(2S)-2-amino-3-(9,10-dihydro-9-oxoacridin-2-yl)propanoic acid methyl ester | 643018-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (2S)-2-amino-3-(9,10-dihydro-9-oxoacridin-2-yl)propanoic acid methyl ester
• 英文别名: methyl (2S)-2-amino-3-(9-oxo-10H-acridin-2-yl)propanoate
• CAS: 643018-85-3
• 化学式: C₁₇H₁₆N₂O₃
• 分子量: 296.326
• InChiKey: OSBKRGPUGIWUGR-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-amino-3-(9,10-dihydro-9-oxoacridin-2-yl)propanoic acid methyl ester 在 水 、 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 18.0h， 生成 cyanomethyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(9-oxo-9,10-dihydroacridin-2-yl)propionate
  参考文献：
  名称：

  Tryptophan-based fluorophores for studying protein conformational changes

  摘要：

  With the continuing interest in deciphering the interplay between protein function and conformational changes, small fluorescence probes will be especially useful for tracking changes in the crowded protein interior space. Presently, we describe the potential utility of six unnatural amino acid fluorescence donors structurally related to tryptophan and show how they can be efficiently incorporated into a protein as fluorescence probes. We also examine the various photophysical properties of the new Trp analogues, which are significantly redshifted in their fluorescence spectra relative to tryptophan. In general, the Trp analogues were well tolerated when inserted into Escherichia coli DHFR, and did not perturb enzyme activity, although substitution for Trp22 did result in a diminution in DHFR activity. Further, it was demonstrated that D and E at position 37 formed efficient FRET pairs with acridon-2-ylalanine (Acd) at position 17. The same was also true for a DHFR construct containing E at position 79 and Acd at position 17. Together, these findings demonstrate that these tryptophan analogues can be introduced into DHFR with minimal disruption of function, and that they can be employed for the selective study of targeted conformational changes in proteins, even in the presence of unmodified tryptophans. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.015
• 作为产物：
  描述：

  Boc-4-氨基-L-苯丙氨酸 在 氯化亚砜 、 铜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (2S)-2-amino-3-(9,10-dihydro-9-oxoacridin-2-yl)propanoic acid methyl ester
  参考文献：
  名称：

  Tryptophan-based fluorophores for studying protein conformational changes

  摘要：

  With the continuing interest in deciphering the interplay between protein function and conformational changes, small fluorescence probes will be especially useful for tracking changes in the crowded protein interior space. Presently, we describe the potential utility of six unnatural amino acid fluorescence donors structurally related to tryptophan and show how they can be efficiently incorporated into a protein as fluorescence probes. We also examine the various photophysical properties of the new Trp analogues, which are significantly redshifted in their fluorescence spectra relative to tryptophan. In general, the Trp analogues were well tolerated when inserted into Escherichia coli DHFR, and did not perturb enzyme activity, although substitution for Trp22 did result in a diminution in DHFR activity. Further, it was demonstrated that D and E at position 37 formed efficient FRET pairs with acridon-2-ylalanine (Acd) at position 17. The same was also true for a DHFR construct containing E at position 79 and Acd at position 17. Together, these findings demonstrate that these tryptophan analogues can be introduced into DHFR with minimal disruption of function, and that they can be employed for the selective study of targeted conformational changes in proteins, even in the presence of unmodified tryptophans. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.015

文献信息

• Synthesis ofN-[(tert-Butoxy)carbonyl]-3-(9,10-dihydro-9-oxoacridin-2-yl)-L-alanine, a New Fluorescent Amino Acid Derivative
  作者：Aneta Szymańska、Katarzyna Wegner、Leszek Łankiewicz

  DOI：10.1002/hlca.200390275

  日期：2003.10

  A simple synthesis of a new, highly fluorescent amino acid and of its protected derivative useful in peptide studies is described. The obtained derivative, N-[(tert-butoxy)carbonyl]-3-(9,10-dihydro-9-oxoacridin-2-yl)-L-alanine (6), shows intense long-wave absorption (above 360 nm) and emission (above 400 nm). The quantum yield of fluorescence of the investigated compound is very high, so it can serve

  描述了一种新的，高度荧光的氨基酸及其在肽研究中有用的受保护衍生物的简单合成。所获得的衍生物N -[（叔丁氧基）羰基] -3-（9,10-二氢-9-氧杂cri啶-2-基）-L-丙氨酸（6）显示出强烈的长波吸收（360 nm以上） ）和发射（400 nm以上）。被研究化合物的荧光量子产率非常高，因此可以用作灵敏的分析探针，例如，用于分析肽构象。