N-((2S,3R,4R,5R,6R)-2-(((2R,3R,4S,5S,6R)-2-(((2R,3R,4R,5R,6S)-6-(((2R,3S,4R,5R,6R)-6-(allyloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-4-(((2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2Hpyran-2-yl)oxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((2S,3R,4R,5R,6R)-2-(((2R,3R,4S,5S,6R)-2-(((2R,3R,4R,5R,6S)-6-(((2R,3S,4R,5R,6R)-6-(allyloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-4-(((2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2Hpyran-2-yl)oxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide
• 英文别名: allyl-fucosyl-Gb5；allyl-Globo H；Fuc(a1-2)Gal(b1-3)GalNAc(b1-3)Gal(a1-4)Gal(b1-4)Glc(b)-O-allyl；N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-prop-2-enoxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₄₁H₆₉NO₃₀
• 分子量: 1055.99
• InChiKey: PMRBHFFDSNTVLN-FGBRNMJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10
• 重原子数：
  72
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  484
• 氢给体数：
  18
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  N-((2S,3R,4R,5R,6R)-2-(((2R,3R,4S,5S,6R)-2-(((2R,3R,4R,5R,6S)-6-(((2R,3S,4R,5R,6R)-6-(allyloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-4-(((2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2Hpyran-2-yl)oxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide 在 二甲基硫 、 臭氧 作用下， 生成
  参考文献：
  名称：

  Immunization of Mice with a Fully Synthetic Globo H Antigen Results in Antibodies against Human Cancer Cells: A Combined Chemical—Immunological Approach to the Fashioning of an Anticancer Vaccine

  摘要：

  DOI：

  10.1002/anie.199701251
• 作为产物：
  描述：

  (2S,3R,4S,5R,6R)-2-(((2R,3S,4R,5R,6R)-6-(allyloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 在 2(1H)-喹啉酮,1-丙基- 、 pyrophosphatase 、 pyruvate kinase 、 N-acetylhexosamine 1-kinase 、 α-1,2-fucosyltransferase 、 α-1,4-galactosyltransferase 、 β-1,3-galactosyltransferase 、 β-1,3-N-acetylgalactosaminyltransferase 、 L-fucokinase/GDP-fucose pyrophosphorylase 、 N-acetylglucosamine 1-phosphate uridylyltransferase 、 UDP-sugar pyrophosphorylase 、 phosphoenolpyruvic acid monopotassium salt 、 尿苷-5'-三磷酸 、 5’-三磷酸腺苷 、 Guanosine 5'-triphosphate 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 480.0h， 生成 N-((2S,3R,4R,5R,6R)-2-(((2R,3R,4S,5S,6R)-2-(((2R,3R,4R,5R,6S)-6-(((2R,3S,4R,5R,6R)-6-(allyloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-4-(((2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2Hpyran-2-yl)oxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide
  参考文献：
  名称：

  用于 Globo H 和 SSEA4 大规模酶法合成的有效糖核苷酸再生

  摘要：

  我们在此报告了通过使用过表达的糖基转移酶和糖核苷酸的有效再生，大规模合成癌症相关抗原 globpentaose (Gb5)、岩藻糖基-Gb5 (Globo H) 和唾液酸-Gb5 (SSEA4) 的化学酶学方法的发展，包括 UDP-Gal、UDP-GalNAc、GDP-Fuc 和 CMP-Neu5Ac。合成中使用的酶首先通过比较研究从不同物种中鉴定出来，然后在大肠杆菌中过表达并分离用于合成。这些方法只需两到三个纯化步骤即可高产地提供数克数量的产品，适用于癌症疫苗和疗法的评估和开发。

  DOI：

  10.1021/ja4075584

文献信息

• Total Synthesis and Proof of Structure of a Human Breast Tumor (Globo-H) Antigen
  作者：Tae Kyo Park、In Jong Kim、Shuanghua Hu、Mark T. Bilodeau、John T. Randolph、Ohyun Kwon、Samuel J. Danishefsky

