6-Methoxy-L-fucose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Methoxy-L-fucose
• 英文别名: O⁶-methyl-L-galactose；(3S,4R,5S,6S)-6-(methoxymethyl)oxane-2,3,4,5-tetrol
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: QWJKEQVWXSYDJA-DVEMRHSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-Methoxy-L-fucose 、 2'-azidoethyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside 在 manganese(II) sulfate 、 5’-三磷酸腺苷 、 Guanosine 5'-triphosphate 作用下， 以 aq. buffer 为溶剂， 反应 3.0h， 以95%的产率得到2-azidoethyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-β-D-galactopyranosyl-(1->4)[(1->3)-6-O-methyl-α-L-galactopyranosyl]-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of the sialyl Lewis X glycan and its derivatives

  摘要：

  A combination of recombinant FKP and alpha-(1 -> 3)-fucosyltransferase allows the facile synthesis of the sialyl Lewis X tetrasaccharide glycan and its derivatives in excellent yield. In this system, the universal fucosyl donor, guanidine 5'-diphosphate-beta-L-fucose (GDP-fucose), or its analogues can be generated in situ by cofactor recycling using pyruvate kinase. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.03.032
• 作为产物：
  描述：

  1-羟基-3-(磷酰氧基)-2-丙酮 、 2-hydroxy-3-methoxypropionaldehyde 生成 6-Methoxy-L-fucose
  参考文献：
  名称：

  Enzymic Synthesis of L-Fucose and Analogs

  摘要：

  DOI：

  10.1021/jo00127a052

文献信息

• Enzymic Synthesis of L-Fucose and Analogs
  作者：Chi-Huey Wong、Ramon Alajarin、Francisco Moris-Varas、Olga Blanco、Eduardo Garcia-Junceda

  DOI：10.1021/jo00127a052

  日期：1995.11
• Chemoenzymatic synthesis of the sialyl Lewis X glycan and its derivatives
  作者：David Soriano del Amo、Wei Wang、Christen Besanceney、Tianqing Zheng、Yizheng He、Brian Gerwe、Ronald D. Seidel、Peng Wu

  DOI：10.1016/j.carres.2010.03.032

  日期：2010.6

  A combination of recombinant FKP and alpha-(1 -> 3)-fucosyltransferase allows the facile synthesis of the sialyl Lewis X tetrasaccharide glycan and its derivatives in excellent yield. In this system, the universal fucosyl donor, guanidine 5'-diphosphate-beta-L-fucose (GDP-fucose), or its analogues can be generated in situ by cofactor recycling using pyruvate kinase. (C) 2010 Elsevier Ltd. All rights reserved.