(5S)-5-tert-butoxycarbonylamino-4-oxo-hexanoic acid tert-butyl ester | 959513-50-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (5S)-5-tert-butoxycarbonylamino-4-oxo-hexanoic acid tert-butyl ester
• 英文别名: (S)-tert-butyl 4-oxo-5-(tert-butoxycarbonylamino)hexanoate；tert-butyl (5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxohexanoate
• CAS: 959513-50-9
• 化学式: C₁₅H₂₇NO₅
• 分子量: 301.383
• InChiKey: KRURIUCOTFZCPW-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S)-5-tert-butoxycarbonylamino-4-oxo-hexanoic acid tert-butyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-tert-butyl 4-oxo-5-acetylaminohexanoate
  参考文献：
  名称：

  Synthesis and antibacterial activity of alaremycin derivatives for the porphobilinogen synthase

  摘要：

  The preparation and the antibacterial activity of alaremycin derivatives such as their CF(3)-derivatives and (R)- and (S)-4-oxo-5-acetylaminohexanoic acid for the porphobilinogen synthase (PBGS), were described. The IC(50) values of the antibacterial activity of the prepared materials for the inhibitor of PBGS, were determined using PBGS assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.106
• 作为产物：
  描述：

  BOC-L-丙氨酸甲酯 在 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 12.0h， 生成 (5S)-5-tert-butoxycarbonylamino-4-oxo-hexanoic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and antibacterial activity of alaremycin derivatives for the porphobilinogen synthase

  摘要：

  The preparation and the antibacterial activity of alaremycin derivatives such as their CF(3)-derivatives and (R)- and (S)-4-oxo-5-acetylaminohexanoic acid for the porphobilinogen synthase (PBGS), were described. The IC(50) values of the antibacterial activity of the prepared materials for the inhibitor of PBGS, were determined using PBGS assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.106

文献信息

• Hydroxyethylene isosteres introduced in type II collagen fragments substantially alter the structure and dynamics of class II MHC A^q/glycopeptide complexes
  作者：Cecilia Lindgren、Ida E. Andersson、Lotta Berg、Doreen Dobritzsch、Changrong Ge、Sabrina Haag、Urszula Uciechowska、Rikard Holmdahl、Jan Kihlberg、Anna Linusson

  DOI：10.1039/c5ob00395d

  日期：——

  Introduction of hydroxyethylene isosteres into glycopeptides led to loss of Aq affinity and subsequent T cell response due to disruption of hydrogen bond networks.

  将羟基乙烯异构体引入糖肽中导致Aq亲和力的降低和后续T细胞反应的丧失，这是由于氢键网络的破坏所致。
• Probing Molecular Interactions within Class II MHC A^q/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis
  作者：Ida E. Andersson、Balik Dzhambazov、Rikard Holmdahl、Anna Linusson、Jan Kihlberg

  DOI：10.1021/jm0705410

  日期：2007.11.1

  T cells obtained in a mouse model for rheumatoid arthritis are activated by a glycopeptide fragment from rat type II collagen (CII) bound to the class II major histocompatibility complex A(q) molecule. We report a comparative model of A(q) in complex with the glycopeptide CII260-267. This model was used in a structure-based design approach where the amide bond between Ala(261) and Gly(262) in the glycopeptide was selected for replacement with psi[COCH2], psi[CH2NH2+], and psi[(E)-CH=CH] isosteres. Ala-Gly isostere building blocks were then synthesized and introduced in CII260-267 and CII259-273 glycopeptides. The modified glycopeptides were evaluated for binding to the A(q) molecule, and the results were interpreted in view of the A(q)/glycopeptide model. Moreover, recognition by a panel of T-cell hybridomas revealed high sensitivity for the backbone modifications. These studies contribute to the understanding of the interactions in the ternary A(q)/glycopeptide/T-cell receptor complexes that activate T cells in autoimmune arthritis and suggest possibilities for new vaccination approaches.
• Synthesis and antibacterial activity of alaremycin derivatives for the porphobilinogen synthase
  作者：Noritaka Iwai、Kyosuke Nakayama、Jumpei Oku、Tomoya Kitazume

  DOI：10.1016/j.bmcl.2011.03.106

  日期：2011.5

  The preparation and the antibacterial activity of alaremycin derivatives such as their CF(3)-derivatives and (R)- and (S)-4-oxo-5-acetylaminohexanoic acid for the porphobilinogen synthase (PBGS), were described. The IC(50) values of the antibacterial activity of the prepared materials for the inhibitor of PBGS, were determined using PBGS assay. (C) 2011 Elsevier Ltd. All rights reserved.