Boc-Lys(Trt)-OH | 139200-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Boc-Lys(Trt)-OH
• 英文别名: (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(tritylamino)hexanoic acid
• CAS: 139200-47-8
• 化学式: C₃₀H₃₆N₂O₄
• 分子量: 488.627
• InChiKey: DCTJAZANZMDEJH-SANMLTNESA-N

物化性质

• 沸点：
  643.4±55.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.66
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-叔丁氧羰基-N'-甲苯磺酰基-L-精氨酸 、 Boc-Tyr(Br-Z)-OH 、 Boc-Tyr(Br-Z)-Asp-OPac 、 Boc-Lys(Trt)-OH 生成 cyclo^1,5Boc-Lys-Arg(Tos)-Tyr(Br-Z)-Tyr(Br-Z)-Asp-OPac 、
  参考文献：
  名称：

  Probing the functional conformation of neuropeptide Y through the design and study of cyclic analogs

  摘要：

  The functional importance of the PP-fold conformation in neuropeptide Y (NPY) was investigated. NPY and N(alpha)-Ac-NPY(10-36), and corresponding cyclic analogues cyclo18,22-[Lys18,Asp22]-NPY and N(alpha)-Ac-cyclo18,22-[Lys18,Asp22]-NPY(10-36), were synthesized. Strategies for synthesis of the cyclic analogues included the use of the Kaiser oxime resin and a segment condensation approach. Circular dichroism studies in phosphate buffer, pH 5.0, indicated self-association of all four peptides at low micromolar concentrations. Monomeric N(alpha)-Ac-NPY(10-36) showed only 13% alpha-helix, compared to 32% alpha-helix for monomeric NPY, demonstrating a helix-stabilizing effect of residues 1-9 that is consistent with the PP fold. The [Lys18,Lys22] lactam bridge stabilized the helical conformation in N(alpha)-Ac-NPY(10-36) (51% alpha-helix), but was helix destabilizing in NPY (21% alpha-helix). In rat brain receptor binding assays, the cyclic and linear N(alpha)-Ac-NPY(10-36) analogues were equipotent (IC50 = 13 nM for I-125-BH-NPY displacement), although the cyclic analogue was twice as potent in rat vas deferens assays. NPY was more potent than its cyclic analogue in the brain receptor binding assays (IC50 = 0.07 and 0.25 nM, respectively), but these peptides were equipotent in the vas deferens assays. These results support a functional role for the PP fold in NPY and correlate with the solution conformations of the monomeric peptides.

  DOI：

  10.1021/jm00084a021
• 作为产物：
  描述：

  Boc-Lys-OMe acetate 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 17.25h， 生成 Boc-Lys(Trt)-OH
  参考文献：
  名称：

  Probing the functional conformation of neuropeptide Y through the design and study of cyclic analogs

  摘要：

  The functional importance of the PP-fold conformation in neuropeptide Y (NPY) was investigated. NPY and N(alpha)-Ac-NPY(10-36), and corresponding cyclic analogues cyclo18,22-[Lys18,Asp22]-NPY and N(alpha)-Ac-cyclo18,22-[Lys18,Asp22]-NPY(10-36), were synthesized. Strategies for synthesis of the cyclic analogues included the use of the Kaiser oxime resin and a segment condensation approach. Circular dichroism studies in phosphate buffer, pH 5.0, indicated self-association of all four peptides at low micromolar concentrations. Monomeric N(alpha)-Ac-NPY(10-36) showed only 13% alpha-helix, compared to 32% alpha-helix for monomeric NPY, demonstrating a helix-stabilizing effect of residues 1-9 that is consistent with the PP fold. The [Lys18,Lys22] lactam bridge stabilized the helical conformation in N(alpha)-Ac-NPY(10-36) (51% alpha-helix), but was helix destabilizing in NPY (21% alpha-helix). In rat brain receptor binding assays, the cyclic and linear N(alpha)-Ac-NPY(10-36) analogues were equipotent (IC50 = 13 nM for I-125-BH-NPY displacement), although the cyclic analogue was twice as potent in rat vas deferens assays. NPY was more potent than its cyclic analogue in the brain receptor binding assays (IC50 = 0.07 and 0.25 nM, respectively), but these peptides were equipotent in the vas deferens assays. These results support a functional role for the PP fold in NPY and correlate with the solution conformations of the monomeric peptides.

  DOI：

  10.1021/jm00084a021