6-α-maltosyl ascorbic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-α-maltosyl ascorbic acid
• 英文别名: (2R)-2-[(1S)-2-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-1-hydroxyethyl]-3,4-dihydroxy-2H-furan-5-one
• 化学式: C₁₈H₂₈O₁₆
• 分子量: 500.411
• InChiKey: LIVRQHJHRFRCAX-XXQBTRJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  266
• 氢给体数：
  10
• 氢受体数：
  16

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  维生素 C	ascorbic acid	50-81-7	C6H8O6	176.126
  直链淀粉	maltotriose	9005-82-7	C18H32O16	504.442

反应信息

• 作为产物：
  描述：

  直链淀粉 、 维生素 C 在 Bacillus stearothermophilus maltogenic amylase 作用下， 以 水 为溶剂， 反应 48.0h， 生成 6-O-α-D-Glucopyranosyl-L-ascorbic acid 、 6-α-maltosyl ascorbic acid
  参考文献：
  名称：

  Modification of Ascorbic Acid Using Transglycosylation Activity of Bacillus stearothermophilus Maltogenic Amylase to Enhance Its Oxidative Stability

  摘要：

  Ascorbic acid (1), a natural antioxidant, was modified by employing transglycosylation activity of Bacillus stearothermophilus maltogenic amylase with maltotriose and acarbose as donor molecules to enhance its oxidative stability. The transglycosylation reaction with maltotriose as donor created mono- and di-glycosyl transfer products with an (alpha-(1,6)-glycosidic linkage. In addition, two acarviosine-glucosyl transfer products were generated when transglycosylation was performed with acarbose as a donor. All transfer products were observed by TLC and HPLC, and purified by Q-sepharose anion exchange and Biogel P-2 gel permeation chromatographies. LC/MS and C-13 NMR analyses revealed that the structures of the transfer products were 6-O-alpha-D-glucosyl- (2) and 6-O-alpha-D-maltosyl-ascorbic acids (3) in the reaction of maltotriose, and 6-O-alpha-acarviosine-D-glucosyl- (4) and 2-O-alpha-acarviosine-D-glucosyl ascorbic acids (5) in the reaction of acarbose. The stability of the transglycosylated ascorbic acid derivatives was greatly enhanced against oxidation by Cu2+ ion and ascorbate oxidase. Among them, compound 3 proved to be the most stable against in vitro oxidation. The antioxidant effects of glycosyl-derivatives of ascorbic acid on the lipid oxidation in cooked chicken breast meat patties indicated that they had antioxidant activities similar to that of ascorbic acid. It is suggested that the transglycosylated ascorbic acids can possibly be applied as effective antioxidants with improved stability in food, cosmetic, and other applications.

  DOI：

  10.1021/jf011550z

文献信息

• Modification of Ascorbic Acid Using Transglycosylation Activity of <i>Bacillus stearothermophilus</i> Maltogenic Amylase to Enhance Its Oxidative Stability
  作者：Hee-Kyung Bae、Soo-Bok Lee、Cheon-Seok Park、Jae-Hoon Shim、Hye-Young Lee、Myo-Jeong Kim、Jin-Sook Baek、Hoe-Jin Roh、Jin-Hwan Choi、Eun-Ok Choe、Dong-Uk Ahn、Kwan-Hwa Park

  DOI：10.1021/jf011550z

  日期：2002.5.1

  Ascorbic acid (1), a natural antioxidant, was modified by employing transglycosylation activity of Bacillus stearothermophilus maltogenic amylase with maltotriose and acarbose as donor molecules to enhance its oxidative stability. The transglycosylation reaction with maltotriose as donor created mono- and di-glycosyl transfer products with an (alpha-(1,6)-glycosidic linkage. In addition, two acarviosine-glucosyl transfer products were generated when transglycosylation was performed with acarbose as a donor. All transfer products were observed by TLC and HPLC, and purified by Q-sepharose anion exchange and Biogel P-2 gel permeation chromatographies. LC/MS and C-13 NMR analyses revealed that the structures of the transfer products were 6-O-alpha-D-glucosyl- (2) and 6-O-alpha-D-maltosyl-ascorbic acids (3) in the reaction of maltotriose, and 6-O-alpha-acarviosine-D-glucosyl- (4) and 2-O-alpha-acarviosine-D-glucosyl ascorbic acids (5) in the reaction of acarbose. The stability of the transglycosylated ascorbic acid derivatives was greatly enhanced against oxidation by Cu2+ ion and ascorbate oxidase. Among them, compound 3 proved to be the most stable against in vitro oxidation. The antioxidant effects of glycosyl-derivatives of ascorbic acid on the lipid oxidation in cooked chicken breast meat patties indicated that they had antioxidant activities similar to that of ascorbic acid. It is suggested that the transglycosylated ascorbic acids can possibly be applied as effective antioxidants with improved stability in food, cosmetic, and other applications.