4-deoxy-D-mannopyranoside | 24707-42-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 4-deoxy-D-mannopyranoside
• 英文别名: 4-deoxy-mannose；D-lyxo-4-deoxy-hexose；ξ-D-lyxo-4-deoxy-hexopyranose；4-deoxy-D-mannose；(3S,4S,6S)-6-(hydroxymethyl)oxane-2,3,4-triol
• CAS: 24707-42-4
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: HDEMQQHXNOJATE-NNXAEHONSA-N

物化性质

• 沸点：
  366.9±42.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-deoxy-D-mannopyranoside 在 dowex 50Wx₈ 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 2,3-O-isopropylidene-4-deoxy-α-D-lyxo-hexopyranoside
  参考文献：
  名称：

  The electron-releasing homoconjugated carbonyl group. Application to the total syntheses of 3-deoxy-, 4-deoxy-hexose, lividosamine and derivatives

  摘要：

  DOI：

  10.1016/s0040-4039(00)70712-x
• 作为产物：
  描述：

  1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 4-deoxy-D-mannopyranoside
  参考文献：
  名称：

  A novel synthesis of 4-deoxy-d-lyxo-hexose (“4-deoxy-d-mannose”) from 1,6-anhydro-3,4-dideoxy-β-d-glycero-hex-3-enopyranose-2-ulose (levoglucosenone)

  摘要：

  DOI：

  10.1016/0008-6215(93)84046-9

文献信息

• Chemoenzymatic synthesis of sialosides containing C7-modified sialic acids and their application in sialidase substrate specificity studies
  作者：Zahra Khedri、Yanhong Li、Saddam Muthana、Musleh M. Muthana、Ching-Wen Hsiao、Hai Yu、Xi Chen

  DOI：10.1016/j.carres.2014.02.021

  日期：2014.5

  chemoenzymatic synthesis of α2-3- and α2-6-linked sialyl para-nitrophenyl galactosides in which the C7-hydroxyl group in sialic acid (N-acetylneuraminic acid, Neu5Ac, or 2-keto-3-deoxynonulosonic acid, Kdn) was systematically substituted by -F, -OMe, -H, and -N3 groups. Substrate specificity study of bacterial and human sialidases using the obtained sialoside library containing C7-modified sialic acids showed

  唾液酸苷中唾液酸甘油侧链的修饰通过唾液酸结合蛋白和唾液酸酶来调节其识别。然而，有限的工作集中在具有C7修饰的唾液酸的唾液酸化物的合成和功能研究上。在这里，我们报告化学合成C4修饰的ManNAc和甘露糖及其作为唾液酸前体在高效一锅三酶系统中化学合成α2-3和α2-6连接的唾液酸对硝基苯基半乳糖苷的唾液酸前体的应用。唾液酸中的C7-羟基（N-乙酰神经氨酸，Neu5Ac或2-酮-3-脱氧壬二酸，Kdn）被-F，-OMe，-H和-N3系统取代。使用获得的含有C7修饰的唾液酸的唾液酸文库，对细菌和人唾液酸酶的底物特异性研究表明，含有C7-脱氧Neu5Ac的唾液酸苷是所有测试的细菌唾液酸酶（而非人NEU2）的选择性底物。从唾液酸酶底物特异性获得的信息可用于指导对细菌唾液酸酶具有选择性的新抑制剂的设计。
• Hydrolytic Activity of<i>α</i>-Mannosidase against Deoxy Derivatives of<i>p</i>-Nitrophenyl<i>α</i>-<scp>d</scp>-Mannopyranoside
  作者：Toshiyuki Nishio、Yayoi Miyake、Hitomi Tsujii、Wataru Hakamata、Kazunari Kadokura、Tadatake Oku

