(2',2',5',5'-tetramethylpyrroline-1'-oxyl-3'-methyl)-O-β-D-glucoside | 1582289-13-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2',2',5',5'-tetramethylpyrroline-1'-oxyl-3'-methyl)-O-β-D-glucoside
• 英文别名: 3-hydroxymethyl-DPRO O-β-D-glucoside
• CAS: 1582289-13-1
• 化学式: C₁₅H₂₆NO₇
• 分子量: 332.374
• InChiKey: AOBXNVVFILCGLD-UJPOAAIJSA-N

反应信息

• 作为产物：
  描述：

  3-羟基甲基-2,2,5,5-四甲基吡咯啉-N-氧自由基 、 per-O-benzoyl-α-D-glucopyranosyl bromide 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以52.5%的产率得到(2',2',5',5'-tetramethylpyrroline-1'-oxyl-3'-methyl)-O-β-D-glucoside
  参考文献：
  名称：

  Evaluation of glucose-linked nitroxide radicals for use as an in vivo spin-label probe

  摘要：

  In vivo incorporation and reduction abilities of 4-carboxy-2,2,6,6-tetramethylpiperidine-1-oxyl (4-carboxy-TEMPO) (1), 3-carboxy-2,2,5,5-tetramethylpyrroline-1-oxyl (3-carboxy-dehydro-PROXYL, 3-carboxy-DPRO) (2), 4-hydroxy-TEMPO and 3-hydroxymethyl-DPRO O-beta-o-glucosides (3 and 5), and newly designed forms of 6-O-(TEMPO-4-carbonyl and DPRO-3-carbonyl)-D-glucose (4 and 6) were evaluated using white radish sprouts. For each of these compounds, electron spin resonance (ESR) spectrometry was used to measure two effects: the rate of in vitro reduction via the addition of ascorbic acid; and, the rate of successful incorporation into radish sprouts for a reduction to the corresponding hydroxyl amine. DPRO-radicals 2, 5, and 6 were detected significantly more than TEMPO-radicals 1, 3, and 4 in vitro and in vivo for both experiments. Four glucose-linked nitroxide radicals were reduced faster than the glucose-non-linked ones in the in vitro experiment, but were nonetheless detected more each time in radish sprouts due to the absorbability. Glucose ester-linked radicals 4 and 6 were detected more than glycosides 3 and 5, which suggests that glucose ester-linked DPRO-radical 6 is the best for use as a spin-label probe that a plant will incorporate. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.01.047