N-(tert-butoxycarbonyl)-D-methionyl-L-leucine methyl ester | 82611-46-9

• 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: N-(tert-butoxycarbonyl)-D-methionyl-L-leucine methyl ester
• 英文别名: Boc-D-Met-Leu methyl ester；Boc-D-Met-Leu-OCH3；methyl (2S)-4-methyl-2-[[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-methylsulfanylbutanoyl]amino]pentanoate
• CAS: 82611-46-9
• 化学式: C₁₇H₃₂N₂O₅S
• 分子量: 376.517
• InChiKey: YDAPZLXQYTXIPR-OLZOCXBDSA-N

物化性质

• 沸点：
  524.7±50.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-D-methionyl-L-leucine methyl ester 在 sodium hydroxide 、 sodium hydride 、 N,N'-二环己基碳二亚胺 、 碘甲烷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.75h， 生成 L-lysyl-L-α-aspartyl-L-seryl-L-phenylalanyl-L-valyl-(αS,3R)-3-amino-α-(2-methylpropyl)-2-oxo-1-pyrrolidineacetyl-L-methioninamide
  参考文献：
  名称：

  Conformationally constrained tachykinin analogs: potent and highly selective neurokinin NK-2 receptor agonists

  摘要：

  The design and synthesis of potent and seleCtive neurokinin NK-2 receptor agonists 12 (GR64349) and 31 are described, together with structure-activity relationships for related analogues. Compound 12 (EC50 = 3.7 nM at NK-2 receptors in the rat colon; selectivity > 1000- and > 300-fold with respect to NK-1 and NK-3 receptors. respectively) was derived by incorporation of a Gly-Leu gamma-lactam conformational constraint into the C-terminal region of the neurokinin A. octapeptide analogue [Lys3]-NKA(3-10). Compound 31 (EC50 = 15 nM in rat colon) contains a novel fused-bicyclic constraint at the corresponding site in the substance P hexapeptide analogue [Ava6]-SP(6-11).

  DOI：

  10.1021/jm00100a027
• 作为产物：
  描述：

  L-亮氨酸甲酯盐酸盐 、 N-Boc-D-蛋氨酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 生成 N-(tert-butoxycarbonyl)-D-methionyl-L-leucine methyl ester
  参考文献：
  名称：

  Cyclic peptides as selective tachykinin antagonists

  摘要：

  Twenty homodetic cyclic peptides based on the C-terminal sequence of substance P were prepared (Table I) by a combination of solid-phase techniques and cyclizations using azide coupling Incorporation of dipeptide mimics based on substituted gamma-lactams were used in some cases to restrict their conformational mobility. Five of these cyclic peptides were shown to have high tachykinin antagonist activity (pA2 > 6) at NK-2 receptors (rat vas deferens). The two most potent of this series, XVII, cyclo(Gln-Trp-Phe-Gly-Leu-Met) (pA2 = 8.1), and I cyclo(Gln-Trp-Phe-(R)Gly[ANC-2]Leu-Met) (pA2 = 6.7), were selective for NK-2 receptors compared with the other tachykinin receptors (Table II).

  DOI：

  10.1021/jm00053a001

文献信息

• Analogs of substance P and eledoisin
  申请人：Merck & Co., Inc.

  公开号：US04680283A1

  公开（公告）日：1987-07-14

  Analogs of substance P and eledoisin which are conformationally constrained by the presence of a lactam in the peptide chain demonstrate greater selectivity and increased protease stability and are useful as analgesic, anti-inflammatory, antihypertensive, central nervous system agents, and stimulants of lachrymal secretion. The compounds are prepared by standard peptide synthetic procedures.

  被内酰胺所限制构象的物质P和eledoisin的类似物表现出更大的选择性和增强的蛋白酶稳定性，可用作镇痛剂、抗炎药、降压药、中枢神经系统剂和泪液分泌刺激剂。这些化合物是通过标准的肽合成程序制备的。
• VEBER, DANIEL F.;FREIDINGER, ROGER
  作者：VEBER, DANIEL F.、FREIDINGER, ROGER

  DOI：——

  日期：——