5-amino-3-oxapentyl 2-acetamido-2-deoxy-α-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-amino-3-oxapentyl 2-acetamido-2-deoxy-α-D-galactopyranoside
• 英文别名: 2'-(2''-aminoethoxy)ethyl-2-acetamido-2-deoxygalactopyranoside；N-[(2S,3R,4R,5R,6R)-2-[2-(2-aminoethoxy)ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₁₂H₂₄N₂O₇
• 分子量: 308.332
• InChiKey: CQAOFARJZQYFML-ZIQFBCGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  144
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  adipic acid bis(pentafluorophenyl)ester 、 5-amino-3-oxapentyl 2-acetamido-2-deoxy-α-D-galactopyranoside 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以47%的产率得到
  参考文献：
  名称：

  用于蛋白质缀合的多氟苯基酯封端的同型双功能交联剂

  摘要：

  与 N-羟基琥珀酰亚胺、对硝基苯基和苯基硒代酯一起，在反应性和水解稳定性方面对四氟和五氟苯基酯进行了比较评估。他们制备了同型双功能交联剂以将蛋白质与小分子结合，包括碳水化合物、荧光染料和聚（乙二醇）单甲醚。偶联在温和条件下进行，以良好的效率提供相应的蛋白质偶联物。

  DOI：

  10.1055/s-0036-1590974
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-D-吡喃半乳糖 在 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 四丁基碘化铵 、 乙酰氯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-amino-3-oxapentyl 2-acetamido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Preparation of Protein Conjugates via Homobifunctional Diselenoester Cross-Linker

  摘要：

  Adipic acid diselenoester was developed as an efficient cross-linker for covalent protein conjugation with a variety of small molecular haptens, including mono- and disaccharides, peptide, fluorescence dye, and nicotine. Compared to the counterparts of N-hydroxysuccinimide (NHS) and p-nitrophenyl (PNP) linkers, the diselenoester linker demonstrates improved balance between reactivity and stability and coupling of haptens to proteins under mild conditions with high incorporation efficiency.

  DOI：

  10.1021/acs.orglett.6b02568

文献信息

• Green glycosylation using ionic liquid to prepare alkyl glycosides for studying carbohydrate–protein interactions by SPR
  作者：F. Javier Muñoz、Sabine André、Hans-Joachin Gabius、José V. Sinisterra、María J. Hernáiz、Robert J. Linhardt

  DOI：10.1039/b814171a

  日期：——

  Several simple glycosides of D-glucose (Glc) and N-acetyl-D-galactosamine (GalNAc) were prepared in a single step glycosylation reaction using unprotected and unactivated sugar donors. The resulting GalNAc glycoside, containing a bifunctional linker, was used to immobilize this glycoconjugate to a self assembled monolayer on a gold biosensor chip. Surface plasmon resonance (SPR) experiments demonstrated that this immobilized glycoconjugate bound to GalNAc specific lectin, Viscum album agglutinin.

  通过使用未保护和未活化的糖供体，在一步糖基化反应中制备了几种简单的D-葡萄糖（Glc）和N-乙酰-D-半乳糖胺（GalNAc）的糖苷。得到的含有双功能连接子的GalNAc糖苷，被用来将这种糖缀合物固定在黄金生物传感器芯片上的自组装单层上。表面等离子体共振（SPR）实验证明，这种固定的糖缀合物能够与GalNAc特异性凝集素，即槲寄生凝集素结合。
• Chemoenzymatic synthesis of spacer-linked oligosaccharides for the preparation of neoglycoproteins
  作者：Raul Gonzalez Lio、Joachim Thiem

  DOI：10.1016/s0008-6215(99)00073-7

  日期：1999.4

  In the present work, the combination of chemical and enzymatic methods to obtain neoglycoproteins is described. Three bovine serum albumin (BSA)-conjugates, BSA-[GalNAc alpha-], BSA-[Gal(beta 1-3)GalNAc(alpha-], and BSA-[Neu5Ac(alpha 2-3)Gal(beta 1-3)GalNAc(alpha-], were prepared, alpha GalNAc derivatives were galactosylated employing crude P-galactosidase from bovine testes. The use of oversaturated donor solutions (pNP beta Gal) enhanced the yields up to 60%. This method was verified using divalent structures as accepters, that rendered di- and tri-galactosylated products. Further treatment of the disaccharides with CMP-Neu5Ac and alpha 2-3 sialyltransferase from pork liver led to formation of trisaccharides. Finally, mono-, di-, and trisaccharides were coupled to BSA employing a thiolic group introduced into the protein for Michael addition to a maleinimide group in the spacer-ann of the saccharide components. The results were monitored by HPLC and MALDI-TOF. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Preparation of Protein Conjugates via Homobifunctional Diselenoester Cross-Linker
  作者：Xu-Guang Yin、Xiao-Fei Gao、Jing-Jing Du、Xiao-Kang Zhang、Xiang-Zhao Chen、Jian Wang、Ling-Ming Xin、Ze Lei、Zheng Liu、Jun Guo

  DOI：10.1021/acs.orglett.6b02568

  日期：2016.11.18

  Adipic acid diselenoester was developed as an efficient cross-linker for covalent protein conjugation with a variety of small molecular haptens, including mono- and disaccharides, peptide, fluorescence dye, and nicotine. Compared to the counterparts of N-hydroxysuccinimide (NHS) and p-nitrophenyl (PNP) linkers, the diselenoester linker demonstrates improved balance between reactivity and stability and coupling of haptens to proteins under mild conditions with high incorporation efficiency.
• Polyfluorophenyl Ester-Terminated Homobifunctional Cross-Linkers for Protein Conjugation
  作者：Zheng Liu、Jun Guo、Jian Wang、Ru-Yan Zhang、Ya-Cong Wang、Xiang-Zhao Chen、Xu-Guang Yin、Jing-Jing Du、Ze Lei、Ling-Ming Xin、Xiao-Fei Gao

  DOI：10.1055/s-0036-1590974

  日期：2017.9

  reactivity and hydrolytic stability. Their homobifunctional cross-linkers were prepared to conjugate proteins with small molecules, including carbohydrates, fluorescent dyes, and poly(ethylene glycol) monomethyl ether. The conjugations proceeded under mild conditions, affording the corresponding protein conjugates with good efficiency.

  与 N-羟基琥珀酰亚胺、对硝基苯基和苯基硒代酯一起，在反应性和水解稳定性方面对四氟和五氟苯基酯进行了比较评估。他们制备了同型双功能交联剂以将蛋白质与小分子结合，包括碳水化合物、荧光染料和聚（乙二醇）单甲醚。偶联在温和条件下进行，以良好的效率提供相应的蛋白质偶联物。