Boc-NH(Bzl)(D)Ala | 214262-82-5

• 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-NH(Bzl)(D)Ala
• 英文别名: (R)-(-)-Nα-benzyl-Nβ-Boc-(D)-hydrazinoalaniner；Boc-α-h(Bn)D-Ala-OH；(2R)-2-[benzyl-[(2-methylpropan-2-yl)oxycarbonylamino]amino]propanoic Acid
• CAS: 214262-82-5
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: VGRRUKULDYLAHI-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-NH(Bzl)(D)Ala 在 N-甲基吗啉 、 氯化亚砜 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 Boc-L-Leu-α-h(Bn)D-Ala-OMe
  参考文献：
  名称：

  一个有利的和手性α-hydrazinoesters的短合成：合成和1构象分析：1 [α/α- Ñ α -肼基]聚体

  摘要：

  经由S N 2协议已大规模获得具有高光学纯度的不同α-肼基酯。1 [α/α-：具有天然氨基酸通向相应二聚体，已经在为了得到1被低聚甲偶联反应Ñ α -肼基]聚体系列。构象研究表明，无论手性碳的绝对构型如何，这些混合的低聚物都是通过连续的γ转变和肼基转变在溶液中自组织的。

  DOI：

  10.1016/j.tet.2012.04.018
• 作为产物：
  描述：

  (R)-(-)-Nα-benzyl-Nβ-Boc-(D)-hydrazinoalanine methyl ester 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以98%的产率得到Boc-NH(Bzl)(D)Ala
  参考文献：
  名称：

  一个有利的和手性α-hydrazinoesters的短合成：合成和1构象分析：1 [α/α- Ñ α -肼基]聚体

  摘要：

  经由S N 2协议已大规模获得具有高光学纯度的不同α-肼基酯。1 [α/α-：具有天然氨基酸通向相应二聚体，已经在为了得到1被低聚甲偶联反应Ñ α -肼基]聚体系列。构象研究表明，无论手性碳的绝对构型如何，这些混合的低聚物都是通过连续的γ转变和肼基转变在溶液中自组织的。

  DOI：

  10.1016/j.tet.2012.04.018

文献信息

• Synthesis and Conformational Analysis of 1:1 [α/α-<i>N</i> ^α -Bn-Hydrazino] and 1:1 [α-<i>N</i> ^α -Bn-Hydrazino/α] Trimers: Determination of the Δ<i>δ</i> Value for the γ-Turn Structuration
  作者：Eugénie Romero、Ralph-Olivier Moussodia、Brigitte Jamart-Grégoire、Samir Acherar

  DOI：10.1002/ejoc.201800755

  日期：2018.9.16

  The conformational behavior of 1:1 [α/α‐Nα‐Bn‐hydrazino] and 1:1 [α‐Nα‐Bn‐hydrazino/α] oligomeric (dimer and/or trimer) pseudopeptides in CDCl3 has been studied by 1H NMR and IR spectroscopy. This study has highlighted the self‐organization of the oligomers by an alternation of the γ‐turn and hydrazinoturn and allowed the Δδ value for the γ‐turn structuration to be calculated for the first time.

  的1构象的行为：1 [α/α- Ñ α -Bn-肼基]和1：1 [α- Ñ α -Bn肼/α]低聚（二聚物和/或三聚体）在CDCl假肽3已经研究由1 H NMR和IR光谱。本研究由γ转角和hydrazinoturn的交替突出的低聚物的自组织和允许的Δ δ首次被计算为γ-转弯结构化值。
• Design and Synthesis of Hydrazinopeptides and Their Evaluation as Human Leukocyte Elastase Inhibitors
  作者：Laure Guy、Joëlle Vidal、André Collet、Augustin Amour、Michèle Reboud-Ravaux

  DOI：10.1021/jm980419o

  日期：1998.11.1

  The name hydrazinopeptide designates peptidic structures in which one of the native CONH links is replaced by a CONHNH (hydrazido) fragment. In this paper, we report the synthesis of such hydrazinohexapeptides (3-5) analogous to Z-Ala-Ala-Pro-Val-Ala-Ala-(NHPr)-Pr-i (6), a substrate of human leukocyte elastase (HLE; EC 3.4.21.37), cleaved by this serine protease between the Val4 and Ala5 residues. In hydrazinopeptides 3-5, the Ala5, Val4, or Pro3 residue, respectively, of the model peptide, has been replaced by the corresponding alpha-L-hydrazino acid. In 3, the bond likely to be cleaved by HLE is the one involving the CONHNH link, while in 4 and 5, this link is normally shifted away by one or two amino acid units from the catalytic serine. On incubation with HLE, hydrazinopeptide 3 proved to be a substrate and was cleaved between Val4 and NHAla5, like peptide 6. In contrast, 4 and 5 proved to bind to HLE without being cleaved, featuring properties consistent with reversible competitive inhibition. General guidelines for the synthesis of hydrazinopeptides are also reported in this paper. These guidelines take into account the chemical specificity of hydrazino acids, while being fully compatible with the conventional peptide coupling techniques. The utilization of orthogonally bisprotected hydrazino acids 1 where the N-beta and N-alpha atoms bear a Boc and a Bzl group, respectively, is recommended for the easy construction of such hydrazinopeptides.
• An expedient and short synthesis of chiral α-hydrazinoesters: synthesis and conformational analysis of 1:1 [α/α-Nα-hydrazino]mers
  作者：Ralph-Olivier Moussodia、Samir Acherar、Andrea Bordessa、Régis Vanderesse、Brigitte Jamart-Grégoire

  DOI：10.1016/j.tet.2012.04.018

  日期：2012.6

  Different α-hydrazinoesters with high optical purity have been obtained in large scale via an SN2 protocol. A coupling reaction with a natural amino acid leads to the corresponding dimers, which have been oligomerized in order to obtain the 1:1 [α/α-Nα-hydrazino]mer series. Conformational studies show that these mixed oligomers are self-organized in solution via a succession of γ-turn and hydrazinoturn

  经由S N 2协议已大规模获得具有高光学纯度的不同α-肼基酯。1 [α/α-：具有天然氨基酸通向相应二聚体，已经在为了得到1被低聚甲偶联反应Ñ α -肼基]聚体系列。构象研究表明，无论手性碳的绝对构型如何，这些混合的低聚物都是通过连续的γ转变和肼基转变在溶液中自组织的。