H-D-Ala-Phe(4-Br)-Pro-D-Val-Val-D-Trp-Arg-D-Cys(O3H)-Thr(1)-N(Me)Gln-D-Phe-Thr-Asn-Sar-(1) | 1094480-61-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: H-D-Ala-Phe(4-Br)-Pro-D-Val-Val-D-Trp-Arg-D-Cys(O3H)-Thr(1)-N(Me)Gln-D-Phe-Thr-Asn-Sar-(1)
• 英文别名: (2S)-3-[[(6S,9S,12R,15S,18S,19R)-6-(2-amino-2-oxoethyl)-15-(3-amino-3-oxopropyl)-12-benzyl-9-[(1R)-1-hydroxyethyl]-4,16,19-trimethyl-2,5,8,11,14,17-hexaoxo-1-oxa-4,7,10,13,16-pentazacyclononadec-18-yl]amino]-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-2-[[(2R)-2-aminopropanoyl]amino]-3-(4-bromophenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-oxopropane-1-sulfonic acid
• CAS: 1094480-61-1
• 化学式: C₇₇H₁₀₉BrN₂₀O₂₁S
• 分子量: 1762.8
• InChiKey: YSMMROQFLQXRKM-MSIRBYGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  120
• 可旋转键数：
  36
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  651
• 氢给体数：
  19
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  甲酸氰甲酯 、 H-D-Ala-Phe(4-Br)-Pro-D-Val-Val-D-Trp-Arg-D-Cys(O3H)-Thr(1)-N(Me)Gln-D-Phe-Thr-Asn-Sar-(1) 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以60%的产率得到(2S)-N-[(2R)-1-[(2S)-1-[(2R)-1-[(2S)-1-[(2S)-1-[[(6S,9S,12R,15S,18S,19R)-12-benzyl-8,11,14-trihydroxy-9-[(1R)-1-hydroxyethyl]-6-(2-hydroxy-2-iminoethyl)-15-(3-hydroxy-3-iminopropyl)-4,16,19-trimethyl-2,5,17-trioxo-1-oxa-4,7,10,13,16-pentazacyclononadeca-7,10,13-trien-18-yl]imino]-1-hydroxy-3-sulfopropan-2-yl]imino-5-carbamimidamido-1-hydroxypentan-2-yl]imino-1-hydroxy-3-(1H-indol-3-yl)propan-2-yl]imino-1-hydroxy-3-methylbutan-2-yl]imino-1-hydroxy-3-methylbutan-2-yl]-1-[(2S)-3-(4-bromophenyl)-2-[[(2R)-1-hydroxy-2-(hydroxymethylideneamino)propylidene]amino]propanoyl]pyrrolidine-2-carboximidic acid
  参考文献：
  名称：

  Total Synthesis of Halicylindramide A

  摘要：

  A rapid and efficient Fmoc solid-phase synthesis of halicylindramide A is described. The strategy comprises resin attachment of the first amino acid via the side chain of aspartic acid, stepwise solid-phase synthesis of the linear peptide analog LIP to the cysteine residue, on-resin head-to-tail cyclization and linear peptide synthesis of the N-terminal region, and finally cysteine oxidation and formylation. The stereochemistry of the halicylindramide A was confirmed by comparison of NMR and RP-HPLC data with the natural molecule. A distinctive conformational change was observed from the CD spectra of the halicylindramide A in sodium dodecyl sulfate.

  DOI：

  10.1021/jo802213q
• 作为产物：
  描述：

  (2S)-N-[(2R)-1-[(2S)-1-[(2R)-1-[(2S)-1-[(2S)-1-[[(6S,9S,12R,15S,18S,19R)-12-benzyl-8,11,14-trihydroxy-9-[(1R)-1-hydroxyethyl]-6-(2-hydroxy-2-iminoethyl)-15-(3-hydroxy-3-iminopropyl)-4,16,19-trimethyl-2,5,17-trioxo-1-oxa-4,7,10,13,16-pentazacyclononadeca-7,10,13-trien-18-yl]imino]-1-hydroxy-3-sulfopropan-2-yl]imino-5-carbamimidamido-1-hydroxypentan-2-yl]imino-1-hydroxy-3-(1H-indol-3-yl)propan-2-yl]imino-1-hydroxy-3-methylbutan-2-yl]imino-1-hydroxy-3-methylbutan-2-yl]-1-[(2S)-3-(4-bromophenyl)-2-[[(2R)-1-hydroxy-2-(hydroxymethylideneamino)propylidene]amino]propanoyl]pyrrolidine-2-carboximidic acid 在 mercury(II) diacetate 、 溶剂黄146 、 过甲酸 、 水 、 三异丙基硅烷 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以10 mg的产率得到H-D-Ala-Phe(4-Br)-Pro-D-Val-Val-D-Trp-Arg-D-Cys(O3H)-Thr(1)-N(Me)Gln-D-Phe-Thr-Asn-Sar-(1)
  参考文献：
  名称：

  Total Synthesis of Halicylindramide A

  摘要：

  A rapid and efficient Fmoc solid-phase synthesis of halicylindramide A is described. The strategy comprises resin attachment of the first amino acid via the side chain of aspartic acid, stepwise solid-phase synthesis of the linear peptide analog LIP to the cysteine residue, on-resin head-to-tail cyclization and linear peptide synthesis of the N-terminal region, and finally cysteine oxidation and formylation. The stereochemistry of the halicylindramide A was confirmed by comparison of NMR and RP-HPLC data with the natural molecule. A distinctive conformational change was observed from the CD spectra of the halicylindramide A in sodium dodecyl sulfate.

  DOI：

  10.1021/jo802213q