Boc-Thr(α-GalNAc)-OH | 1271737-90-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Boc-Thr(α-GalNAc)-OH
• 英文别名: N^α-(tert-butoxycarbonyl)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine；O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-threonine
• CAS: 1271737-90-6
• 化学式: C₁₇H₃₀N₂O₁₀
• 分子量: 422.433
• InChiKey: IGYFCVZETFKLHI-HOIITPSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.69
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  183.88
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Boc-Thr(α-GalNAc)-OH 以3.6%的产率得到2-(acetylamino)-2-deoxy-α-D-galactopyranosyl-L-threonine
  参考文献：
  名称：

  Condensation reactions catalyzed by α-N-acetylgalactosaminidase fromAspergillus nigeryielding α-N-acetylgalactosaminides

  摘要：

  Extracellular alpha-N-acetylgalactosaminidase from Aspergillus niger catalyzed glycosylation yielding a series of 2-acetamido-2-deoxy-alpha-D-galactobiosides using 2-acetamido-2-deoxy-D-galactopyranose as a glycosyl donor. The isomers alpha-D-GalpNAc-(1 -> 6)-D-GalpNAc, alpha-D-GalpNAc-(1 -> 3)-D-GalpNAc and alpha-D-GalpNAc-(1 -> 6)-D-GalfNAc were isolated and spectrally characterized. The purified enzyme was further used for the glycosylation of free amino acids (serine and threonine) and their N-(tert-butoxycarbonyl)-protected analogs to synthesize the Tn antigen (GalpNAc-alpha-O-Ser/Thr) and its N-(tert-butoxycarbonyl)-protected derivatives.

  DOI：

  10.3109/10242421003587227
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-D-吡喃半乳糖 、 Boc-L-苏氨酸 在 α-N-acetylgalactosaminidase from Aspergillus niger CCIM K2 作用下， 反应 240.0h， 生成 Boc-Thr(α-GalNAc)-OH
  参考文献：
  名称：

  Condensation reactions catalyzed by α-N-acetylgalactosaminidase fromAspergillus nigeryielding α-N-acetylgalactosaminides

  摘要：

  Extracellular alpha-N-acetylgalactosaminidase from Aspergillus niger catalyzed glycosylation yielding a series of 2-acetamido-2-deoxy-alpha-D-galactobiosides using 2-acetamido-2-deoxy-D-galactopyranose as a glycosyl donor. The isomers alpha-D-GalpNAc-(1 -> 6)-D-GalpNAc, alpha-D-GalpNAc-(1 -> 3)-D-GalpNAc and alpha-D-GalpNAc-(1 -> 6)-D-GalfNAc were isolated and spectrally characterized. The purified enzyme was further used for the glycosylation of free amino acids (serine and threonine) and their N-(tert-butoxycarbonyl)-protected analogs to synthesize the Tn antigen (GalpNAc-alpha-O-Ser/Thr) and its N-(tert-butoxycarbonyl)-protected derivatives.

  DOI：

  10.3109/10242421003587227

文献信息

• Total Synthesis of<i>O</i>-GalNAcylated Antifreeze Glycoprotein using the Switchable Reactivity of Peptidyl-<i>N</i>-pivaloylguanidine
  作者：Ryo Orii、Noriko Sakamoto、Daichi Fukami、Sakae Tsuda、Masayuki Izumi、Yasuhiro Kajihara、Ryo Okamoto

  DOI：10.1002/chem.201702243

  日期：2017.7.12

  between structure and activity of O‐GalNAcylated AFGP using homogeneous glycoproteins. Thus, the total synthesis of homogeneous O‐GalNAcylated AFGP was conducted by using a unique peptide derivative: peptidyl‐N‐pivaloylguanidine. It was found that peptidyl‐N‐pivaloylguanidine is an “unreactive” peptide in peptide coupling reactions but is interconvertible with a “reactive” peptide‐α‐thioester by means

  抗冻糖蛋白（AFGP）是一种O糖蛋白，可通过降低水的凝固点来显示抗冻活性。GalNAc是AFGP的核心糖结构，并有助于诱导该糖蛋白的抗冻活性。但是，这种糖在分子水平上所起的一般功能作用仍是未知的。为了阐明这一点，必须使用均一的糖蛋白确定O- GalNAcylated AFGP的结构与活性之间的关系。因此，均质O- GalNAcylated AFGP的总合成是通过使用独特的肽衍生物：肽基-N-新戊酰胍。发现肽基N-pivaloylguanidine是一个“不反应的”肽在肽偶联反应，但是可以相互转换与“反应性”肽- α -硫酯通过缓冲液条件下在pH = 7〜8的肽基的独特反应性可切换的简单处理来ñ -新戊酰胍使高效的顺序肽偶联策略成为可能。通过使用这种策略，合成了各种长度的均一的O- GalNAcylated AFGP，包括长度为120个氨基酸的40个O- GalNAcylation位点。圆二
• Regulating Antifreeze Activity through Water: Latent Functions of the Sugars of Antifreeze Glycoprotein Revealed by Total Chemical Synthesis
  作者：Ryo Okamoto、Ryo Orii、Hiroyuki Shibata、Yuta Maki、Sakae Tsuda、Yasuhiro Kajihara

  DOI：10.1002/chem.202203553

  日期：——

  The total chemical synthesis of antifreeze glycoprotein (AFGP) derivatives including partially sugar deleted forms and unnatural forms incorporating glucose-type sugars instead of galactose-type sugars of the natural form is described. These elaborated AFGPs indicate a unique function of the sugar residues that form a unique dynamic water phase, thereby inhibiting freezing.

  描述了抗冻糖蛋白 (AFGP) 衍生物的全化学合成，包括部分糖缺失形式和包含葡萄糖型糖而不是天然形式的半乳糖型糖的非天然形式。这些精心制作的 AFGP 表明糖残基具有独特的功能，可形成独特的动态水相，从而抑制冻结。