α-l-rhamnopyranosyl)-sn-glycerol 3，对来源于乳腺癌、前列腺癌和前列腺癌的人类癌细胞系显示出有效的抗肿瘤作用。胰腺。观察到的活性优于使用包括顺铂和苯丁酸氮芥在内的临床抗癌剂观察到的活性。此外，与其他 GAEL 一样，3 通过非膜溶解半胱天冬酶非依赖性途径诱导细胞死亡。