2-[(+)-biotinylamino]ethyl (L-glycero-α-D-manno-heptopyranosyl)-(1->2)-(L-glycero-α-D-manno-heptopyranosyl)-(1->3)-[(β-D-glucopyranosyl)-(1->4)]-L-glycero-α-D-manno-heptopyranoside | 1023637-30-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(+)-biotinylamino]ethyl (L-glycero-α-D-manno-heptopyranosyl)-(1->2)-(L-glycero-α-D-manno-heptopyranosyl)-(1->3)-[(β-D-glucopyranosyl)-(1->4)]-L-glycero-α-D-manno-heptopyranoside
• 英文别名: 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-[(2S,3S,4R,5R,6R)-6-[(1S)-1,2-dihydroxyethyl]-4-[(2R,3S,4S,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3-[(2R,3S,4S,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyethyl]pentanamide
• CAS: 1023637-30-0
• 化学式: C₃₉H₆₇N₃O₂₆S
• 分子量: 1026.03
• InChiKey: GHTPLQCHOWMCTL-FOFJDWHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.4
• 重原子数：
  69
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  493
• 氢给体数：
  19
• 氢受体数：
  27

反应信息

• 作为产物：
  描述：

  2-aminoethyl (L-glycero-α-D-manno-heptopyranosyl)-(1->2)-(L-glycero-α-D-manno-heptopyranosyl)-(1->3)-[(β-D-glucopyranosyl)-(1->4)]-L-glycero-α-D-manno-heptopyranoside 、 (+)生物素-N-琥珀酰亚胺基酯 在 三乙胺 作用下， 反应 0.5h， 生成 2-[(+)-biotinylamino]ethyl (L-glycero-α-D-manno-heptopyranosyl)-(1->2)-(L-glycero-α-D-manno-heptopyranosyl)-(1->3)-[(β-D-glucopyranosyl)-(1->4)]-L-glycero-α-D-manno-heptopyranoside
  参考文献：
  名称：

  Synthesis of a common tetrasaccharide motif of Haemophilus influenzae LPS inner core structures

  摘要：

  一种保守的四糖结构，L-glycero-α-D-manno-heptopyranosyl-(1→2)-(6-O-氨乙基膦酸-L-glycero-α-D-manno-heptopyranosyl)-(1→3)-[β-D-glucopyranosyl-(1→4)]-L-glycero-α-D-manno-heptopyranose，已从流感嗜血杆菌的LPS内核中合成为其乙基氨基糖苷，以便于后续的连接。从先前合成的适当保护的三糖中间体开始，引入了第三个七碳糖，随后通过硫糖苷供体化学引入了连接体。磷酸乙醇胺是通过使用Boc保护的磷酸酰胺化合物形成的。最后去保护并与生物素连接，得到的结合物将用于研究针对天然LPS结构的单克隆抗体的特异性。

  DOI：

  10.1039/b717564g

文献信息

• Synthesis of a common tetrasaccharide motif of Haemophilus influenzae LPS inner core structures
  作者：Karin Mannerstedt、Eva Segerstedt、Johan Olsson、Stefan Oscarson

  DOI：10.1039/b717564g

  日期：——

  A conserved tetrasaccharide structure, L-glycero-α-D-manno-heptopyranosyl-(1→2)-(6-O-aminoethylphosphono-L-glycero-α-D-manno-heptopyranosyl)-(1→3)-[β-D-glucopyranosyl-(1→4)]-L-glycero-α-D-manno-heptopyranose, from the LPS inner core of Haemophilus influenzae has been synthesised as its ethylamino glycosides to allow later conjugations. Starting from a previously synthesised suitably protected trisaccharide intermediate, the third heptose and subsequently the spacer were introduced using thioglycoside donor chemistry. The phosphoethanolamine was formed employing a Boc-protected phosphoamidite. Final deprotection and conjugation to biotin gave conjugates that will be used to study the specificity of MAbs raised against native LPS structures.

  一种保守的四糖结构，L-glycero-α-D-manno-heptopyranosyl-(1→2)-(6-O-氨乙基膦酸-L-glycero-α-D-manno-heptopyranosyl)-(1→3)-[β-D-glucopyranosyl-(1→4)]-L-glycero-α-D-manno-heptopyranose，已从流感嗜血杆菌的LPS内核中合成为其乙基氨基糖苷，以便于后续的连接。从先前合成的适当保护的三糖中间体开始，引入了第三个七碳糖，随后通过硫糖苷供体化学引入了连接体。磷酸乙醇胺是通过使用Boc保护的磷酸酰胺化合物形成的。最后去保护并与生物素连接，得到的结合物将用于研究针对天然LPS结构的单克隆抗体的特异性。