  DOI：10.1021/ja962048b

  日期：1996.1.1

  The total synthesis of the Hakomori MBr1 antigen, heavily expressed on human breast tumors, is related. The construction involved the assembly of four glycals: (17 (twice), 18, 20, and 26) and an l-fucose derivative, 34. The sensitivity of the stereochemistry of sulfonamido galactosylation by a terminal galactose ring as a function of the state of protection status of its C4 alcohol was exploited in

  Hakomori MBr1 抗原的全合成，在人类乳腺肿瘤上大量表达，是相关的。该构建涉及四种糖基的组装：（17（两次）、18、20 和 26）和 l-岩藻糖衍生物，34。作为状态函数的末端半乳糖环磺酰氨基半乳糖基化立体化学的敏感性在关键步骤中利用其C4醇的保护状态。（参见化合物 51 的形成。）该合成用于确认 Hakomori 结构的分配，并为免疫偶联铺平了道路。（见化合物 64。）
• Large scale enzymatic synthesis of oligosaccharides
  申请人：Academia Sinica

  公开号：US09340812B2

  公开（公告）日：2016-05-17

  A novel UDP-Gal regeneration process and its combined use with a galactosyltransferase to add galactose to a suitable acceptor substrate. Also described herein are synthetic methods for generating Globo-series oligosaccharides in large scale, wherein the methods may involve the combination of a glycosyltransferase reaction and a nucleotide sugar regeneration process.

  一种新型UDP-Gal再生过程及其与半乳糖基转移酶的联合使用，用于将半乳糖添加到适合的受体底物上。本文还描述了一种用于大规模生成Globo系列寡糖的合成方法，其中该方法可能涉及糖基转移酶反应和核苷酸糖再生过程的组合。
• Effective Sugar Nucleotide Regeneration for the Large-Scale Enzymatic Synthesis of Globo H and SSEA4
  作者：Tsung-I Tsai、Hsin-Yu Lee、Shih-Huang Chang、Chia-Hung Wang、Yu-Chen Tu、Yu-Chen Lin、Der-Ren Hwang、Chung-Yi Wu、Chi-Huey Wong

  DOI：10.1021/ja4075584

  日期：2013.10.2

  development of chemoenzymatic methods for the large-scale synthesis of cancer-associated antigens globopentaose (Gb5), fucosyl-Gb5 (Globo H), and sialyl-Gb5 (SSEA4) by using overexpressed glycosyltransferases coupled with effective regeneration of sugar nucleotides, including UDP-Gal, UDP-GalNAc, GDP-Fuc, and CMP-Neu5Ac. The enzymes used in the synthesis were first identified from different species through

  我们在此报告了通过使用过表达的糖基转移酶和糖核苷酸的有效再生，大规模合成癌症相关抗原 globpentaose (Gb5)、岩藻糖基-Gb5 (Globo H) 和唾液酸-Gb5 (SSEA4) 的化学酶学方法的发展，包括 UDP-Gal、UDP-GalNAc、GDP-Fuc 和 CMP-Neu5Ac。合成中使用的酶首先通过比较研究从不同物种中鉴定出来，然后在大肠杆菌中过表达并分离用于合成。这些方法只需两到三个纯化步骤即可高产地提供数克数量的产品，适用于癌症疫苗和疗法的评估和开发。
• Immunization of Mice with a Fully Synthetic Globo H Antigen Results in Antibodies against Human Cancer Cells: A Combined Chemical—Immunological Approach to the Fashioning of an Anticancer Vaccine
  作者：Govindaswami Ragupathi、Tae Kyo Park、Shengle Zhang、In Jong Kim、Linda Graber、Sucharita Adluri、Kenneth O. Lloyd、Samuel J. Danishefsky、Philip O. Livingston

  DOI：10.1002/anie.199701251

  日期：1997.2.3