α,β-D-mannopyranosyl-amine | 43179-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α,β-D-mannopyranosyl-amine
• 英文别名: D-mannopyranosyl amine；D-Mannopyranosylamine；(3S,4S,5S,6R)-2-amino-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 43179-10-8
• 化学式: C₆H₁₃NO₅
• 分子量: 179.173
• InChiKey: WCWOEQFAYSXBRK-QTVWNMPRSA-N

物化性质

• 沸点：
  416.4±45.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  12
• 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：
  116
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α,β-D-mannopyranosyl-amine 在 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 potassium bromide 作用下， 以 四氢呋喃 、 碳酸氢钠 为溶剂， 生成 N-(fluoren-9-ylmethoxycarbonyl)-β-D-mannopyranosyl uronic acid
  参考文献：
  名称：

  N-（氟-9-基甲氧基羰基）甘露糖基氨基糖醛酸的合成

  摘要：

  描述了适于固相合成的10种N-（氟-9-基甲氧基羰基）甘露糖基氨基糖醛酸的合成。一般的合成策略包括首先引入受保护的胺，然后对C-6羟基进行TEMPO选择性氧化，得到相应的Fmoc保护的糖氨基酸。胺的掺入可通过游离糖的氨解或糖基叠氮化物的还原来完成。该反应可以以多克级进行，从而提供了访问独特单体单元的途径，以便将来将其并入组合文库合成中。

  DOI：

  10.1016/j.carres.2003.10.018
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-α-D-叠氮化吡喃甘露糖 在 镍 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 α,β-D-mannopyranosyl-amine
  参考文献：
  名称：

  N-（氟-9-基甲氧基羰基）甘露糖基氨基糖醛酸的合成

  摘要：

  描述了适于固相合成的10种N-（氟-9-基甲氧基羰基）甘露糖基氨基糖醛酸的合成。一般的合成策略包括首先引入受保护的胺，然后对C-6羟基进行TEMPO选择性氧化，得到相应的Fmoc保护的糖氨基酸。胺的掺入可通过游离糖的氨解或糖基叠氮化物的还原来完成。该反应可以以多克级进行，从而提供了访问独特单体单元的途径，以便将来将其并入组合文库合成中。

  DOI：

  10.1016/j.carres.2003.10.018

文献信息

• Platinum complexes of polyhydroxylated alkylamines and
  申请人：American Cyanamid Company

  公开号：US04587331A1

  公开（公告）日：1986-05-06

  Platinum complexes of polyhydroxylated alkylamines and 2-polyhydroxylated alkyl-1,2-diaminoethanes useful for inducing regression and/or palliation of cancer diseases in mammals.

  聚羟基烷胺和2-聚羟基烷基-1,2-二胺乙烷的铂配合物可用于诱导哺乳动物癌症的退缩和/或缓解。
• Platinum complexes
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0186085A2

  公开（公告）日：1986-07-02

  Platinum complexes useful for inducing regression and/or palliation of cancer diseases in mammals

  可诱导哺乳动物癌症疾病消退和/或缓解的铂复合物
• Preparation of S‐ and N‐Linked Glycosylated Amino Acid Building Blocks for Solid‐phase Glycopeptide Library Synthesis*
  作者：C. Maljaars、Koen Halkes、Wim de Oude、Seléne van der Poel、Niels Pijnenburg、Johannis Kamerling

  DOI：10.1081/car-200066915

  日期：2005.8.1

  A general route for the preparation of 1,2-trans-linked S-glycosylated amino acid building blocks by a Lewis-acid-promoted condensation of peracetylated glycosyl donors and N-alpha-Fmoc-Cys-OH, in good overall yield, is described. In addition, a short and time-efficient route was applied for the synthesis of N-glycosylated amino acid building blocks in good overall yields by coupling unprotected glycosylamines and N-alpha-Fmoc-Asp(OH)-(OBu)-Bu-t using TBTU activation.
• The Synthesis and Investigation of the Liquid-Crystalline Phase Behaviour of a Series of N,N-bis(1-deoxy-<i>D</i>-mannitol-1-yl)-alkamides
  作者：D. F. Ewing、P. Letellier、G. Mackenzie、G. H. Mehl、J. W. Goodby

  DOI：10.1080/10587250108028682

  日期：2001.8
• Synthesis and immunostimulatory activity of sugar-conjugated TLR7 ligands
  作者：Akihito Baba、Masahiro Wakao、Hiroyuki Shinchi、Michael Chan、Tomoko Hayashi、Shiyin Yao、Howard B. Cottam、Dennis A. Carson、Yasuo Suda

  DOI：10.1016/j.bmcl.2019.126840

  日期：2020.2

  Toll-like receptors (TLRs) are a type of pattern recognition receptors (PRRs), which are activated by recognizing pathogen-associated molecular patterns (PAMPs). The activation of TLRs initiates innate immune responses and subsequently leads to adaptive immune responses. TLR agonists are effective immuomodulators in vaccine adjuvants for infectious diseases and cancer immunotherapy. In exploring hydrophilic small molecules of TLR7 ligands using the cell-targeted property of a vaccine adjuvant, we conjugated 1V209, a small TLR7 ligand molecule, with various low or middle molecular weight sugar molecules that work as carriers. The sugar-conjugated 1V209 derivatives showed increased water solubility and higher immunostimulatory activity in both mouse and human cells compared to unmodified 1V209. The improved immunostimulatory potency of sugar-conjugates was attenuated by an inhibitor of endocytic process, cytochalasin D, suggesting that conjugation of sugar moieties may enhance the uptake of TLR7 ligand into the endosomal compartment. Collectively our results support that sugar-conjugated TLR7 ligands are applicable to novel drugs for cancer and vaccine therapy.