2-[1'(S)-(tert-butyloxycarbonylamino)-2'(S)-methylbutyl]-4-carboxy-5-methyloxazole | 252210-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[1'(S)-(tert-butyloxycarbonylamino)-2'(S)-methylbutyl]-4-carboxy-5-methyloxazole
• 英文别名: 5-methyl-2-[(1S,2S)-2-methyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-1,3-oxazole-4-carboxylic acid
• CAS: 252210-81-4
• 化学式: C₁₅H₂₄N₂O₅
• 分子量: 312.366
• InChiKey: KYALYYBNQQDWGA-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[1'(S)-(tert-butyloxycarbonylamino)-2'(S)-methylbutyl]-4-carboxy-5-methyloxazole 、 2-{(S)-1-[(S)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-hydroxy-propionylamino]-ethyl}-thiazole-4-carboxylic acid ethyl ester; compound with trifluoro-acetic acid 在 二苯基磷酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 2-{(S)-1-[(S)-2-((S)-2-{[2-((1S,2S)-1-tert-Butoxycarbonylamino-2-methyl-butyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-methyl-butyrylamino)-3-hydroxy-propionylamino]-ethyl}-thiazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  从海兔Dolabella auricularia合成具有细胞毒性的环六肽dolastatin I

  摘要：

  从日本海兔Dolabella auricularia分离出的细胞毒性环六肽Dolastatin I是对映选择性合成的，证实了其立体结构。

  DOI：

  10.1016/s0040-4020(99)00729-2
• 作为产物：
  描述：

  2-[1'(S)-(tert-butyloxycarbonylamino)-2'(S)-methylbutyl]-4(S)-(methoxycarbonyl)-5-methyloxazoline 在 lithium hydroxide 、 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 2-[1'(S)-(tert-butyloxycarbonylamino)-2'(S)-methylbutyl]-4-carboxy-5-methyloxazole
  参考文献：
  名称：

  Rational Design of Bacitracin A Derivatives by Incorporating Natural Product Derived Heterocycles

  摘要：

  Heterocycles display common structural motifs in nonribosomally produced peptides with an enormous impact on their bioactivity. In the case of the branched cyclic Bacitracin A, the thiazoline moiety is manufactured during NRPS peptide chain elongation. Here we describe a method to selectively alter the heterocyclic metal binding subunit of Bacitracin A by the synthesis of heterocyclic building blocks that were successfully coupled to the linear decapeptide and subsequently cyclized using the excised bacitracin PCP-TE bidomain. Utilization of this cyclase allowed the first generation of branched cyclic bacitracin derivatives containing thiazole and oxazoles. The generated bacitracin derivatives showed bactericidal activity, indicating the possibility of altering the biological important heterocyclic subunit and overcoming existing limitations for the application of bacitracin.

  DOI：

  10.1021/ja062906w

文献信息

• Rational Design of Bacitracin A Derivatives by Incorporating Natural Product Derived Heterocycles
  作者：Björn Wagner、Dirk Schumann、Uwe Linne、Ulrich Koert、Mohamed A. Marahiel

  DOI：10.1021/ja062906w

  日期：2006.8.1

  Heterocycles display common structural motifs in nonribosomally produced peptides with an enormous impact on their bioactivity. In the case of the branched cyclic Bacitracin A, the thiazoline moiety is manufactured during NRPS peptide chain elongation. Here we describe a method to selectively alter the heterocyclic metal binding subunit of Bacitracin A by the synthesis of heterocyclic building blocks that were successfully coupled to the linear decapeptide and subsequently cyclized using the excised bacitracin PCP-TE bidomain. Utilization of this cyclase allowed the first generation of branched cyclic bacitracin derivatives containing thiazole and oxazoles. The generated bacitracin derivatives showed bactericidal activity, indicating the possibility of altering the biological important heterocyclic subunit and overcoming existing limitations for the application of bacitracin.
• Synthesis of dolastatin I, a cytotoxic cyclic hexapeptide from the sea hare Dolabella auricularia
  作者：Hideo Kigoshi、Shiho Yamada

  DOI：10.1016/s0040-4020(99)00729-2

  日期：1999.10

  Dolastatin I, a cytotoxic cyclic hexapeptide isolated from the Japanese sea hare Dolabella auricularia, was enantioselectively synthesized, which confirmed its stereostructure.

  从日本海兔Dolabella auricularia分离出的细胞毒性环六肽Dolastatin I是对映选择性合成的，证实了其立体结构。