2'-azidoethyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside | 485388-17-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-azidoethyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: 2-azidoethyl sLacNAc；(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetamido-6-(2-azidoethoxy)-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 485388-17-8
• 化学式: C₂₇H₄₅N₅O₁₉
• 分子量: 743.676
• InChiKey: XLVPCEAYZMPSBT-BJHNEYRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  347
• 氢给体数：
  12
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  L-galactose 、 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80%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)-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：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 在 β-(1->4)-galactosyltransferase 、 ST₃Gal-CMP-Neup₅Ac fusion protein 、 UDP-galactose 4'-epimerase 、 sodium cacodylate 、 manganese(ll) chloride 作用下， 以 水 为溶剂， 反应 42.0h， 生成 2'-azidoethyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Large-scale chemoenzymatic synthesis of blood group and tumor-associated poly-N-acetyllactosamine antigens

  摘要：

  Poly-N-acetyllactosamines (pLNs) are common terminal sugars of many N- and O-linked glycan structures present in glycoproteins and glycolipids. Utilizing various glycosyltransferases, we developed new and efficient chemoenzymatic methods for the synthesis of pLNs in gram-scale. Specifically, the use of sialyltransferases and fucosyltransferases enabled us to synthesize and purify 24 blood group and tumor-associated pLN derivatives with alpha-(2 -> 3)- and alpha-(2 -> 6)-linked sialic acid, as well as with alpha-(1 -> 2)- and alpha-(1 -> 3)-linked fucose. All synthesized derivatives were linked to a short 2-azidoethyl spacer for further modification. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.043

文献信息

• Large-scale chemoenzymatic synthesis of blood group and tumor-associated poly-N-acetyllactosamine antigens
  作者：Daniela Vasiliu、Nahid Razi、Yingning Zhang、Nathan Jacobsen、Kirk Allin、Xiaofei Liu、Julia Hoffmann、Ognian Bohorov、Ola Blixt

  DOI：10.1016/j.carres.2006.03.043

  日期：2006.7

  Poly-N-acetyllactosamines (pLNs) are common terminal sugars of many N- and O-linked glycan structures present in glycoproteins and glycolipids. Utilizing various glycosyltransferases, we developed new and efficient chemoenzymatic methods for the synthesis of pLNs in gram-scale. Specifically, the use of sialyltransferases and fucosyltransferases enabled us to synthesize and purify 24 blood group and tumor-associated pLN derivatives with alpha-(2 -> 3)- and alpha-(2 -> 6)-linked sialic acid, as well as with alpha-(1 -> 2)- and alpha-(1 -> 3)-linked fucose. All synthesized derivatives were linked to a short 2-azidoethyl spacer for further modification. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.