Cbz-(NMe)Phe-NH2 | 17191-53-6

• 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: Cbz-(NMe)Phe-NH2
• 英文别名: N^α-Benzyloxycarbonyl-N^α-methyl-Phe-amid；benzyl N-[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]-N-methylcarbamate
• CAS: 17191-53-6
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: RWXUWUUZJUJQJG-INIZCTEOSA-N

物化性质

• 沸点：
  519.8±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.63
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Cbz-(NMe)Phe-NH2 在 劳森试剂 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl N-[(2S)-1-amino-3-phenyl-1-sulfanylidenepropan-2-yl]-N-methylcarbamate
  参考文献：
  名称：

  Synthesis of the marine natural product barbamide

  摘要：

  报道了三氯化天然产物barbamide的首次全合成。该合成方法通过将(S)-3-三氯甲基丁酰氯与Meldrum酸（2,2-二甲基-1,3-二氧杂环己烷-4,6-二酮）偶联得到15，然后加入新型仲胺N-甲基-(S)-dolaphenine 2（从N-Cbz-L-苯丙氨酸经过6步反应，总产率为24%），得到β-酮酰胺16，随后直接转化为所需的(E)-烯醇醚。

  DOI：

  10.1039/b106087m
• 作为产物：
  描述：

  N-Cbz-N-甲基-L-苯丙氨酸甲酯 在 lithium hydroxide 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 生成 Cbz-(NMe)Phe-NH2
  参考文献：
  名称：

  Synthesis of the marine natural product barbamide

  摘要：

  报道了三氯化天然产物barbamide的首次全合成。该合成方法通过将(S)-3-三氯甲基丁酰氯与Meldrum酸（2,2-二甲基-1,3-二氧杂环己烷-4,6-二酮）偶联得到15，然后加入新型仲胺N-甲基-(S)-dolaphenine 2（从N-Cbz-L-苯丙氨酸经过6步反应，总产率为24%），得到β-酮酰胺16，随后直接转化为所需的(E)-烯醇醚。

  DOI：

  10.1039/b106087m

文献信息

• Polypeptides. Part VII. Variations of the phenylalanyl position in the C-terminal tetrapeptide amide sequence of the gastrins
  作者：H. Gregory、D. S. Jones、J. S. Morley

  DOI：10.1039/j39680000531

  日期：——

  The synthesis is described of analogues of L-tryptophyl-L-methionyl-L-aspartyl-L-phenylalanine amide (the C-terminal sequence of the gastrins) or its N-benzyloxycarbonyl, -t-butoxycarbonyl, or -carbamoyl derivatives wherein the phenylalanyl residue has undergone replacement by other naturally occuring amino-acyl residues or by αα-disubstituted amino-acyl residues, or has been modified by (a) substitution

  描述了L-色氨酸-L-甲硫酰基-L-天冬氨酰-L-苯丙氨酸酰胺（胃泌素的C-末端序列）或其N-苄氧羰基，-叔丁氧羰基或-氨基甲酰基衍生物的类似物的合成。苯丙氨酰基残基已被其他天然存在的氨基酰基残基或αα-二取代的氨基酰基残基取代，或已通过（a）在对位取代芳环进行修饰，（b）芳环的氢化，（c）亚氨基从α-碳原子转换为β-碳原子，（d）将苯环从β-碳原子转换为α-碳原子，（e）取代β-碳原子上的羟基，或（f）亚氨基的甲基化。
• Chiral Ligands Containing Heteroatoms; 9.¹General Procedures for the Synthesis of Optically Active 1-(2-Pyridyl)alkylamines from α-Amino Acids
  作者：Massimo Falorni、Giorgio Chelucci、Sandra Conti、Giampaolo Giacomelli

  DOI：10.1055/s-1992-26282

  日期：——

  General syntheses of 1-(2-pyridyl)alkylamines and N-methyl or N,N-dimethyl-1-(2-pyridyl)alkylamines from optically active α-amino acids are described. The presented procedures are based on catalyzed co-cyclotrimerization of the suitable nitriles with acetylene which can be conducted without loss of optical purity.

  介绍了从光学活性 δ± 氨基酸合成 1-(2-吡啶基)烷基胺和 N-甲基或 N,N-二甲基-1-(2-吡啶基)烷基胺的一般方法。所介绍的程序基于合适的腈与乙炔的催化共环三聚反应，可以在不损失光学纯度的情况下进行。
• Development of potent and selective CCK-A receptor agonists from Boc-CCK-4: tetrapeptides containing Lys(N.epsilon.)-amide residues
  作者：Kazumi Shiosaki、Chun Wel Lin、Hana Kopecka、Richard A. Craig、Bruce R. Bianchi、Thomas R. Miller、David G. Witte、Michael Stashko、Alex M. Nadzan

  DOI：10.1021/jm00089a010

  日期：1992.5

  A series of Boc-CCK-4 derivatives represented by the general structure Boc-Trp-Lys(N(epsilon)-COR)-Asp-Phe-NH2, where R is an aromatic, heterocyclic, or aliphatic group, are potent and selective CCK-AT receptor agonists. These amide-bearing compounds complement the previously described urea-based tetrapeptides (Shiosaki et al. J. Med. Chem. 1991, 34, 2837-2842); structure-activity studies revealed parallel as well as divergent trends between these two series. A significant correlation was observed between pancreatic binding affinity and the resonance constant R of the phenyl substituent in one particular series of derivatives. Sulfation of phenolic amides appended onto the epsilon-amino group of the lysine did not affect affinity for the CCK-AT receptor in contrast to the 500-fold increase in binding potency observed upon sulfation of CCK-8, suggesting that the lysine appendage and the sulfated tyrosine in CCK-8, both key structural elements that impart high affinity for the CCK-A receptor, are interacting differently with the receptor. The amide-bearing tetrapeptides are full agonists relative to CCK-8 in stimulating pancreatic amylase release while being partial agonists in eliciting phosphoinositide (PI) hydrolysis. Both effects were blocked by selective CCK-A receptor antagonists.