(1S,2R)-1-(3-amino-6-methyl-1,2,4-triazin-5-yl)-1,2,3-propanetriol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: (1S,2R)-1-(3-amino-6-methyl-1,2,4-triazin-5-yl)-1,2,3-propanetriol
• 英文别名: 3-amino-5-<(D-threo)-1,2,3-trihydroxypropyl>-6-methyl-1,2,4-triazine；3-Amino-5-(D-erythro-1,2,3-trihydroxypropyl)-6-methyl-1,2,4-triazine；(1S,2R)-1-(3-amino-6-methyl-1,2,4-triazin-5-yl)propane-1,2,3-triol
• 化学式: C₇H₁₂N₄O₃
• 分子量: 200.197
• InChiKey: ZCIOGLSBKMPKDI-INEUFUBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [(4R,5S)-5-(3-amino-6-methyl-1,2,4-triazin-5-yl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以29%的产率得到(1S,2R)-1-(3-amino-6-methyl-1,2,4-triazin-5-yl)-1,2,3-propanetriol
  参考文献：
  名称：

  Synthesis of 1-deoxy-d-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate

  摘要：

  1-Deoxy-D-erythro-hexo-2,3-diulose (1-DG) was prepared by the reaction of ethoxyvinyllithium with an erythrono-lactone derivative. Characterization by H-1 and C-13 NMR spectroscopy and NOE difference experiments revealed the C-2(5)-chair beta -pyranose as the major isomer in solution. Experiments assessing browning and polymerization reactivity proved I-DG to be a much more potent protein modifier than 3-deoxy-D-erythro-hexos-2-ulose. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00219-6

文献信息

• The detection of some dicarbonyl intermediates arising from the degradation of Amadori compounds (the Maillard reaction)
  作者：Jan Hirsch、Valeri V. Mossine、Milton S. Feather

  DOI：10.1016/0008-6215(95)00114-9

  日期：1995.8

  mixture had little effect on the ratio or the nature of the dicarbonyl compounds produced. This represents an unusual situation, wherein two different dicarbonyl intermediates (one produced, presumably, as a result of initial 1,2-enolization and the other, presumably as a result of 2,3-enolization) were identified in the same Maillard reaction mixture.

  摘要三种Amadori化合物N-（1-脱氧-d-果糖-1-基）-甘氨酸（1），N ϵ-（1-脱氧-d-果糖-1-基）-Nα-甲酰基-l-将赖氨酸（2）和N，N-二-（1-脱氧-d-果糖-1-基）-甘氨酸（3）在pH值对应于取代氨基的pKa的缓冲溶液中孵育（37°C）氨基胍存在下的基团。捕集到的二羰基中间体作为稳定的三嗪衍生物（6a，6b和7）被捕获，并根据反应时间测量其收率。衍生自1-脱氧-2,3- d-赤藓基己二糖（“ 1-deoxyglucosone”，5）和3-deoxy- d-赤-己基-2-ulose（“ 3-deoxyglucosone”，4）的三嗪经GLC检测为三甲基甲硅烷基衍生物，并与真实标准品和GLC-MS进行了明确鉴定。改变温育混合物的pH对所产生的二羰基化合物的比例或性质几乎没有影响。这代表了一种不寻常的情况，其中在同一美拉德反应混合物中鉴定出两种不同的二羰基中间体（一种可能是由于最初的1
• Hirsch, Jan; Petrakova, Eva; Feather, Milton S., Journal of Carbohydrate Chemistry, 1995, vol. 14, # 8, p. 1179 - 1186
  作者：Hirsch, Jan、Petrakova, Eva、Feather, Milton S.

  DOI：——

  日期：——
• Synthesis of 1-deoxy-d-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate
  作者：Marcus A. Glomb、Christoph Pfahler

  DOI：10.1016/s0008-6215(00)00219-6

  日期：2000.11

  1-Deoxy-D-erythro-hexo-2,3-diulose (1-DG) was prepared by the reaction of ethoxyvinyllithium with an erythrono-lactone derivative. Characterization by H-1 and C-13 NMR spectroscopy and NOE difference experiments revealed the C-2(5)-chair beta -pyranose as the major isomer in solution. Experiments assessing browning and polymerization reactivity proved I-DG to be a much more potent protein modifier than 3-deoxy-D-erythro-hexos-2-ulose. (C) 2000 Elsevier Science Ltd. All rights reserved.