BOC-DL-7-氮杂色氨酸 | 129423-33-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 色氨酸类衍生物
• 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
• 中文名称: BOC-DL-7-氮杂色氨酸
• 英文名称: N-(Boc)-D,L-7-azatryptophan
• 英文别名: D,L-N-t-Boc-azatryptophan；t-Boc-7-azatrp；N-t-Boc-D,L-7-azatryptophan；2-((tert-butoxycarbonyl)amino)-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid；2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid
• CAS: 129423-33-2
• 化学式: C₁₅H₁₉N₃O₄
• 分子量: 305.334
• InChiKey: FDLAXTKUGQAPTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  BOC-DL-7-氮杂色氨酸 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 S-phenethyl 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanethioate hydrochloride
  参考文献：
  名称：

  设计结核分枝杆菌CYP121抑制剂的底物片段化。

  摘要：

  必需的结核分枝杆菌（Mtb）酶CYP121的环二肽底物被解构成其组成片段并针对该酶进行筛选。鉴定了许多命中，其中之一表现出意想不到的抑制剂样结合模式。阐明了抑制药效基团，并通过以CYP121底物的结构为指导的合成加工，迅速提高了片段结合亲和力。所得抑制剂与其他Mtb P450相比，具有较低的微摩尔亲和力，良好的预测理化性质和对CYP121的选择性。抑制剂结合模式的光谱表征可深入了解弱氮供体配体对P450血红素的影响，

  DOI：

  10.1002/cmdc.201600248
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 DL-7-氮杂色氨酸 在 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.5h， 以72%的产率得到BOC-DL-7-氮杂色氨酸
  参考文献：
  名称：

  In Vitro Site-Specific Incorporation of Fluorescent Probes into β-Galactosidase

  摘要：

  Fluorescence spectroscopy is a powerful biophysical technique for studying protein structure, function, dynamics, and intermolecular interactions. Such studies are often conducted using intrinsic probes, such as tryptophan residues, or extrinsic probes introduced by post-translational modification, such as dansyl. Specificity, however, is often a concern since many proteins contain more than one tryptophan and chemical modification often will occur at more than one site. Herein we report the in vitro, site-specific incorporation of three fluorescent amino acid analogues, 5-hydroxytryptophan, 7-azatryptophan, and epsilon-dansyllysine, each of which was incorporated into beta-galactosidase at a single designated site.

  DOI：

  10.1021/ja963023f

文献信息

• Interaction of Enantiomers of Lysyl-7-Azatryptophyl-Lysine with Acidic Phospholipid Vesicles: A Fluorescence Study
  作者：J. D. Brennan、I. D. Clark、C. W. V. Hogue、A. S. Ito、L. Juliano、A. C. M. Paiva、B. Rajendran、A. G. Szabo

  DOI：10.1366/0003702953963210

  日期：1995.1

  A tripeptide containing a single 7-azatryptophan (7AW) residue was synthesized with the use of racemic 7AW and purified by high-performance liquid chromatography (HPLC). The peptide NH₂-lysyl-7-azatryptophyl-lysine (K7AWK) is analogous to the peptide lysine-tryptophyl-lysine (KWK) whose interactions with acidic lipids are well characterized. It has not been possible to achieve the separation of 7AW D and L enantiomers under HPLC conditions that normally are used to separate enantiomers of amino acids. HPLC of the peptide, however, indicated that there were two main components of nearly equal concentration in the partially purified synthetic peptides. Thin-layer chromatography, paper electrophoresis, amino acid analysis, and steady-state absorption and fluorescence spectra showed that the two HPLC peaks corresponded to peptides with the same composition but with different enantiomers of 7AW. Time-resolved fluorescence measurements of the purified enantiomers indicated that there were differences in the excited-state decay parameters. The nature of the interaction of the different enantiomers of the basic peptide with vesicles of the acidic lipid palmitoyl-oleoyl phosphatidylserine (POPS) at pH 5.0 has been elucidated with the use of steady-state fluorescence measurements. Interaction of the peptide with vesicles in the liquid crystalline phase suggested that proton transfer from the POPS to the 7AW occurs, resulting in enhanced emission at 450 nm. These results are compared to those from the Trp containing peptide KWK, and the unique advantages of 7AW as a spectroscopic probe are described.

