2-deoxyglucose-6-phosphate | 27638-67-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxyglucose-6-phosphate
• 英文别名: 2-Deoxy-6-O-Phosphono-Alpha-D-Arabino-Hexopyranose；[(2R,3S,4R,6S)-3,4,6-trihydroxyoxan-2-yl]methyl dihydrogen phosphate
• CAS: 27638-67-1
• 化学式: C₆H₁₃O₈P
• 分子量: 244.138
• InChiKey: UQJFZAAGZAYVKZ-ZXXMMSQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-deoxyglucose-6-phosphate 、 胸苷酸 在 D-葡糖-1,6-二磷酸 、 乙酰磷酸 、 recombinant acetate kinase from Escherichia coli K₁₂ 、 recombinant phosphomannomutase from Escherichia coli K₁₂ 、 recombinant TDP-glucose synthase from Escherichia coli K₁₂ 、 recombinant TMP kinase from Escherichia coli K₁₂ 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 反应 3.0h， 生成 thymidine 5'-(2-deoxy-α-D-glucopyranosyl diphosphate)
  参考文献：
  名称：

  One-pot enzymatic synthesis of deoxy-thymidine-diphosphate (TDP)-2-deoxy-α-d-glucose using phosphomannomutase

  摘要：

  Production of deoxy-thymidine-diphosphate (TDP)-sugars as Substrates of glycosyltransferases, has been one of main hurdles for combinatorial antibiotic biosynthesis, which combines sugar moiety with aglycon of various antibiotics. Here, we report the one-pot enzymatic synthesis of TDP-2-deoxy-glucose employing high efficient TMP kinase (TMK; E.C. 2.7.2.12), acetate kinase (ACK; E.C. 2.7.1.21), and TDP-glucose synthase (TGS; E.C. 2.7.7.24) with phosphomannomutase (PMM; E.C. 5.4.2.8). In this study, replacing phosphoglucomutase (PGM; E.C. 5.4.2) by PMM from Escherichia coli gave four times higher specific activity on 2-deoxy-6-phosphate glucose, suggesting that the activity on 2-deoxy-glucose-6-phosphate was mainly affected by PMM activity. not PGM activity. Using an in vitro system starting from TMP and 2-deoxy-glucose-6-phosphate glucose, TDP-2-deoxy-glucose (63% yield) was successfully synthesized. Considering low productivity of NDP-sugars from cheap starting materials, this paper showed how production of NDP-sugars Could be enhanced by controlling mutase activity. (C) 2009 Published by Elsevier B.V.

  DOI：

  10.1016/j.molcatb.2009.11.008

文献信息

• One-pot enzymatic synthesis of deoxy-thymidine-diphosphate (TDP)-2-deoxy-α-d-glucose using phosphomannomutase
  作者：Yung-Hun Yang、Young-Bok Kang、Dae-Hee Kim、Tek-Hyung Lee、Sung-Hee Park、Kwangwon Lee、Dongwon Yoo、Kwang-kyung Liou、Hee-Chan Lee、Jae-Kyung Sohng、Byung-Gee Kim

  DOI：10.1016/j.molcatb.2009.11.008

  日期：2010.3

  Production of deoxy-thymidine-diphosphate (TDP)-sugars as Substrates of glycosyltransferases, has been one of main hurdles for combinatorial antibiotic biosynthesis, which combines sugar moiety with aglycon of various antibiotics. Here, we report the one-pot enzymatic synthesis of TDP-2-deoxy-glucose employing high efficient TMP kinase (TMK; E.C. 2.7.2.12), acetate kinase (ACK; E.C. 2.7.1.21), and TDP-glucose synthase (TGS; E.C. 2.7.7.24) with phosphomannomutase (PMM; E.C. 5.4.2.8). In this study, replacing phosphoglucomutase (PGM; E.C. 5.4.2) by PMM from Escherichia coli gave four times higher specific activity on 2-deoxy-6-phosphate glucose, suggesting that the activity on 2-deoxy-glucose-6-phosphate was mainly affected by PMM activity. not PGM activity. Using an in vitro system starting from TMP and 2-deoxy-glucose-6-phosphate glucose, TDP-2-deoxy-glucose (63% yield) was successfully synthesized. Considering low productivity of NDP-sugars from cheap starting materials, this paper showed how production of NDP-sugars Could be enhanced by controlling mutase activity. (C) 2009 Published by Elsevier B.V.