N-(acetyl)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine methylester | 196807-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(acetyl)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine methylester
• CAS: 196807-18-8
• 化学式: C₁₅H₂₆N₂O₉
• 分子量: 378.379
• InChiKey: GYTXJVSGOQOVIT-KOQXUCCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.99
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  163.65
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  cytidine-5'-monophosphono-N-acetylneuraminic acid 、 N-(acetyl)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine methylester 在 chST₆GalNAc I 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Efficient Chemoenzymatic Synthesis of O-Linked Sialyl Oligosaccharides

  摘要：

  The tumor associated Tn (GalNAcalpha(1-1)-Thr/Ser)- and T (Galbeta(1-3)-GalNAcalpha(1-1)Thr/Ser)antigens and their sialylated derivatives are present on the surface of many cancer cells. Preparative synthesis of these sialylated T- and Tn-structures has been achieved mainly from a chemical synthetic approach due to the lack of the required glycosyltransferases. We demonstrate a flexible and efficient chemoenzymatic approach for using recombinant sialyltransferases including a chicken GalNAcalpha2,6-sialyltransferase (chST6GalNAc1) and a porcine Galbeta(1-3)GalNAcalpha-2,3-sialyltransferase (pST3Gal 1). Using these enzymes, the common O-linked sialosides Neu5Acalpha(2-6)GalNAcalpha(1-1)Thr, Galbeta(1-3)[Neu5Acalpha(26)]GalNAcalpha(1-1)Thr, Neu5Acalpha(2-3)Galbeta(1-3)GalNAcalpha(1-1)Thr, and Neu5Acalpha(2-3)Galbeta(1-3)[Neu5Acalpha(-26)]GalNAcalpha(1-1)Thr were readily prepared at preparative scale. The chST6GalNAc I was found to require at least one amino acid (Thr/Ser) for optimal activity, and is thus an ideal catalyst for synthesis of synthetic glycopeptides and glycoconjugates with O-linked glycans.

  DOI：

  10.1021/ja017881+
• 作为产物：
  描述：

  sodium methylate 、 乙酸酐 、 N-(9-fluorenylmethyloxycarbonyl)-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester 以 甲醇 为溶剂， 反应 0.67h， 以47%的产率得到N-(acetyl)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine methylester
  参考文献：
  名称：

  Efficient Chemoenzymatic Synthesis of O-Linked Sialyl Oligosaccharides

  摘要：

  The tumor associated Tn (GalNAcalpha(1-1)-Thr/Ser)- and T (Galbeta(1-3)-GalNAcalpha(1-1)Thr/Ser)antigens and their sialylated derivatives are present on the surface of many cancer cells. Preparative synthesis of these sialylated T- and Tn-structures has been achieved mainly from a chemical synthetic approach due to the lack of the required glycosyltransferases. We demonstrate a flexible and efficient chemoenzymatic approach for using recombinant sialyltransferases including a chicken GalNAcalpha2,6-sialyltransferase (chST6GalNAc1) and a porcine Galbeta(1-3)GalNAcalpha-2,3-sialyltransferase (pST3Gal 1). Using these enzymes, the common O-linked sialosides Neu5Acalpha(2-6)GalNAcalpha(1-1)Thr, Galbeta(1-3)[Neu5Acalpha(26)]GalNAcalpha(1-1)Thr, Neu5Acalpha(2-3)Galbeta(1-3)GalNAcalpha(1-1)Thr, and Neu5Acalpha(2-3)Galbeta(1-3)[Neu5Acalpha(-26)]GalNAcalpha(1-1)Thr were readily prepared at preparative scale. The chST6GalNAc I was found to require at least one amino acid (Thr/Ser) for optimal activity, and is thus an ideal catalyst for synthesis of synthetic glycopeptides and glycoconjugates with O-linked glycans.

  DOI：

  10.1021/ja017881+