{(S)-1-[(S)-5-Benzoylamino-1-((1S,2R)-1-carbamoyl-2-hydroxy-propylcarbamoyl)-pentylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid tert-butyl ester | 219319-39-8

• 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: {(S)-1-[(S)-5-Benzoylamino-1-((1S,2R)-1-carbamoyl-2-hydroxy-propylcarbamoyl)-pentylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid tert-butyl ester
• CAS: 219319-39-8
• 化学式: C₂₆H₄₀N₆O₈
• 分子量: 564.639
• InChiKey: KZVYMWAAZGRHDF-HYJFEMIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.81
• 重原子数：
  40.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  232.04
• 氢给体数：
  7.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  {(S)-1-[(S)-5-Benzoylamino-1-((1S,2R)-1-carbamoyl-2-hydroxy-propylcarbamoyl)-pentylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid tert-butyl ester 在 三乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (S)-2-Benzoylamino-N¹-[(S)-5-benzoylamino-1-((1S,2R)-1-carbamoyl-2-hydroxy-propylcarbamoyl)-pentyl]-succinamide
  参考文献：
  名称：

  The design, synthesis, and initial evaluation of benzophenone-containing peptides as potential photoaffinity labels of oligosaccharyltransferase

  摘要：

  The benzophenone photophore was incorporated into protected tripeptides and tetrapeptides as photoactivatable probes to study the multimeric enzyme oligosaccharyltransferase (OST). These peptides contain the -Asn-X-Thr- sequon which is required for OST-catalyzed N-glycosylation. Two tripeptides, Bz-Asn-Bpa-Thr-NH2 (3b) and Bz-Asn-Lys[N-epsilon-(4-Bz)Bz]-Thr-NH2 (4b), were found to be good OST substrates. They were competitive inhibitors versus standard peptide substrate [C-14]Bz-Asn-Leu-Thr-NH2 and their K-i values were determined to be 41 +/- 61 mu M and 21 +/- 6 mu M, respectively, using synthetic (GlcNAc)(2)-PP-dolichol.. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00135-7
• 作为产物：
  描述：

  BOC-L-天冬酰胺 、 N-[(S)-5-Amino-5-((1S,2R)-1-carbamoyl-2-hydroxy-propylcarbamoyl)-pentyl]-benzamide; compound with trifluoro-acetic acid 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到{(S)-1-[(S)-5-Benzoylamino-1-((1S,2R)-1-carbamoyl-2-hydroxy-propylcarbamoyl)-pentylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  The design, synthesis, and initial evaluation of benzophenone-containing peptides as potential photoaffinity labels of oligosaccharyltransferase

  摘要：

  The benzophenone photophore was incorporated into protected tripeptides and tetrapeptides as photoactivatable probes to study the multimeric enzyme oligosaccharyltransferase (OST). These peptides contain the -Asn-X-Thr- sequon which is required for OST-catalyzed N-glycosylation. Two tripeptides, Bz-Asn-Bpa-Thr-NH2 (3b) and Bz-Asn-Lys[N-epsilon-(4-Bz)Bz]-Thr-NH2 (4b), were found to be good OST substrates. They were competitive inhibitors versus standard peptide substrate [C-14]Bz-Asn-Leu-Thr-NH2 and their K-i values were determined to be 41 +/- 61 mu M and 21 +/- 6 mu M, respectively, using synthetic (GlcNAc)(2)-PP-dolichol.. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00135-7