2'-azidoethyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside

• 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)-[α-L-fucopyranosyl-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: 2-azidoethyl-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonicacid)-(2→3)-b-D-galactopyranosyl-(1→4)[(1→3)-α-L-fucopyranosyl]-2-acetamido-2-deoxy-β-D-glucopyranoside；2-azidoethyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulo pyranosylonic acid)-(2->3)-β-D-galactopyranosyl-(1->4)[(1->3)-α-L-fucopyranosyl]-2-acetamido-2-deoxy-β-D-glucopyranoside；(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetamido-6-(2-azidoethoxy)-2-(hydroxymethyl)-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-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
• 化学式: C₃₃H₅₅N₅O₂₃
• 分子量: 889.819
• InChiKey: NJMBOLCJMVCBFX-DAIGYSRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  61
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  406
• 氢给体数：
  14
• 氢受体数：
  25

反应信息

• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 在 α-(1->3)-fucosyltransferase VI 、 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)-[α-L-fucopyranosyl-(1->3)]-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

• 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.
• WO2023/49265
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.