Fmoc-Ser(O-GlcNAc)-OH | 196098-23-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Fmoc-Ser(O-GlcNAc)-OH
• 英文别名: Nα-Fmoc-Ser(OGlcNAc)；(2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 196098-23-4
• 化学式: C₂₆H₃₀N₂O₁₀
• 分子量: 530.532
• InChiKey: HKZFWMGMCKCIJY-QULIQSTESA-N

物化性质

• 沸点：
  884.4±65.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  184
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Fmoc-Ser(O-GlcNAc)-OH 在 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.0h， 生成 allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((6R,8R,8aS)-7-acetamido-8-hydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yloxy)propanoate
  参考文献：
  名称：

  METHOD OF PREPARING GLYCOPEPTIDES

  摘要：

  公开号：

  EP1996609B1
• 作为产物：
  描述：

  β-D-葡萄糖胺五乙酸酯 在 MS 4 Angstroem 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 生成 Fmoc-Ser(O-GlcNAc)-OH
  参考文献：
  名称：

  MAdCAM-1 粘蛋白结构域的 O-糖肽的化学酶促溶液和固相合成。O-LacNAc、O-Sialyl-LacNAc 和 O-Sialyl-Lewis-X 肽的一般途径

  摘要：

  描述了一种用于固相合成含有 O 连接唾液酸-刘易斯-X (SLex) 四糖的糖肽的有效和通用方法。使用组合化学酶法，首次合成了非天然 β-O 连接的 SLex，该 SLex 连接到 L-选择素配体 MAdCAM-1 的粘蛋白结构域的部分序列。树脂结合的 O-糖缀合物由新的 Fmoc-苏氨酸结构单元合成，该结构单元带有 O-未保护的 β-连接的 N-乙酰葡萄糖胺 (GlcNAc) 部分。酸和碱稳定的 HYCRON 接头能够完全去除固相上的所有保护基团。糖基转移酶用于在支持和未支持的 O-GlcNAc-八肽底物上扩展聚糖。酸和碱敏感的 O-糖肽在几乎中性的条件下释放，利用钯（0）催化的烯丙基键断裂。具有O-乙酰基-pr的酯连接糖肽的选择性O-脱乙酰化研究

  DOI：

  10.1021/ja971383c

文献信息

• A silyl ether-protected building block for <i>O</i>-GlcNAcylated peptide synthesis to enable one-pot acidic deprotection
  作者：Bingjia Yan、Wenyi Li、Christian P. R. Hackenberger

  DOI：10.1039/d1ob00510c

  日期：——

  building block for Fmoc/tBu solid phase peptide synthesis (SPPS) of β-linked O-GlcNAcylated peptides. This building block carries acid labile silyl ether protecting groups, which are fully removed under TFA-mediated peptide cleavage conditions from the resin, thus requiring fewer synthetic steps and no intermediate purification as compared to other acid or base labile protecting group strategies.

  在本报告中，我们介绍了一种用于 β-连接O -GlcNA 酰化肽的 Fmoc/ t Bu 固相肽合成 (SPPS) 的新型构建模块。该结构单元带有酸不稳定的甲硅烷基醚保护基，在 TFA 介导的肽裂解条件下从树脂中完全去除，因此与其他酸或碱不稳定的保护基策略相比，需要更少的合成步骤，并且无需中间纯化。
• Second-Generation Sugar-Assisted Ligation: A Method for the Synthesis of Cysteine-Containing Glycopeptides
  作者：Simon Ficht、Richard J. Payne、Ashraf Brik、Chi-Huey Wong

  DOI：10.1002/anie.200700546

  日期：2007.8.3
• Carbohydrate−π Interactions: What Are They Worth?
  作者：Zachary R. Laughrey、Sarah E. Kiehna、Alex J. Riemen、Marcey L. Waters

  DOI：10.1021/ja803960x

  日期：2008.11.5

  Protein-carbohydrate interactions play an important role in many biologically important processes. The recognition is mediated by a number of noncovalent interactions, including an interaction between the a-face of the carbohydrate and the aromatic side chain of the protein. To elucidate this interaction, it has been studied in the context of a beta-hairpin in aqueous solution, in which the interaction can be investigated in the absence of other cooperative noncovalent interactions. In this beta-hairpin system, both the aromatic side chain and the carbohydrate were varied in an effort to gain greater insight into the driving force and magnitude of the carbohydrate-pi interaction. The magnitude of the interaction was found to vary from -0.5 to -0.8 kcal/mol, depending on the nature of the aromatic ring and the carbohydrate. Replacement of the aromatic ring with an aliphatic group resulted in a decrease in interaction energy to -0.1 kcal/mol, providing evidence for the contribution of CH-pi interactions to the driving force. These findings demonstrate the significance of carbohydrate-pi interactions within biological systems and also their utility as a molecular recognition element in designed systems.
• A simplified procedure for gram-scale production of sialylglycopeptide (SGP) from egg yolks and subsequent semi-synthesis of Man3GlcNAc oxazoline
  作者：Bingyang Sun、Wenzheng Bao、Xiaobo Tian、Mingjing Li、Hong Liu、Jinhua Dong、Wei Huang

  DOI：10.1016/j.carres.2014.07.013

  日期：2014.9

  Heterogeneity of glycan structures in native glycoconjugates always hampers precise studies on carbohydrate-involved biological functions. To construct homogeneous glycoconjugates from natural resource of homogeneous glycans is therefore a practical approach to solve this problem. We report here an optimized procedure for gram-scale production of sialylglycopeptide (SGP) containing a disialyl biantennary complex-type N-glycan from egg yolks. Our new procedure simplified the extraction process by treating the egg yolk powder with 40% acetone, avoiding massive emulsification, high-speed centrifugation, and sophisticated chromatography in reported methods. Subsequent semi-synthesis of the N-glycan core Man3GlcNAc oxazoline from SGP was accomplished for the first-time via glyco-trimming and successive oxazoline formation. This efficient semi-synthesis provides an alternative to the pure chemical approach that involves multi-step total synthesis and facilitates the application of endo-glycosidase-enabled chemoenzymatic synthesis of various homogeneous glycoconjugates.
• METHOD OF PREPARING GLYCOPEPTIDES
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：EP1996609B1

  公开（公告）日：2016-08-03