  使用手性7-azatryptophan（7AW）残基合成了含有一种7-azatryptophan（7AW）残基的三肽，并通过高效液相色谱（HPLC）纯化。这个肽NH₂-lysyl-7-azatryptophyl-lysine（K7AWK）类似于肽赖氨酸-色氨酸-赖氨酸（KWK），其与酸性脂质的相互作用已经得到很好的表征。在通常用于分离氨基酸对映体的HPLC条件下，尚不可能实现7AW D和L对映体的分离。然而，对肽的HPLC分析表明，在部分纯化的合成肽中有两个主要成分，浓度几乎相等。薄层色谱、纸电泳、氨基酸分析以及稳态吸收和荧光光谱表明，这两个HPLC峰对应于具有相同组成但带有不同7AW对映体的肽。纯化对映体的时间分辨荧光测量表明，在激发态衰减参数方面存在差异。使用稳态荧光测量阐明了在pH 5.0下，不同对映体的基本肽与酸性脂质棕榈酰-油酰磷脂酰丝氨酸（POPS）囊泡的相互作用。肽与液晶相囊泡的相互作用表明，从POPS到7AW的质子转移发生，导致450 nm处的增强发射。这些结果与含色氨酸的肽KWK进行了比较，并描述了7AW作为光谱探针的独特优势。
• Synthesis and Photophysics of the Optical Probe N1-Methyl-7-azatryptophan
  作者：R. L. Rich、A. V. Smirnov、A. W. Schwabacher、J. W. Petrich

  DOI：10.1021/ja00153a005

  日期：1995.12

  The development of a new intrinsic optical probe of protein structure and dynamics, N-1-methyl-7-azatryptophan (1M7AT), is reported. The utility of this nonnatural amino acid derivative lies in its single-exponential, long-lived fluorescence decay (21.7 +/- 0.4 ns) and in its high fluorescence quantum yield (0.53 +/- 0.07). Its absorption and emission maxima are red-shifted 10 and 65 nm, respectively, from those of tryptophan. These characteristics permit its unambiguous detection with unprecedented discrimination against emission from multiply occurring native tryptophan residues. In a mixture of these two amino acids, no tryptophan signal is detected until the tryptophan: N-1-methyl-7-azatryptophan ratio exceeds 75:1. Consequently, N-1-methyl-7-azatryptophan is ideal for studying the interactions of small peptides containing it with large proteins.
• Substrate Fragmentation for the Design of<i>M. tuberculosis</i>CYP121 Inhibitors
  作者：Madeline E. Kavanagh、Janine L. Gray、Sophie H. Gilbert、Anthony G. Coyne、Kirsty J. McLean、Holly J. Davis、Andrew W. Munro、Chris Abell

  DOI：10.1002/cmdc.201600248

  日期：2016.9.6

  the structures of CYP121 substrates. The resulting inhibitors have low micromolar affinity, good predicted physicochemical properties and selectivity for CYP121 over other Mtb P450s. Spectroscopic characterisation of the inhibitors' binding mode provides insight into the effect of weak nitrogen-donor ligands on the P450 heme, an improved understanding of factors governing CYP121-ligand recognition and

  必需的结核分枝杆菌（Mtb）酶CYP121的环二肽底物被解构成其组成片段并针对该酶进行筛选。鉴定了许多命中，其中之一表现出意想不到的抑制剂样结合模式。阐明了抑制药效基团，并通过以CYP121底物的结构为指导的合成加工，迅速提高了片段结合亲和力。所得抑制剂与其他Mtb P450相比，具有较低的微摩尔亲和力，良好的预测理化性质和对CYP121的选择性。抑制剂结合模式的光谱表征可深入了解弱氮供体配体对P450血红素的影响，
• <i>In Vitro</i> Site-Specific Incorporation of Fluorescent Probes into β-Galactosidase
  作者：Lance E. Steward、Cynthia S. Collins、Marcella A. Gilmore、Justin E. Carlson、J. B. Alexander Ross、A. Richard Chamberlin

  DOI：10.1021/ja963023f

  日期：1997.1.1

  Fluorescence spectroscopy is a powerful biophysical technique for studying protein structure, function, dynamics, and intermolecular interactions. Such studies are often conducted using intrinsic probes, such as tryptophan residues, or extrinsic probes introduced by post-translational modification, such as dansyl. Specificity, however, is often a concern since many proteins contain more than one tryptophan and chemical modification often will occur at more than one site. Herein we report the in vitro, site-specific incorporation of three fluorescent amino acid analogues, 5-hydroxytryptophan, 7-azatryptophan, and epsilon-dansyllysine, each of which was incorporated into beta-galactosidase at a single designated site.