cyclo[Leu-D-Phe-Pro-D-Lys(Cbz)(Cbz)-Val-Orn(Cbz)(Cbz)-Leu-D-Phe-Pro-D-Lys(Cbz)(Cbz)-Val-Orn(Cbz)(Cbz)] | 1008365-07-8

• 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: cyclo[Leu-D-Phe-Pro-D-Lys(Cbz)(Cbz)-Val-Orn(Cbz)(Cbz)-Leu-D-Phe-Pro-D-Lys(Cbz)(Cbz)-Val-Orn(Cbz)(Cbz)]
• 英文别名: benzyl N-[3-[(3R,6S,9S,12S,15R,18S,24R,27S,30S,33S,36R,39S)-3,24-dibenzyl-6,27-bis(2-methylpropyl)-2,5,8,11,14,17,23,26,29,32,35,38-dodecaoxo-15,36-bis[4-(phenylmethoxycarbonylamino)butyl]-30-[3-(phenylmethoxycarbonylamino)propyl]-12,33-di(propan-2-yl)-1,4,7,10,13,16,22,25,28,31,34,37-dodecazatricyclo[37.3.0.018,22]dotetracontan-9-yl]propyl]carbamate
• CAS: 1008365-07-8
• 化学式: C₁₀₄H₁₄₀N₁₆O₂₀
• 分子量: 1934.35
• InChiKey: GZRHYXGTIMMAFU-VGVIGJNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  140
• 可旋转键数：
  40
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  485
• 氢给体数：
  14
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  cyclo[Leu-D-Phe-Pro-D-Lys(Cbz)(Cbz)-Val-Orn(Cbz)(Cbz)-Leu-D-Phe-Pro-D-Lys(Cbz)(Cbz)-Val-Orn(Cbz)(Cbz)] 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 48.0h， 生成 [D-Lys(6,6')]-gratisin tetrahydrochloride
  参考文献：
  名称：

  Syntheses of low-hemolytic antimicrobial gratisin peptides

  摘要：

  Antibiotic and hemolytic activities of gratisin (GR), cyclo(-Val(1)-Orn(2)-Leu(3)-D-Phe(4)-Pro(5)-D-Tyr(6)-)(2), and. fifteen GR analogues, which have various D-amino acid residues in place of D-Tyr(6,6') residues, were examined. Among them, [D-Orn(6,6')]-GR, [D-Lys(6,6')]-GR and [D-Arg(6,6')]-GR showed the strong activity against both Gram-positive and Gram-negative bacteria. In addition, the antibiotics showed significantly reduced toxicity against human blood cells compared with gramicidin S, cyclo(-Val(1)-Orn(2)-Leu(3)-D-Phe(4)-Pro(5)-)(2). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.133
• 作为产物：
  描述：

  BOC-L-脯氨酸 、 N-Boc-L-缬氨酸 、 BOC-L-亮氨酸 、 N-叔丁氧羰基-N'-苄氧羰基-L-鸟氨酸 、 Boc-D-苯丙氨酸 、 N2-[叔丁氧羰基]-N6-[苄氧羰基]-D-赖氨酸 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 cyclo[Leu-D-Phe-Pro-D-Lys(Cbz)(Cbz)-Val-Orn(Cbz)(Cbz)-Leu-D-Phe-Pro-D-Lys(Cbz)(Cbz)-Val-Orn(Cbz)(Cbz)]
  参考文献：
  名称：

  Syntheses of low-hemolytic antimicrobial gratisin peptides

  摘要：

  Antibiotic and hemolytic activities of gratisin (GR), cyclo(-Val(1)-Orn(2)-Leu(3)-D-Phe(4)-Pro(5)-D-Tyr(6)-)(2), and. fifteen GR analogues, which have various D-amino acid residues in place of D-Tyr(6,6') residues, were examined. Among them, [D-Orn(6,6')]-GR, [D-Lys(6,6')]-GR and [D-Arg(6,6')]-GR showed the strong activity against both Gram-positive and Gram-negative bacteria. In addition, the antibiotics showed significantly reduced toxicity against human blood cells compared with gramicidin S, cyclo(-Val(1)-Orn(2)-Leu(3)-D-Phe(4)-Pro(5)-)(2). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.133

文献信息

• Syntheses of low-hemolytic antimicrobial gratisin peptides
  作者：Makoto Tamaki、Manabu Kokuno、Ichiro Sasaki、Yumiko Suzuki、Michiko Iwama、Kenichi Saegusa、Yusuke kikuchi、Mitsuno Shindo、Masahiro Kimura、Yoshiki Uchida

  DOI：10.1016/j.bmcl.2009.03.133

  日期：2009.5

  Antibiotic and hemolytic activities of gratisin (GR), cyclo(-Val(1)-Orn(2)-Leu(3)-D-Phe(4)-Pro(5)-D-Tyr(6)-)(2), and. fifteen GR analogues, which have various D-amino acid residues in place of D-Tyr(6,6') residues, were examined. Among them, [D-Orn(6,6')]-GR, [D-Lys(6,6')]-GR and [D-Arg(6,6')]-GR showed the strong activity against both Gram-positive and Gram-negative bacteria. In addition, the antibiotics showed significantly reduced toxicity against human blood cells compared with gramicidin S, cyclo(-Val(1)-Orn(2)-Leu(3)-D-Phe(4)-Pro(5)-)(2). (C) 2009 Elsevier Ltd. All rights reserved.