5-azido-3-oxapentyl 2-acetamido-2-deoxy-α-D-galactopyranoside | 195531-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-3-oxapentyl 2-acetamido-2-deoxy-α-D-galactopyranoside
• 英文别名: N-[(2S,3R,4R,5R,6R)-2-[2-(2-azidoethoxy)ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 195531-55-6
• 化学式: C₁₂H₂₂N₄O₇
• 分子量: 334.329
• InChiKey: YIYBKMXLQSWSPH-ZIQFBCGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-azido-3-oxapentyl 2-acetamido-2-deoxy-α-D-galactopyranoside 在 bovine β-galactosidase 、 pork liver α-(2->3) sialyltransferase 作用下， 以 phosphate buffer 为溶剂， 反应 84.0h， 生成 5-azido-3-oxapentyl 3-O-{(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonate)-3-O-(β-D-galactopyranosyl)}-2-acetamido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of spacer-linked oligosaccharides for the preparation of neoglycoproteins

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(99)00073-7
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-D-吡喃半乳糖 在 sodium azide 、 四丁基碘化铵 、 乙酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-azido-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

• 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。
• Galactosylation with β-galactosidase from bovine testes employing modified acceptor substrates
  作者：Ulrike Gambert、Raul Gonzalez Lio、Erzsébet Farkas、Joachim Thiem、Vicente Verez Bencomo、András Lipták

  DOI：10.1016/s0968-0896(97)00071-0

  日期：1997.7

  In this study beta 1-3 linked analogues of the T-antigen determinant were sythesized in preparative scale by transgalactosylation using beta-galactosidase from bovine testes to give synthetic antigens. Accepters with modifications of the sugar residue such as alpha-glycosylated spacers, as well as GlcNAc-alpha OR- and 2dGal-alpha OR-substrates opened further possibilities for galactosylation. (C) 1997 Elsevier Science Ltd.
• 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.
• 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.