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Ac-YVRTPPKSPSS-NH2 | 1569310-51-5

中文名称
——
中文别名
——
英文名称
Ac-YVRTPPKSPSS-NH2
英文别名
Ac-YVRTPPKSPSS-NH2
Ac-YVRTPPKSPSS-NH2化学式
CAS
1569310-51-5
化学式
C56H90N16O17
mdl
——
分子量
1259.43
InChiKey
OHMIAMDLLNSJBS-NBCDBSNJSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    -7.3
  • 重原子数:
    89.0
  • 可旋转键数:
    34.0
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.66
  • 拓扑面积:
    525.89
  • 氢给体数:
    18.0
  • 氢受体数:
    19.0

反应信息

  • 作为产物:
    描述:
    Fmoc-L-缬氨酸N-trityl-L-serineFmoc-L-脯氨酸乙酸酐N-triphenylmethyl-(L)-threonine 、 alkaline earth salt of/the/ methylsulfuric acid 、 alkaline earth salt of/the/ methylsulfuric acid 、 alkaline earth salt of/the/ methylsulfuric acid 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺哌啶 作用下, 以 N,N-二甲基甲酰胺 为溶剂, 生成 Ac-YVRTPPKSPSS-NH2
    参考文献:
    名称:
    OGlcNAcylation and Phosphorylation Have Opposing Structural Effects in tau: Phosphothreonine Induces Particular Conformational Order
    摘要:
    Phosphorylation and OGlcNAcylation are dynamic intracellular protein post-translational modifications that frequently are alternatively observed on the same serine and threonine residues. Phosphorylation and OGlcNAcylation commonly occur in natively disordered regions of proteins, and often have opposing functional effects. In the microtubule-associated protein tau, hyperphosphorylation is associated with protein misfolding and aggregation as the neurofibrillary tangles of Alzheimer's disease, whereas OGlcNAcylation stabilizes the soluble form of tau. A series of peptides derived from the proline-rich domain (residues 174-251) of tau was synthesized, with free Ser/Thr hydroxyls, phosphorylated Ser/Thr (pSer/pThr), OGlcNAcylated Ser/Thr, and diethylphosphorylated Ser/Thr. Phosphorylation and OGlcNAcylation were found by CD and NMR to have opposing structural effects on polyproline helix (PPII) formation, with phosphorylation favoring PPII, OGlcNAcylation opposing PPII, and the free hydroxyls intermediate in structure, and with phosphorylation structural effects greater than OGlcNAcylation. For tau(196-209), phosphorylation and OGlcNAcylation had similar structural effects, opposing a nascent alpha-helix. Phosphomimic Glu exhibited PPII-favoring structural effects. Structural changes due to Thr phosphorylation were greater than those of Ser phosphorylation or Glu, with particular conformational restriction as the dianion, with mean (3)J(alpha N) = 3.5 Hz (pThr) versus 5.4 Hz (pSer), compared to 7.2, 6.8, and 6.2 Hz for Thr, Ser, and Glu, respectively, values that correlate with the backbone torsion angle phi. Dianionic phosphothreonine induced strong phosphothreonine amide protection and downfield amide chemical shifts (delta(mean) = 9.63 ppm), consistent with formation of a stable phosphate-amide hydrogen bond. These data suggest potentially greater structural importance of threonine phosphorylation than serine phosphorylation due to larger induced structural effects.
    DOI:
    10.1021/ja407156m
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