2-脱氧肌糖 | 22389-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-脱氧肌糖
• 英文名称: 2-deoxy-scyllo-inosose
• 英文别名: DOI；(2R,3S,4R,5S)-2,3,4,5-tetrahydroxycyclohexan-1-one
• CAS: 22389-01-1；60802-52-0；61914-09-8；78963-40-3
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: GZYCZKBRQBKGJW-YGIVHSIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-脱氧肌糖 、 4-硝基苯基-D-吡喃葡糖苷 在 β-galactosidase 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以19.7 mg的产率得到Galβ1->4DOI
  参考文献：
  名称：

  Evaluation and Comparison of the Antioxidative Potency of Various Carbohydrates Using Different Methods

  摘要：

  A detailed analysis of the antioxidative activity of 12 carbohydrates including chondroitin sulfate, fucoidan, agaro-oligosaccharide, 2-deoxy-scyllo-inosose (DOI), Gal beta 1-4DOI, D-glucuronic acid, chitobiose, D-mannosamine, D-galactosamine, D-glucosamine, heparin, and colominic acid was performed using four established methods: 2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay, ferric reducing antioxidant power (FRAP) assay, superoxide dismutase (SOD) activity assay, and the deoxyribose method. Ascorbic acid and/or catechin were used as positive standards. In the DPPH radical scavenging activity measurements, fucoidan, DOI, and Ga1 beta 1-4DOI showed remarkable levels of activity, although at lower levels than ascorbic acid. The SOD assay revealed that DOI, Gal beta 1-4DOI, and agaro-oligosaccharide had high antioxidant activity, with DOI and Gal beta 1-4DOI notably showing almost half of the antioxidative potency of ascorbic acid. Using the deoxyribose method, chitobiose and heparin showed the highest hydroxyl radical scavenging activity, followed by chondroitin sulfate, colominic acid, Gal beta 1-4DOI, and D-glucosamine. Given that 11 of the carbohydrates analyzed share a common structure, agaro-oligosaccharide being the exception, we propose from our current results that at least one amino, carboxyl, carbonyl, or sulfonyl group is required, but is not in itself sufficient, for carbohydrates to function as antioxidants.

  DOI：

  10.1021/jf804020u
• 作为产物：
  描述：

  (1α,2β,3α,4β,5α)-1,2,3,4,5-Cyclohexanpentol 在 铂 氧气 作用下， 以 水 为溶剂， 生成 2-脱氧肌糖
  参考文献：
  名称：

  Untersuchungen zum Wirkungsmechanismus glykosidspaltender Enzyme, VIII. Anzahl der aktiven Zentren der β - Glucosidasen A und B aus dem Süßmandel-Emulsin durch Fluoreszenzmessungen

  摘要：

  DOI：

  10.1515/bchm2.1974.355.1.617

文献信息

• Untersuchungen zum Wirkungsmechanismus glykosidspaltender Enzyme, VIII. Anzahl der aktiven Zentren der β - Glucosidasen A und B aus dem Süßmandel-Emulsin durch Fluoreszenzmessungen
  作者：Günter Legler、Felix Witassek

  DOI：10.1515/bchm2.1974.355.1.617

  日期：——
• Evaluation and Comparison of the Antioxidative Potency of Various Carbohydrates Using Different Methods
  作者：Katsumi Ajisaka、Sayuri Agawa、Satomi Nagumo、Keisuke Kurato、Tatsuya Yokoyama、Kumiko Arai、Tatsuo Miyazaki

  DOI：10.1021/jf804020u

  日期：2009.4.22

  A detailed analysis of the antioxidative activity of 12 carbohydrates including chondroitin sulfate, fucoidan, agaro-oligosaccharide, 2-deoxy-scyllo-inosose (DOI), Gal beta 1-4DOI, D-glucuronic acid, chitobiose, D-mannosamine, D-galactosamine, D-glucosamine, heparin, and colominic acid was performed using four established methods: 2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay, ferric reducing antioxidant power (FRAP) assay, superoxide dismutase (SOD) activity assay, and the deoxyribose method. Ascorbic acid and/or catechin were used as positive standards. In the DPPH radical scavenging activity measurements, fucoidan, DOI, and Ga1 beta 1-4DOI showed remarkable levels of activity, although at lower levels than ascorbic acid. The SOD assay revealed that DOI, Gal beta 1-4DOI, and agaro-oligosaccharide had high antioxidant activity, with DOI and Gal beta 1-4DOI notably showing almost half of the antioxidative potency of ascorbic acid. Using the deoxyribose method, chitobiose and heparin showed the highest hydroxyl radical scavenging activity, followed by chondroitin sulfate, colominic acid, Gal beta 1-4DOI, and D-glucosamine. Given that 11 of the carbohydrates analyzed share a common structure, agaro-oligosaccharide being the exception, we propose from our current results that at least one amino, carboxyl, carbonyl, or sulfonyl group is required, but is not in itself sufficient, for carbohydrates to function as antioxidants.