Boc-Ser(tBu)-Asn(Trt)-Asn(Trt)-Phe-Ψ(CO-CH2)-Gly-Ala-Ile-Leu-Ser(tBu)-Ser(tBu)-NH2 | 1190430-61-5

• 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: Boc-Ser(tBu)-Asn(Trt)-Asn(Trt)-Phe-Ψ(CO-CH2)-Gly-Ala-Ile-Leu-Ser(tBu)-Ser(tBu)-NH2
• 英文别名: (2S)-2-[[(2S)-1,4-dihydroxy-2-[[(2S)-1-hydroxy-2-[[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]amino]-3-[(2-methylpropan-2-yl)oxy]propylidene]amino]-4-trityliminobutylidene]amino]-N-[(2S)-6-hydroxy-6-[(2S)-1-hydroxy-1-[(2S,3S)-1-hydroxy-1-[(2S)-1-hydroxy-1-[(2S)-1-hydroxy-1-[(2S)-1-hydroxy-1-imino-3-[(2-methylpropan-2-yl)oxy]propan-2-yl]imino-3-[(2-methylpropan-2-yl)oxy]propan-2-yl]imino-4-methylpentan-2-yl]imino-3-methylpentan-2-yl]iminopropan-2-yl]imino-3-oxo-1-phenylhexan-2-yl]-N'-tritylbutanediimidic acid
• CAS: 1190430-61-5
• 化学式: C₉₉H₁₃₀N₁₂O₁₇
• 分子量: 1760.19
• InChiKey: GWYUBOLHGMIPHD-WTRDNWTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  128
• 可旋转键数：
  50
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  457
• 氢给体数：
  13
• 氢受体数：
  29

反应信息

• 作为反应物：
  描述：

  Boc-Ser(tBu)-Asn(Trt)-Asn(Trt)-Phe-Ψ(CO-CH2)-Gly-Ala-Ile-Leu-Ser(tBu)-Ser(tBu)-NH2 在 三异丙基硅烷 、 水 、 三氟乙酸 作用下， 反应 2.0h， 以50%的产率得到H-Ser-Asn-Asn-Phe-Ψ(CO-CH2)-Gly-Ala-Ile-Leu-Ser-Ser-NH2
  参考文献：
  名称：

  Synthesis of a Ketomethylene Isostere of the Fibrillating Peptide SNNFGAILSS

  摘要：

  The direct synthesis of a ketomethylene isostere of the fibril-forming decapeptide SNNFGAILSS is presented with the goal of understanding how small structural changes alter the ability of such peptides to recognize each other for beta-sheet formation. The key synthetic step relies on a SmI2-mediated coupling of a N-tetrapeptidyl oxazolidinone with a simple acrylate followed by deprotection of the carboxylic acid and a peptide coupling step with the pentapeptide H-AILSS-NH2.

  DOI：

  10.1021/jo901466b
• 作为产物：
  描述：

  L-alanyl-L-isoleucyl-L-leucyl-O-tert-butyl-L-seryl-O-tert-butyl-L-serinamide 、 (6S,9S,12S,15S)-6-(tert-butoxymethyl)-2,2-dimethyl-4,7,10,13,16-pentaoxo-9,12-di-[2-oxo-2-(triphenylmethylamino)ethyl]-15-phenylmethyl-3-oxa-5,8,11,14-tetraazanonadecan-19-oic 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， 反应 72.0h， 以29%的产率得到Boc-Ser(tBu)-Asn(Trt)-Asn(Trt)-Phe-Ψ(CO-CH2)-Gly-Ala-Ile-Leu-Ser(tBu)-Ser(tBu)-NH2
  参考文献：
  名称：

  Synthesis of a Ketomethylene Isostere of the Fibrillating Peptide SNNFGAILSS

  摘要：

  The direct synthesis of a ketomethylene isostere of the fibril-forming decapeptide SNNFGAILSS is presented with the goal of understanding how small structural changes alter the ability of such peptides to recognize each other for beta-sheet formation. The key synthetic step relies on a SmI2-mediated coupling of a N-tetrapeptidyl oxazolidinone with a simple acrylate followed by deprotection of the carboxylic acid and a peptide coupling step with the pentapeptide H-AILSS-NH2.

  DOI：

  10.1021/jo901466b

文献信息

• Synthesis of a Ketomethylene Isostere of the Fibrillating Peptide SNNFGAILSS
  作者：Tina Mittag、Daniel E. Otzen、Niels Chr. Nielsen、Troels Skrydstrup

  DOI：10.1021/jo901466b

  日期：2009.10.16

  The direct synthesis of a ketomethylene isostere of the fibril-forming decapeptide SNNFGAILSS is presented with the goal of understanding how small structural changes alter the ability of such peptides to recognize each other for beta-sheet formation. The key synthetic step relies on a SmI2-mediated coupling of a N-tetrapeptidyl oxazolidinone with a simple acrylate followed by deprotection of the carboxylic acid and a peptide coupling step with the pentapeptide H-AILSS-NH2.