L-prolyl-L-prolyl-L-alanine heptyl ester | 139937-88-5

• 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: L-prolyl-L-prolyl-L-alanine heptyl ester
• 英文别名: heptyl (2S)-2-[[(2S)-1-[(2S)-pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]propanoate
• CAS: 139937-88-5
• 化学式: C₂₀H₃₅N₃O₄
• 分子量: 381.516
• InChiKey: SPRYVEBJAUWDIU-ULQDDVLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-prolyl-L-prolyl-L-alanine heptyl ester 、 在 1-羟基苯并三唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以50%的产率得到N-(9-fluorenylmethyloxycarbonyl)-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：

  N-(9-fluorenylmethoxycarbonyl)-L-prolyl-L-alanine heptyl ester 在 吗啉 、 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 50.0h， 生成 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

文献信息

• Waldmann, H; Heuser, A; Braun, P, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 12, p. 799 - 802
  作者：Waldmann, H、Heuser, A、Braun, P、Kunz, H

  DOI：——

  日期：——