  DOI：10.1271/bbb.60.2038

  日期：1996.1

  Deoxy derivatives of p-nitrophenyl (PNP) α-d-mannopyranoside, PNP 2-deoxy-α-d-arabino-hexopyranoside, 3-deoxy-α-d-arabino-hexopyranoside, 4-deoxy-α-d-lyxo-hexopyranoside, and α-d-rhamnopyranoside, were synthesized and hydrolytic activities of jack bean and almond α-mannosidases against them were investigated. These α-mannosidases scarcely acted on the 2-, 3-, and 4-deoxy derivatives, while the 6-deoxy one was hydrolyzed by the enzymes as fast as PNP α-d-mannopyranoside, which is a common substrate for α-mannosidase. These results indicate that the hydroxyl groups at C-2, 3, and 4 of the mannopyranoside are necessary to be recognized as a substrate by these enzymes, while that at C-6 does not have so a crucial role in substrate discrimination. Values of Km and Vmax of the enzymes on the hydrolysis of PNP α-d-rhamnopyranoside were obtained from kinetic studies.

  合成了对硝基苯（PNP）α-d-吡喃甘露糖苷的脱氧衍生物、PNP 2-脱氧-α-d-阿拉伯诺-吡喃己糖苷、3-脱氧-α-d-阿拉伯诺-吡喃己糖苷、4-脱氧-α-d-来苏诺-吡喃己糖苷和α-d-鼠李糖苷，并研究了千层豆和杏仁α-甘露糖苷酶对它们的水解活性。这些α-甘露糖苷酶几乎不作用于 2-、3-和 4-脱氧衍生物，而 6-脱氧衍生物被酶水解的速度与 PNP α-d-吡喃甘露糖苷一样快，后者是α-甘露糖苷酶的常见底物。这些结果表明，曼吡喃糖苷的 C-2、3 和 4 处的羟基是这些酶识别底物的必要条件，而 C-6 处的羟基在底物鉴别中并没有如此关键的作用。动力学研究得出了酶水解 PNP α-d-rhamnopyranoside 的 Km 值和 Vmax 值。
• TOLL-LIKE RECEPTOR 9 AGONISTS
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：EP2017281A1

  公开（公告）日：2009-01-21

  The present invention provides TLR9 agonists comprising, as an active ingredient, a compound represented by formula (I): (wherein a represents 0 or 1; n represents an integer of 0 to 2; m represents an integer of 0 to 5; X1 and X2 each independently represent a hydrogen atom or hydroxy; Y represents an oxygen atom or a sulfur atom; -Q1-represents -O- or the like; -Q2- represents -O- or the like; -Z- represents -O- or the like; R1, R3 and R4 each independently represent hydroxy or the like; R2 and R5 each independently represent a hydrogen atom, hydroxy or the like; and A represents 6-aminopurin-9-yl or the like) or a pharmaceutically acceptable salt thereof, and the like.

  本发明提供了 TLR9 激动剂，其活性成分包括式 (I) 所代表的化合物： (其中a代表0或1；n代表0至2的整数；m代表0至5的整数；X1和X2各自独立地代表氢原子或羟基；Y代表氧原子或硫原子；-Q1-代表-O-或类似物；-Q2-代表-O-或类似物；-Z-代表-O-或类似物；R1、R3和R4各自独立地代表羟基或类似物；R2和R5各自独立地代表氢原子、羟基或类似物；A代表6-氨基嘌呤-9-基或类似物）或其药学上可接受的盐等。
• Scope and limitations of the aldol condensation catalyzed by immobilized acylneuraminate pyruvate lyase
  作者：Claudine Augé、Bénédicte Bouxom、Bertrand Cavayé、Christine Gautheron

  DOI：10.1016/s0040-4039(00)99652-7

  日期：1989.1
• AUGE, CLAUDINE;BOUXOM, BENEDICTE;CAVAYE, BERTRAND;GAUTHERON, CHRISTINE, TETRAHEDRON LETT., 30,(1989) N7, C. 2217-2220
  作者：AUGE, CLAUDINE、BOUXOM, BENEDICTE、CAVAYE, BERTRAND、GAUTHERON, CHRISTINE

  DOI：——

  日期：——