Boc-PheψLeu-OMe | 431063-61-5

• 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-PheψLeu-OMe
• 英文别名: Boc-Pheψ[CH(CN)NH]Leu-OMe；(S)-2-((S)-2-tert-Butoxycarbonylamino-1-cyano-3-phenyl-propylamino)-4-methyl-pentanoic acid methyl ester；methyl (2S)-2-[[(2S)-1-cyano-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropyl]amino]-4-methylpentanoate
• CAS: 431063-61-5
• 化学式: C₂₂H₃₃N₃O₄
• 分子量: 403.522
• InChiKey: PIKROJCNMNBVML-ADUPEVMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-PheψLeu-OMe 在 四丁基硫酸氢铵 sodium hydroxide 、 双氧水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (S)-2-((1S,2S)-2-Amino-1-carbamoyl-3-phenyl-propylamino)-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  A General Method for the Synthesis of Carbamoylmethyleneamino Pseudopeptides

  摘要：

  A general procedure for the preparation of (carbamoylmethylene)amino pseudopeptides from the corresponding (cyanomethylenene)amino analogues, compatible with peptide bonds and with the usual amino and carboxyl protecting groups, is described. This procedure involves the oxidative hydration of (cyanomethylene)amino pseudopeptides with basic hydrogen peroxide under phase-transfer conditions, using n-tetrabutylammonium hydrogen sulfate as catalyst. In the basic medium of this reaction the methyl esters of (carbamoylmethylene) amino pseudodipeptides cyclized to 2,6-dioxopiperazine analogues.

  DOI：

  10.1021/jo00092a019
• 作为产物：
  描述：

  三甲基氰硅烷 、 N-Boc-L-苯丙氨醛 、 L-亮氨酸甲酯盐酸盐 在 三乙胺 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 Boc-PheψLeu-OMe
  参考文献：
  名称：

  Ψ[CH（CN）NH]假肽的合成。新的肽键替代

  摘要：

  在存在的情况下，通过路易斯酸催化的N保护的α-氨基醛与C保护的氨基酸或肽的反应，一种简单而通用的通用方法来制备新的肽键替代物（[CH（CN）NH]描述了TMSCN的专利。

  DOI：

  10.1016/0040-4039(91)80539-i

文献信息

• 2-Oxopiperazine-Based γ-Turn Conformationally Constrained Peptides:  Synthesis of CCK-4 Analogues
  作者：Susana Herrero、M. Teresa García-López、Miriam Latorre、Edurne Cenarruzabeitia、Joaquín Del Río、Rosario Herranz

  DOI：10.1021/jo0256336

  日期：2002.5.1

  gamma-turn conformationally constrained tripeptides. The synthetic pathway devised for the preparation of both epimers of 1 at C(5) involves a reductive amination of cyanomethyleneamino pseudopeptides with amino acid derivatives, followed by regiospecific lactamization of the resulting C-backbone branched pseudopeptides. The versatility of this methodology is illustrated in the synthesis of analogues of the

  2-氧代哌嗪衍生物1已被设计为γ-转构象约束的三肽的模拟物。为在C（5）上制备两个差向异构体而设计的合成途径涉及用氨基酸衍生物对氰基亚甲基氨基假肽进行还原胺化，然后对所得C-骨架支链假肽进行区域特异性内酰胺化。四肽Boc- [Nle（31）]-CCK-4和Boc- [Lys（邻甲苯基氨基羰基）（31）]-CCK-4的类似物的合成说明了该方法的多功能性。在这些Boc-CCK-4类似物中引入新的构象限制，导致对CCK受体的亲和力损失2或3个数量级。这些结果表明CCK-4 C端三肽的生物活性构象中没有伽马转。
• C-Backbone branched peptides via reductive amination of cyanomethyleneamino pseudopeptides
  作者：Susana Herrero、M.Luisa Suárez-Gea、M.Teresa Garcı́a-López、Rosario Herranz

  DOI：10.1016/s0040-4039(02)00012-6

  日期：2002.2

  The synthesis of branched peptides from cyanomethylenamino pseudopeptides, via catalytic hydrogenation in the presence of amino acid derivatives, is described. When the inserted amino acid was a glycine derivative, the resulting branched peptide lactamized in situ to 2-oxopiperazine derivatives. This new C-backbone peptide branching approach is compatible with the diversity of amino acid side chains

  描述了由氰基亚甲基氨基伪肽通过在氨基酸衍生物存在下的催化氢化合成支链肽。当插入的氨基酸是甘氨酸衍生物时，所得的支链肽原位内酰胺化为2-氧代哌嗪衍生物。这种新的C骨干肽分支方法与氨基酸侧链的多样性兼容。
• Synthesis of Ψ[CH(CN)NH] pseudopeptides. A new peptide bond surrogate
  作者：Rosario Herranz、M.Luisa Suárez-Gea、Soledad Vinuesa、M.Teresa García-López、Ana Martínez

  DOI：10.1016/0040-4039(91)80539-i

  日期：1991.12

  An easy and versatile general method for the preparation of the new peptide bond surrogate Ψ[CH(CN)NH], by the Lewis acid catalyzed reaction of N-protected α-amino aldehydes with a C-protected amino acid or peptide in the presence of TMSCN, is described.

  在存在的情况下，通过路易斯酸催化的N保护的α-氨基醛与C保护的氨基酸或肽的反应，一种简单而通用的通用方法来制备新的肽键替代物（[CH（CN）NH]描述了TMSCN的专利。
• Branched peptides and conformationally constrained analogues from cyanomethyleneamino pseudopeptides
  作者：M. Luisa Suárez-Gea、M. Teresa García-López、Rosario González-Muñiz、Susana Herrero、Rosario Herranz

  DOI：10.1016/0040-4039(96)00198-0

  日期：1996.3

  Catalytic hydrogenation of cyanomethyleneamino pseudopeptides, followed by peptide coupling and cyclization of the resulting aminomethyleneamino intermediates, gives access to branched and conformationally constrained peptide analogues.

  氰基亚甲基氨基假肽的催化加氢反应，然后进行肽偶联和所得氨基亚甲基氨基中间体的环化，可得到分支的且构象受限的肽类似物。
• A General Method for the Synthesis of Carbamoylmethyleneamino Pseudopeptides
  作者：M. Luisa Suarez-Gea、M. Teresa Garcia Lopez、Rosario Herranz

  DOI：10.1021/jo00092a019

  日期：1994.7

  A general procedure for the preparation of (carbamoylmethylene)amino pseudopeptides from the corresponding (cyanomethylenene)amino analogues, compatible with peptide bonds and with the usual amino and carboxyl protecting groups, is described. This procedure involves the oxidative hydration of (cyanomethylene)amino pseudopeptides with basic hydrogen peroxide under phase-transfer conditions, using n-tetrabutylammonium hydrogen sulfate as catalyst. In the basic medium of this reaction the methyl esters of (carbamoylmethylene) amino pseudodipeptides cyclized to 2,6-dioxopiperazine analogues.