L-galactono-1,5-lactone | 124819-01-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-galactono-1,5-lactone
• 英文别名: (3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
• CAS: 124819-01-8
• 化学式: C₆H₁₀O₆
• 分子量: 178.142
• InChiKey: PHOQVHQSTUBQQK-RSJOWCBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  半乳糖酸內酯 在 Burkholderia multivorans ATCC 17616 amidohydrolase J_04915 作用下， 以 aq. buffer 为溶剂， 生成 L-galactono-1,5-lactone
  参考文献：
  名称：

  Discovery of an l-Fucono-1,5-lactonase from cog3618 of the Amidohydrolase Superfamily

  摘要：

  A member of the amidohydrolase superfamily, BmulJ_04915 from Burkholderia multivorans, of unknown function was determined to hydrolyze a series of sugar lactones: L-fiicono-1,4-lactone, n-arabino-1,4-lactone, L-xylono-1,4-lactone, D-lyxono-1,4-lactone, and L-galactono-1,4-lactone. The highest activity was shown for L-fucono-1,4-lactone with a k(cat) value of 140 s(-1) and a k(cat)/K-m value of 1.0 x 10(5) M-1 s(-1) at pH 8.3. The enzymatic product of an adjacent L-fucose dehydrogenase, BmulJ_04919, was shown to be L-fucono-1,5-lactone via nuclear magnetic resonance spectroscopy. L-Fucono-1,5-lactone is unstable and rapidly converts nonenzymatically to L-fucono-1,4-lactone. Because of the chemical instability of L-fiicono-1,5-lactone, 4-deoxy-L-fucono-1,5-lactone was enzymatically synthesized from 4-deoxy-L-fucose using L-fucose dehydrogenase. BmulJ-04915 hydrolyzed 4-deoxy-L-fucono-1,5-lactone with a k(cat) value of 990 s(-1) and a k(cat)/K-m value of 8.0 x 106 M-1 s(-1) at pH 7.1. The protein does not require divalent cations in the active site for catalytic activity. BmulJ_04915 is the second enzyme from cog3618 of the amidohydrolase superfamily that does not require a divalent metal for catalytic activity. BmulJ_04915 is the first enzyme that has been shown to catalyze the hydrolysis of either L-fucono-1,4-lactone or L-fucono-1,5-lactone. The structures of the fuconolactonase and the fucose dehydrogenase were determined by X-ray diffraction methods.

  DOI：

  10.1021/bi3015554

文献信息

• <scp>l</scp>-Galactose Metabolism in <i>Bacteroides vulgatus</i> from the Human Gut Microbiota
  作者：Merlin Eric Hobbs、Howard J. Williams、Brandan Hillerich、Steven C. Almo、Frank M. Raushel

  DOI：10.1021/bi500656m

  日期：2014.7.22

  A previously unknown metabolic pathway for the utilization of L-galactose was discovered in a prevalent gut bacterium, Bacteroides vulgatus. The new pathway consists of three previously uncharacterized enzymes that were found to be responsible for the conversion of L-galactose to D-tagaturonate. Bvu0219 (L-galactose dehydrogenase) was determined to oxidize L-galactose to L-galactono-1,5-lactone with k(cat) and k(cat)/K-m values of 21 s(-1) and 2.0 x 10(5) M-1 s(-1), respectively. The kinetic product of Bvu0219 is rapidly converted nonenzymatically to the thermodynamically more stable L-galactono-1,4-lactone. Bvu0220 (L-galactono-1,S-lactonase) hydrolyzes both the kinetic and thermodynamic products of Bvu0219 to L-galactonate. However, L-galactono-1,5-lactone is estimated to be hydrolyzed 300-fold faster than its thermodynamically more stable counterpart, L-galactono-1,4-lactone. In the final step of this pathway, Bvu0222 (L-galactonate dehydrogenase) oxidizes L-galactonate to D-tagaturonate with k(cat) and k(cat) /K-m values of 0.6 s(-1) and 1.7 x 10(4) M-1 s(-1), respectively. In the reverse direction, D-tagaturonate is reduced to L-galactonate with values of k(cat) and k(cat)/K-m of 90 s(-1) and 1.6 X 10(5) M-1 s(-1), respectively. D-Tagaturonate is subsequently converted to D-glyceraldehyde and pyruvate through enzymes encoded within the degradation pathway for D-glucuronate and D-galacturonate.
• COMPOSITIONS AND METHODS FOR ENHANCING PLANT GROWTH
  申请人：NOVOZYMES BIOAG A/S

  公开号：US20140087944A1

  公开（公告）日：2014-03-27

  Described herein are compositions comprising one or more gluconolactones for enhancing plant growth and methods for treating plants, plant parts, or soils with one or more gluconolactones for enhancing plant growth.