(2R,4S,5R,6R)-5-Acetylamino-2-((2R,3R,4R,5R,6R)-5-acetylamino-3,4,6-trihydroxy-tetrahydro-pyran-2-ylmethoxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5R,6R)-5-Acetylamino-2-((2R,3R,4R,5R,6R)-5-acetylamino-3,4,6-trihydroxy-tetrahydro-pyran-2-ylmethoxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid
• 英文别名: NeuAc(a2-6)b-GalNAc；(2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4R,5R,6R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• 化学式: C₁₉H₃₂N₂O₁₄
• 分子量: 512.468
• InChiKey: CZOGCRVBCLRHQJ-XBVKUWPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  265
• 氢给体数：
  10
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-D-吡喃半乳糖 、 N-乙酰神经氨酸水合物 在 果糖 、 Corynebacterium ammoniagenes 、 potassium orotate 作用下， 以 xylene 为溶剂， 生成 Neu5Acα2->6GalNAcα 、 (2R,4S,5R,6R)-5-Acetylamino-2-((2R,3R,4R,5R,6R)-5-acetylamino-3,4,6-trihydroxy-tetrahydro-pyran-2-ylmethoxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Large-scale production of the carbohydrate portion of the sialyl–Tn epitope, α-Neup5Ac-(2→6)-d-GalpNAc, through bacterial coupling

  摘要：

  alpha -Neup5Ac-(2 --> 6)-D-GalpNAc, the carbohydrate portion of sialyl-Tn epitope of the tumor-associated carbohydrate antigen, was prepared by a whole-cell reaction through the combination of recombinant Escherichia coli strains and Corynebacterium ammoniagenes. Two recombinant E. coli strains overexpressed the CMP-Neup 5Ac biosynthetic genes and the alpha-(2 --> 6)-sialyltransferase gene of Photobacterium damsela. C. ammoniagenes contributed to the production of UTP from orotic acid. alpha -NeupSAc-(2 --> 6)-D-GalpNAc was accumulated at 87 mM (45 g/L) after a 25-h reaction starting from orotic acid, N-acetylneuraminic acid, and 2-acetamide-2-deoxy-D-galactose. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00007-6

文献信息

• Large-scale production of the carbohydrate portion of the sialyl–Tn epitope, α-Neup5Ac-(2→6)-d-GalpNAc, through bacterial coupling
  作者：Tetsuo Endo、Satoshi Koizumi、Kazuhiko Tabata、Shingo Kakita、Akio Ozaki

  DOI：10.1016/s0008-6215(01)00007-6

  日期：2001.2

  alpha -Neup5Ac-(2 --> 6)-D-GalpNAc, the carbohydrate portion of sialyl-Tn epitope of the tumor-associated carbohydrate antigen, was prepared by a whole-cell reaction through the combination of recombinant Escherichia coli strains and Corynebacterium ammoniagenes. Two recombinant E. coli strains overexpressed the CMP-Neup 5Ac biosynthetic genes and the alpha-(2 --> 6)-sialyltransferase gene of Photobacterium damsela. C. ammoniagenes contributed to the production of UTP from orotic acid. alpha -NeupSAc-(2 --> 6)-D-GalpNAc was accumulated at 87 mM (45 g/L) after a 25-h reaction starting from orotic acid, N-acetylneuraminic acid, and 2-acetamide-2-deoxy-D-galactose. (C) 2001 Elsevier Science Ltd. All rights reserved.