(2R,6S)-N²,N⁶-bis(fluoren-9-ylmethoxycarbonyl)lanthionine α-allyl ester | 881996-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2R,6S)-N²,N⁶-bis(fluoren-9-ylmethoxycarbonyl)lanthionine α-allyl ester
• 英文别名: (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-prop-2-enoxypropyl]sulfanylpropanoic acid
• CAS: 881996-33-4
• 化学式: C₃₉H₃₆N₂O₈S
• 分子量: 692.789
• InChiKey: HDKYRGYJZLIRGB-OIDHKYIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  166
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,6S)-N²,N⁶-bis(fluoren-9-ylmethoxycarbonyl)lanthionine α-allyl ester 、 FMOC-O-叔丁基-L-丝氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 肉豆蔻酸 生成 (S)-3-{(R)-2-[(S)-1-((S)-5-Amino-1-{(S)-5-amino-1-[(S)-5-amino-1-((S)-5-amino-1-carbamoyl-pentylcarbamoyl)-pentylcarbamoyl]-pentylcarbamoyl}-pentylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-2-icosanoylamino-ethylsulfanyl}-2-icosanoylamino-propionic acid
  参考文献：
  名称：

  Lipolanthionine Peptides Act as Inhibitors of TLR2-Mediated IL-8 Secretion. Synthesis and Structure−Activity Relationships

  摘要：

  Lipoproteins from Gram-positive and -negative bacteria, mycoplasma, and shorter synthetic lipopeptide analogues activate cells of the innate immune system via the Toll-like receptor TLR2/TLR1 or TLR2/TLR6 heterodimers. For this reason, these compounds constitute highly active adjuvants for vaccines either admixed or covalently linked. The lanthionine scaffold has structural similarity with the S-(2,3-dihydroxypropyl)cysteine core structure of the lipopeptides. Therefore, lanthionine-based lipopeptide amides were synthesized and probed for activity as potential TLR2 agonists or antagonists. A collection of analytically defined lipolanthionine peptide amides exhibited an inhibitory effect of the TLR2-mediated IL-8 secretion when applied in high molar excess to the agonistic synthetic lipopeptide Pam(3)Cys-Ser-(LyS)(4)-OH. Structure-activity relationships revealed the influence of the chirality of the two alpha-carbon atoms, the chain lengths of the attached fatty acids and fatty amines, and the oxidation level of the sulfur atom on the inhibitory activity of the lipolanthionine peptide amides.

  DOI：

  10.1021/jm050585d
• 作为产物：
  描述：

  (2R,6S)-N²,N⁶-bis(fluoren-9-ylmethoxycarbonyl)lanthionine ε-allyl α-tert-butyl diester 在 三氟乙酸 作用下， 反应 1.0h， 以389 mg的产率得到(2R,6S)-N²,N⁶-bis(fluoren-9-ylmethoxycarbonyl)lanthionine α-allyl ester
  参考文献：
  名称：

  Lipolanthionine Peptides Act as Inhibitors of TLR2-Mediated IL-8 Secretion. Synthesis and Structure−Activity Relationships

  摘要：

  Lipoproteins from Gram-positive and -negative bacteria, mycoplasma, and shorter synthetic lipopeptide analogues activate cells of the innate immune system via the Toll-like receptor TLR2/TLR1 or TLR2/TLR6 heterodimers. For this reason, these compounds constitute highly active adjuvants for vaccines either admixed or covalently linked. The lanthionine scaffold has structural similarity with the S-(2,3-dihydroxypropyl)cysteine core structure of the lipopeptides. Therefore, lanthionine-based lipopeptide amides were synthesized and probed for activity as potential TLR2 agonists or antagonists. A collection of analytically defined lipolanthionine peptide amides exhibited an inhibitory effect of the TLR2-mediated IL-8 secretion when applied in high molar excess to the agonistic synthetic lipopeptide Pam(3)Cys-Ser-(LyS)(4)-OH. Structure-activity relationships revealed the influence of the chirality of the two alpha-carbon atoms, the chain lengths of the attached fatty acids and fatty amines, and the oxidation level of the sulfur atom on the inhibitory activity of the lipolanthionine peptide amides.

  DOI：

  10.1021/jm050585d

文献信息

• Lipolanthionine Peptides Act as Inhibitors of TLR2-Mediated IL-8 Secretion. Synthesis and Structure−Activity Relationships
  作者：Tobias Seyberth、Söhnke Voss、Roland Brock、Karl-Heinz Wiesmüller、Günther Jung

  DOI：10.1021/jm050585d

  日期：2006.3.1

  Lipoproteins from Gram-positive and -negative bacteria, mycoplasma, and shorter synthetic lipopeptide analogues activate cells of the innate immune system via the Toll-like receptor TLR2/TLR1 or TLR2/TLR6 heterodimers. For this reason, these compounds constitute highly active adjuvants for vaccines either admixed or covalently linked. The lanthionine scaffold has structural similarity with the S-(2,3-dihydroxypropyl)cysteine core structure of the lipopeptides. Therefore, lanthionine-based lipopeptide amides were synthesized and probed for activity as potential TLR2 agonists or antagonists. A collection of analytically defined lipolanthionine peptide amides exhibited an inhibitory effect of the TLR2-mediated IL-8 secretion when applied in high molar excess to the agonistic synthetic lipopeptide Pam(3)Cys-Ser-(LyS)(4)-OH. Structure-activity relationships revealed the influence of the chirality of the two alpha-carbon atoms, the chain lengths of the attached fatty acids and fatty amines, and the oxidation level of the sulfur atom on the inhibitory activity of the lipolanthionine peptide amides.