N-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl)-L-threonine tert-butyl ester | 120851-32-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl)-L-threonine tert-butyl ester
• 英文别名: N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-β-D-galactopyranosyl)-1-threonine tert-butyl ester；N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl)-L-threonine tert-butyl ester；N-(9-Fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-β-D-galactopyranosyl)-L-threonin-tert-butylester
• CAS: 120851-32-3
• 化学式: C₃₅H₄₂N₄O₁₂
• 分子量: 710.738
• InChiKey: MNTRKMMELRHQEQ-XXMGXVELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  51.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  210.75
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  D-(+)-galactosamine hydrochloride 在 吡啶 、 乙醚 、 三氟甲磺酸三甲基硅酯 、 triflic azide 、 乙酸肼 、 potassium carbonate 、 copper(II) sulfate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl)-L-threonine tert-butyl ester
  参考文献：
  名称：

  Xu, Ran; Hanson, Sarah R.; Zhang, Zhiwen, Journal of the American Chemical Society, 2004, vol. 126, # 48, p. 15654 - 15655

  摘要：

  DOI：

文献信息

• Functional and Structural Characterization of Drosocin and its Derivatives Linked O-GalNAc at Thr¹¹Residue
  作者：Mi-Ja Ahn、Ho-Ik Sohn、Yong Hai Nan、Ravichandran N. Murugan、Chae-Joon Cheong、Eun-Kyoung Ryu、Eun-Hee Kim、Shin-Won Kang、Eun-Joo Kim、Song-Yub Shin、Jeong-Kyu Bang

  DOI：10.5012/bkcs.2011.32.9.3327

  日期：2011.9.20

  Antimicrobial peptides have recently gained the much attention because of their ability to make defense system from attacking bacterial infections. Drosocin has been considered as very attractive antibiotic agents because of low toxicity against human erythrocytes and active at the low concentration. We have studied the structureactivity relationship of a glycopeptide drosocin focused on the N-acetyl-D-galactoside at $Thr^11}$ residue. Based on the radial diffusion assay, we found that the acetylation of carbohydrate moiety increased the antimicrobial activity and the $Pro^10}$, present in the middle of drosocin plays an important role in the antimicrobial activity. Our results provide a good lead compound for further studies on the design of drosocin-based analogues targeting glyco linked Thr site.

  抗菌肽最近受到了广泛关注，因为它们能够保护防御系统免受细菌感染的攻击。由于对人类红细胞的低毒性以及在低浓度下的活性，drosocin被认为是非常有吸引力的抗生素。我们研究了一种糖肽drosocin的结构活性关系，重点关注位于$Thr^11}$残基上的N-乙酰-D-半乳糖苷。基于径向扩散实验，我们发现碳水化合物成分的乙酰化提高了抗菌活性，而位于drosocin中间的$Pro^10}$在抗菌活性中起着重要作用。我们的结果为进一步研究以drosocin为基础的类似物设计靶向糖链接的Thr位点提供了良好的先导化合物。
• Solid-Phase Synthesis of a Sialyl-Tn-Glycoundecapeptide of the MUC1 Repeating Unit
  作者：Beate Liebe、Horst Kunz

  DOI：10.1002/hlca.19970800511

  日期：1997.8.11

  The synthesis of glycopeptides carrying tumour-associated antigens is of interest for cancer diagnosis and treatment. Here, a very efficient route lo disaccharide threonine building block 8 is presented which allows the introduction of the sialyl-Tn antigen into a peptide. The syntheses of the undecapeptide and the sialyl-Tn-containing glycoundecapeptide, which are a part of the repeating unit of MUC1

  携带肿瘤相关抗原的糖肽的合成对于癌症的诊断和治疗很重要。在此，提出了非常有效的二糖苏氨酸构建模块8的途径，其允许将唾液酸-Tn抗原引入肽中。作为MUC1重复单元的一部分的十一肽和含唾液酸基-Tn的糖十一肽的合成，是通过固相合成并利用在中性条件下可裂解的烯丙基锚进行的。从树脂上脱离后，肽和糖肽完全脱保护，分别得到目标化合物13和15。
• One-Pot Azidochlorination of Glycals
  作者：Carolin Plattner、Michael Höfener、Norbert Sewald

  DOI：10.1021/ol102750h

  日期：2011.2.18

  A simple one-pot azidochlorination for the preparation of nitrogen-containing Koenigs−Knorr glycosyl donors proceeds upon reaction of protected glycals with sodium azide, ferric chloride, and hydrogen peroxide. Different mono- and disaccharide galactals and glucals are converted in a highly α-selective manner to the 2-azido glycosyl chlorides. Starting from disaccharide galactals, building blocks for

  在保护的糖与叠氮化钠，氯化铁和过氧化氢反应后，即可进行简单的一锅式叠氮氯化，以制备含氮的Koenigs-Knorr糖基供体。将不同的单糖和二糖半乳糖和葡糖以高度α-选择性的方式转化为2-叠氮基糖基氯化物。从二糖半乳糖开始，以直接的方式获得用于合成T-抗原的构件。反应条件的简单性允许2-叠氮基取代的糖基氯的有效且可扩展的α-选择性合成。
• Chemoenzymatic synthesis of glycosylphosphatidylinositol-anchored glycopeptides
  作者：Zhimeng Wu、Xueqing Guo、Zhongwu Guo

  DOI：10.1039/c0cc00828a

  日期：——

  MUC1 glycopeptide was efficiently coupled to glycosylphosphatidylinositol (GPI) derivatives by sortase A (SrtA), verifying that SrtA can accept sterically hindered glycopeptide as substrate for ligation with GPIs. This work has established a practical method for the chemoenzymatic synthesis of GPI-linked glycopeptides.

  MUC1 糖肽通过分选酶 A (SrtA) 与糖基磷脂酰肌醇 (GPI) 衍生物有效偶联，验证了 SrtA 可以接受空间位阻糖肽作为与 GPI 连接的底物。这项工作为化学酶法合成 GPI 连接的糖肽建立了一种实用的方法。
• Paulsen, Hans; Adermann, Knut, Liebigs Annalen der Chemie, 1989, p. 751 - 770
  作者：Paulsen, Hans、Adermann, Knut

  DOI：——

  日期：——