Fmoc-D-Ser(Ac3GlcNAcβ)-OH | 1370339-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Fmoc-D-Ser(Ac3GlcNAcβ)-OH
• 英文别名: (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propanoic acid；(2R)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 1370339-20-0
• 化学式: C₃₂H₃₆N₂O₁₃
• 分子量: 656.643
• InChiKey: ORICVOOXZDVFIP-HATSJDEBSA-N

物化性质

• 沸点：
  856.8±65.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  202.09
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Fmoc-D-Ser(Ac3GlcNAcβ)-OH 、 Fmoc-甘氨酸 、 Fmoc-L-脯氨酸五氟苯酯 、 芴甲氧羰酰基-6-氨基己酸 在 N,N-二异丙基乙胺 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 生成 Fmoc-D-Ser(Ac3GlcNAcβ)-Pro-Gly-Hex-OH
  参考文献：
  名称：

  Enhanced Epimerization of Glycosylated Amino Acids During Solid-Phase Peptide Synthesis

  摘要：

  Glycopeptides are extremely useful for basic research and clinical applications, but access to structurally defined glycopeptides is limited by the difficulties in synthesizing this class of compounds. In this study, we demonstrate that many common peptide coupling conditions used to prepare O-linked glycopeptides result in substantial amounts of epimerization at the a position. In fact, epimerization resulted in up to 80% of the non-natural epimer, indicating that it can be the major product in some reactions. Through a series of mechanistic studies, we demonstrate that the enhanced epimerization relative to nonglycosylated amino acids is due to a combination of factors, including a faster rate of epimerization, an energetic preference for the unnatural epimer over the natural epimer, and a slower overall rate of peptide coupling. In addition, we demonstrate that use of 2,4,6-trimethylpyridine (TMP) as the base in peptide couplings produces glycopeptides with high efficiency and low epimerization. The information and improved reaction conditions will facilitate the preparation of glycopeptides as therapeutic compounds and vaccine antigens.

  DOI：

  10.1021/ja212188r
• 作为产物：
  描述：

  2-乙酰氨基-1,3,4,6-O-四乙酰基-2-脱氧-alpha-D-吡喃葡萄糖 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 Fmoc-D-Ser(Ac3GlcNAcβ)-OH
  参考文献：
  名称：

  用于 O-GlcNA 酰化肽合成的甲硅烷基醚保护结构单元，可实现一锅酸性脱保护

  摘要：

  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。

  DOI：

  10.1039/d1ob00510c

文献信息

• O-GlcNAc Peptide Epoxyketones Are Recognized by Mammalian Proteasomes
  作者：Martin D. Witte、Bogdan I. Florea、Martijn Verdoes、Oloruntosin Adeyanju、Gijs A. Van der Marel、Herman S. Overkleeft

  DOI：10.1021/ja901231w

  日期：2009.9.2

  Cytosolic and nuclear proteins may be subject to both O-GlcNAcylation and proteasomal degradation. By means of activity-based profiling, we demonstrate that O-GlcNAc serine-containing peptide epoxyketones bind to the proteasome catalytic active sites and thus provide the first clear evidence that proteasomes recognize peptides post-translationally modified with a GlcNAc moiety.