sodium salt of 2-deoxy-2-sulfoamino-β-D-glucopyranose | 69558-06-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: sodium salt of 2-deoxy-2-sulfoamino-β-D-glucopyranose
• 英文别名: methyl 2-deoxy-2-sulfonatoamino-α-D-glucopyranoside sodium salt；methyl-(2-sulfoamino-2-deoxy-α-D-glucopyranoside); sodium-salt；Methyl-(2-sulfoamino-2-desoxy-α-D-glucopyranosid); Natrium-Salz
• CAS: 69558-06-1
• 化学式: C₇H₁₄NO₈S*Na
• 分子量: 295.246
• InChiKey: MXISPVUYMUYWFP-XOOUXKSCSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -6.51
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  148.38
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  methyl 2-amino-2-deoxy-α-D-glucopyranoside 在 三甲基铵三氧化硫共聚物 、 三乙胺 作用下， 以 水 为溶剂， 反应 1.0h， 以40 mg的产率得到sodium salt of 2-deoxy-2-sulfoamino-β-D-glucopyranose
  参考文献：
  名称：

  Glycans as Ligands in Bioinorganic Chemistry. Probing the Interaction of a Trinuclear Platinum Anticancer Complex with Defined Monosaccharide Fragments of Heparan Sulfate

  摘要：

  We report herein a detailed NMR study of the aquation and subsequent covalent binding of the trinuclear clinical agent [{trans-PtCl((NH3)-N-15)(2)}(2){mu-trans-Pt((NH3)-N-15)(2)((NH2)-N-15(CH2)(6)(NH2)-N-15)(2)}](4+) (1, 1,0,1/t,t,t or Triplatin) with three d-glucosamine residues containing varied O-sulfate and N-sulfate or N-acetyl substitutions, which represent monosaccharide fragments present within the repeating disaccharide sequences of cell surface heparan sulfate (HS). The monosaccharides GlcNS(6S), GlcNS, and GlcNAc(6S) were synthesized in good yield from a common 4,6-diol alpha-methyl glucopyranoside intermediate. The reactions of N-15-1 with sodium sulfate, GlcNS(6S), GlcNS, and GlcNAc(6S) were followed by 2D [H-1,N-15] heteronuclear single quantum coherence (HSQC) NMR spectroscopy using conditions (298 K, pH approximate to 5.4) similar to those previously used for other anionic systems, allowing for a direct comparison. The equilibrium constants (pK(1)) for the aquation of 1 in the presence of GlcNS(6S) and GlcNS were slightly higher compared to that of the aquation in a sulfate solution, while a comparable pK(1) value was observed in the presence of GlcNAc(6S). A comparison of the rate constants for sulfate displacement of the aqua ligand showed preferential binding to 2-N-sulfate compared to 6-O-sulfate but a more rapid liberation. For disulfated GlcNS(6S), equilibrium conditions were achieved rapidly (9 h) and strongly favored the dichloro form, with <2% sulfato species observed. The value of k(L1) was up to 15-fold lower than that for binding to sulfate, whereas the rate constant for the reverse ligation (k(-L1)) was comparable. Equilibrium conditions were achieved much more slowly (similar to 100 h) for the reactions of 1 with GlcNS and GlcNAc(6S), attributed to covalent binding also to the N-donor of the sulfamate (GlcNS) group and the O-donor of the N-acetyl [GlcNAc(6S)] group. The rate constants (k(L2)) were 20-40-fold lower than that for binding to the 2-N- or 6-O-sulfate, but the binding was less reversible, so that their equilibrium concentrations (5-8%) were comparable to the 2-N- or 6-O-sulfate-bound species. The results emphasize the relevance of glycans in bioinorganic chemistry and underpin a fundamental molecular description of the HS-Pt interactions that alter the profile of platinum agents from cytotoxic to metastatic in a systematic manner.

  DOI：

  10.1021/acs.inorgchem.8b03035

文献信息

• Derivatives of D-Glucose Containing the Sulfoamino Group¹
  作者：M. L. Wolfrom、R. A. Gibbons、A. J. Huggard

  DOI：10.1021/ja01575a058

  日期：1957.9