Galβ1-3GalNAcα-O-TVPAAVVVA-CONH2 | 1070177-91-1

• 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: Galβ1-3GalNAcα-O-TVPAAVVVA-CONH2
• 英文别名: (2S)-1-[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-aminobutanoyl]amino]-3-methylbutanoyl]-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
• CAS: 1070177-91-1
• 化学式: C₅₂H₉₁N₁₁O₂₀
• 分子量: 1190.36
• InChiKey: NXQBGAPESPNYKD-OPWCSMMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  83
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  481
• 氢给体数：
  16
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-L-丙氨酸 、 Fmoc-L-脯氨酸 、 N^α-fluoren-9-ylmethoxycarbonyl-O-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-galactopyranosyl]-L-threonine 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 哌啶 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 Galβ1-3GalNAcα-O-TVPAAVVVA-CONH2
  参考文献：
  名称：

  Structure−Activity Relationship Studies for the Peptide Portion of the Bladder Epithelial Cell Antiproliferative Factor from Interstitial Cystitis Patients

  摘要：

  We performed comprehensive structure-activity relationship (SAR) studies on the peptide portion of antiproliferative factor (APF), a sialylated frizzled-8 related glycopeptide that inhibits normal bladder epithelia] and urothelial carcinoma cell proliferation. Glycopeptide derivatives were synthesized by solid-phase methods using standard Fmoc chemistry and purified by RP-HPLC; all intermediate and final products were verified by HPLC-MS and NMR analyses. Antiproliferative activity of each derivative was determined by inhibition of (3)H-thymidine incorporation in primary normal human bladder epithelial cells. Structural components of the peptide segment of APF that proved to be important for biological activity included the presence of at least eight of the nine N-terminal amino acids, a negative charge in the C-terminal amino acid, a free amino group at the N-terminus, maintenance of a specific amino acid sequence in the C-terminal tail, and trans conformation for the peptide bonds. These data provide critical guidelines for optimization of structure in design of APF analogues as potential therapeutic agents.

  DOI：

  10.1021/jm8002763

文献信息

• Structure−Activity Relationship Studies for the Peptide Portion of the Bladder Epithelial Cell Antiproliferative Factor from Interstitial Cystitis Patients
  作者：Piotr Kaczmarek、Susan K. Keay、Gillian M. Tocci、Kristopher R. Koch、Chen-Ou Zhang、Joseph J. Barchi、David Grkovic、Li Guo、Christopher J. Michejda

  DOI：10.1021/jm8002763

  日期：2008.10.9

  We performed comprehensive structure-activity relationship (SAR) studies on the peptide portion of antiproliferative factor (APF), a sialylated frizzled-8 related glycopeptide that inhibits normal bladder epithelia] and urothelial carcinoma cell proliferation. Glycopeptide derivatives were synthesized by solid-phase methods using standard Fmoc chemistry and purified by RP-HPLC; all intermediate and final products were verified by HPLC-MS and NMR analyses. Antiproliferative activity of each derivative was determined by inhibition of (3)H-thymidine incorporation in primary normal human bladder epithelial cells. Structural components of the peptide segment of APF that proved to be important for biological activity included the presence of at least eight of the nine N-terminal amino acids, a negative charge in the C-terminal amino acid, a free amino group at the N-terminus, maintenance of a specific amino acid sequence in the C-terminal tail, and trans conformation for the peptide bonds. These data provide critical guidelines for optimization of structure in design of APF analogues as potential therapeutic agents.