N-acetyl-L-prolyl-L-alanyl-L-prolyl-glycine | 216484-20-7

• 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-acetyl-L-prolyl-L-alanyl-L-prolyl-glycine
• CAS: 216484-20-7
• 化学式: C₁₇H₂₆N₄O₆
• 分子量: 382.417
• InChiKey: HNZUOLOLYNOFEB-DRZSPHRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.31
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  136.12
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  O-(2-acetamino-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonyl-L-alanyl-L-prolyl-L-prolyl-L-alanine heptyl ester 、 N-acetyl-L-prolyl-L-alanyl-L-prolyl-glycine 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-acetyl-O-(2-acetamino-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonyl-L-alaninyl-L-prolyl-L-prolyl-L-alanine heptyl ester 、 N-acetyl-L-prolyl-L-alanyl-L-prolyl-glycyl O-(2-acetamino-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonyl-L-alanyl-L-prolyl-L-prolyl-L-alanine heptyl ester
  参考文献：
  名称：

  Effects of glycosylation on fragments of tumour associated human epithelial mucin MUC1

  摘要：

  The glycodecapeptide AcPAPGS(alpha GalNAc)T(alpha GalNAc)APPA and the C-terminal glycohexapeptide AcS(alpha GalNAc)T(alpha GalNAc)APPA have been synthesized by applying the N-terminal Fmoc group in combination with the heptyl ester cleavable by lipase-catalyzed hydrolysis at pH 7. The solution conformation of these MUC1-related synthetic glycopeptides and the control, non-glycosylated decapeptide AcPAPGSTAPPA have been investigated using NMR spectroscopy. The structural studies indicate that the glycohexapeptide has a folded structure in solution. For this molecule, unrestrained molecular dynamics has been used to confirm the presence of the observed solution through-space connections. The results indicate that the non-globular nature of MUC1 is due to both protein core sequence and the effect of carbohydrate. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00092-3
• 作为产物：
  描述：

  L-prolyl-glycine heptyl ester 在 吗啉 、 吡啶 、 lipase N (Rhizopus niveus (Amano)) treated with PMSF 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 68.0h， 生成 N-acetyl-L-prolyl-L-alanyl-L-prolyl-glycine
  参考文献：
  名称：

  Effects of glycosylation on fragments of tumour associated human epithelial mucin MUC1

  摘要：

  The glycodecapeptide AcPAPGS(alpha GalNAc)T(alpha GalNAc)APPA and the C-terminal glycohexapeptide AcS(alpha GalNAc)T(alpha GalNAc)APPA have been synthesized by applying the N-terminal Fmoc group in combination with the heptyl ester cleavable by lipase-catalyzed hydrolysis at pH 7. The solution conformation of these MUC1-related synthetic glycopeptides and the control, non-glycosylated decapeptide AcPAPGSTAPPA have been investigated using NMR spectroscopy. The structural studies indicate that the glycohexapeptide has a folded structure in solution. For this molecule, unrestrained molecular dynamics has been used to confirm the presence of the observed solution through-space connections. The results indicate that the non-globular nature of MUC1 is due to both protein core sequence and the effect of carbohydrate. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00092-3