L-fuconolactone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-fuconolactone
• 英文别名: L-Fucono-1,5-lactone；(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-one
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: ZVAHHEYPLKVJSO-RSJOWCBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 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：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-fuconolactone 以 aq. buffer 为溶剂， 生成 6-脱氧-L-半乳糖酸内酯
  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
• 作为产物：
  描述：

  6-脱氧-L-半乳糖酸内酯 在 Burkholderia multivorans ATCC 17616 amidohydrolase J_04915 作用下， 以 aq. buffer 为溶剂， 生成 L-fuconolactone
  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

• Iron-catalysed chemo-selective oxidation of unprotected sugars: application for the competitive oxidation of pentoses from a sugar mixture
  作者：David Branquet、Mohamed Vall Sidi Boune、Nicolas Hucher、Catherine Taillier、Vincent Dalla、Sébastien Comesse、Laure Benhamou

  DOI：10.1039/d2gc02606f

  日期：——

  developed to oxidise aldo-hexoses and -pentoses into sugar lactones using different acceptors. The transformation occurs on unprotected sugars with complete chemo-selectivity for the anomeric position. An application for the competitive oxidation of pentose from a mixture of C5 and C6 sugars is also reported. Finally, we managed to perform the oxidation of xylose with only an equimolar amount of a carefully

  开发了一种铁催化的转移氢化方法，以使用不同的受体将己醛糖和戊糖氧化成糖内酯。转化发生在对异头位置具有完全化学选择性的未保护糖上。还报道了从 C5 和 C6 糖的混合物中竞争性氧化戊糖的应用。最后，我们设法仅用等摩尔量的精心选择的受体进行木糖的氧化，在不影响平衡转变的情况下大大提高了转化的可持续性。
• Fermentation process for producing monosaccharides in free form from nucleotide-activated sugars
  申请人：Jennewein Biotechnologie GmbH

  公开号：EP3050973A1

  公开（公告）日：2016-08-03

  The present invention relates to a process for producing a monosaccharide, e.g. L-fucose, in free form using a microbioal fermentation process. The used microorganism exhibits hydrolase activity on nucleotide-activated sugars and releases the monosaccharide in an unmodified free form. The free monosaccharide is retrieved from the supernatant of the cultivated microorganism.

  本发明涉及一种利用微生物醛发酵工艺生产游离态单糖（如 L-岩藻糖）的工艺。使用的微生物对核苷酸激活的糖具有水解酶活性，并以未修饰的游离形式释放单糖。游离单糖从培养微生物的上清液中提取。
• Horiuchi, Tatsuo; Suzuki, Toshiyuki; Hiruma, Minoru, Agricultural and Biological Chemistry, 1989, vol. 53, # 5, p. 1493 - 1502
  作者：Horiuchi, Tatsuo、Suzuki, Toshiyuki、Hiruma, Minoru、Saito, Narimasa

  DOI：——

  日期：——
• FERMENTATION PROCESS FOR PRODUCING MONOSACCHARIDES IN FREE FORM FROM NUCLEOTIDE-ACTIVATED SUGARS
  申请人：JENNEWEIN BIOTECHNOLOGIE GMBH

  公开号：US20180273996A1

  公开（公告）日：2018-09-27

  The present invention relates to a process for producing a monosaccharide, e.g. L-fucose, in free form using a microbial fermentation process. The used microorganism exhibits hydrolase activity on nucleotide-activated sugars and releases the monosaccharide in an unmodified free form. The free monosaccharide is retrieved from the supernatant of the cultivated microorganism.
• MODIFYING N-GLYCOSYLATION OF PLANT PROTEINS USING GDP-4-DEHYDRO-6-DEOXY-D-MANNOSE REDUCTASE (RMD)
  申请人：MEDICAGO INC.

  公开号：US20190225978A1

  公开（公告）日：2019-07-25

  A method for synthesizing a protein of interest with a modified N-glycosylation profile within a plant, a portion of a plant, or a plant cell is provided. The method comprises co-expressing within a plant a nucleotide sequence encoding a first nucleotide sequence encoding a GDP-4-dehydro-6-deoxy-D-mannose reductase (RMD) the first nucleotide sequence operatively linked with a first regulatory region that is active in the plant, and a second nucleotide sequence encoding the protein of interest, the second nucleotide sequence operatively linked with a second regulatory region that is active in the plant. The first and second nucleotide sequences are co-expressed to synthesize a protein of interest comprising glycans with the modified N-glycosylation profile within the plant, the portion of the plant, or the plant cell.