O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-hydroxysuccinimide | 215037-76-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-hydroxysuccinimide
• 英文别名: 2-azido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl hydroxysuccinimide
• CAS: 215037-76-6
• 化学式: C₁₆H₂₀N₄O₁₀
• 分子量: 428.356
• InChiKey: ZCJIDSILDMATNS-LMXXTMHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  183.5
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-hydroxysuccinimide 在 palladium on activated charcoal 氢气 作用下， 以 水 为溶剂， 生成 GalNAc-α-ONH2
  参考文献：
  名称：

  包含与肿瘤相关的T（N）和唾液酸T（N）抗原的肟连接的粘蛋白模拟物的合成。

  摘要：

  [反应-见正文]肟连接的粘蛋白模拟物的合成是通过将多个酮残基掺入肽中，然后与对应于肿瘤相关T（N）和唾液酸T（N）的氨氧基糖反应完成的（ ST（N））抗原。

  DOI：

  10.1021/ol0166247
• 作为产物：
  描述：

  2-叠氮-D-半乳糖四乙酸酯 在 四丁基硫酸氢铵 、 四氯化钛 、 sodium carbonate 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-hydroxysuccinimide
  参考文献：
  名称：

  Immunological Response from an Entirely Carbohydrate Antigen: Design of Synthetic Vaccines Based on Tn−PS A1 Conjugates

  摘要：

  An entirely carbohydrate-based immunogen consisting of a zwitterionic polysaccharide (ZPS) PS A1 and the well-known tumor antigen Tn has been designed, synthesized, and studied for immunological effects. The PS A1 motif was included to act as an MHCII elicitor for a T-cell-dependent immune response with increased immunogenicity against tumor-associated carbohydrate antigens, providing an alternative to carrier proteins. Through the use of C57BL/6 mice, it has been shown that chemical modification of PS A1 does not alter the recognition sequence responsible for an MHCII-mediated, T-cell-dependent immune response. The Tn-PS A1 conjugate construct confers specificity toward the Tn antigen alone, and specific carbohydrate immunoglobulins, namely, IgG3, are generated from intraperitoneal immunizations with or without adjuvant. The properties of the vaccine candidate are attributed to a site-specific linking strategy that incurs significant incorporation of Tn antigen.

  DOI：

  10.1021/ja902607a

文献信息

• Synthesis of an oxime-linked neoglycopeptide with glycosylation-dependent activity similar to its native counterpart
  作者：Lisa A. Marcaurelle、Elena C. Rodriguez、Carolyn R. Bertozzi

  DOI：10.1016/s0040-4039(98)01831-0

  日期：1998.11

  Neoglycopeptides containing an oxime sugar-peptide linkage can be generated by coupling an aminooxy sugar with a peptide bearing a keto-amino acid. The coupling reaction can be executed in aqueous milieu without need for protecting groups on the peptide or saccharide, or auxiliary coupling reagents. Using this method, an oxime-linked analog of an antimicrobial peptide with glycosylation-dependent function

  含有肟糖-肽键的新糖肽可以通过将氨氧基糖与带有酮-氨基酸的肽偶联而产生。偶联反应可以在水溶液中进行，而无需保护肽或糖或辅助偶联剂上的基团。使用该方法，制备了具有糖基化依赖性功能的抗微生物肽的肟连接类似物，并发现其具有与天然糖肽相似的生物活性。因此，用非天然但合成上容易的键取代糖-肽键可产生功能性新糖肽。
• Elucidating structural features of an entirely carbohydrate cancer vaccine construct employing circular dichroism and fluorescent labeling
  作者：Kevin R. Trabbic、Ravindra A. De Silva、Peter R. Andreana

  DOI：10.1039/c4md00038b

  日期：——

  carbohydrate cancer antigen, the Thomsen-nouveau (Tn = alpha-D-GalNAc-OSer/Thr) antigen, does not alter antibody isotype switching ability and leads to specific IgG3 antibodies in C57BL/6 mice. Circular dichroism (CD) and studies using fluorescently labeled PS A1, described herein, reveal information pertaining to structure–activity relationships and the nature of Tn conjugation to chemically modified PS A1

  已知来自脆弱厌氧杆菌的两性离子多糖PS A1 ATCC 25285 / NCTC 9343会诱导T细胞依赖性，主要的组织相容性复合体II类（MHCII）免疫反应，通过相应的类似的基于蛋白质抗原的机制/途径进行。已知PS A1的生物学活性是由相邻单糖上的交替带电基序产生的，所述单糖包含四聚体重复寡聚单元，形成α-螺旋二级结构。但是，我们已经知道，这种α-螺旋结构特征可能不会在免疫激活中起作用。矛盾的是，我们目前对带静电多糖的结构-活性关系（SAR）的了解已变得更加清晰，但是缺乏用于测量动态结构变化的工具/探针，阻碍了基于碳水化合物的疫苗开发的进展。PS A1的针对特定地点和特定区域的结构修改，d-GalNAc-OSer / Thr）抗原，不会改变抗体同种型转换能力，并导致C57BL / 6小鼠产生特异性IgG3抗体。本文描述的圆二色性（CD）和使用荧光标记的PS A1的研究揭示了有关结构-活性关系以及Tn与化学修饰的PS
• Aminooxy-, Hydrazide-, and Thiosemicarbazide-Functionalized Saccharides:  Versatile Reagents for Glycoconjugate Synthesis
  作者：Elena C. Rodriguez、Lisa A. Marcaurelle、Carolyn R. Bertozzi

  DOI：10.1021/jo981351n

  日期：1998.10.1
• <i>N</i>-(2-Acetamido-3,4,6-tri-<i>O</i>-acetyl-2-deoxy-α-<scp>D</scp>-galactopyranosyloxy)succinimide
  作者：Olivier Renaudet、Pascal Dumy、Christian Philouze、Marie-Thérèse Averbuch-Pouchot

  DOI：10.1107/s0108270101003377

  日期：2001.5.15

  The crystal structure of the title compound, C18H24N2O11, a GalNAc mimic containing an alpha -glycosyloxysuccinimide linkage, has been determined. The pyranose ring geometry is an almost perfect C-4(1) chair. The torsion angle of the exocyclic hydroxymethyl group is shown to be gauche-trans with respect to O1 and C4, respectively.