関連する実験動画
Updated: Jul 15, 2026
11:44
Synthesis and Mass Spectrometry Analysis of Oligo-peptoids
Published on: February 21, 2018
O-ボラノフォスホペプチドとO-ディチオフォスホペプチドの固体相合成と生化学的研究
Kenneth E Jenkins1, Adrian P Higson, Peter H Seeberger
1Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
Journal of the American Chemical Society
|June 6, 2002
まとめ
新種のフォスフォペプチド模倣剤であるO-ボラノフォスフォペプチドとO-ディチオフォスフォペプチドは,安定性を高め,酵素を阻害します. これらのペプチドアナログは,細胞のプロセス制御のためのフォスフォタンパク質を模倣する.
科学分野:
- バイオケミストリー バイオケミストリー
- 有機化学 オーガニック・ケミストリー
- 分子生物学は分子生物学である.
背景:
- 信号伝達経路は,タンパク質のリン酸化により,成長や分化などの重要な細胞機能を調節する.
- フォスフォタンパク質を模倣する安定したペプチドアナログの開発は,これらのプロセスを in vitro および in vivo で制御するために不可欠です.
研究 の 目的:
- フォスフォペプチド模倣剤の2つの新しいクラス:O-ボラノフォスフォペプチドとO-ディチオフォスフォペプチドを合成し,特徴づけること.
- Yersinia protein tyrosine phosphatase (PTP) に対するこれらの新種のミミティックの抑制活性と酵素の安定性を評価する.
主な方法:
- 固相合成は,H-フォスフォナートおよびH-フォスフォノチオアートモノエステルを使用し,ベースラビルの9-フッ素メチル (Fmoc) 保護基を持つ.
- 合成には,濃縮が続いて,ボラン複合物 (ボラノフォスホペプチドの場合) または元素硫黄 (ディチオフォスホペプチドの場合) で酸化が伴う.
- 濃縮アンモニアム水酸化物を用いて,固体からの支えと保護を取り除く.
主要な成果:
- タイロシン,セリン,スレオニンから派生したO-ボラノフォスホペプチドとO-ディチオフォスホペプチドを成功して合成した.
- Ac-YIIPLPG-NH2 アナログはYersinia PTPを競争力を持って抑制し,KI値はそれぞれ430 ± 50 μMと670 ± 50 μMでした.
- 両方とも新しいフォスフォペプチドの類型であり,Yersinia PTPによる酵素性水解に対する耐性を示し,ディチオフォスフォペプチドは24時間以上完全に安定していた.
結論:
- O-ボラノフォスホペプチドとO-ディチオフォスホペプチドは,安定したフォスホプロテイン模倣物の新しいクラスを表しています.
- これらのアナログは,タンパク質のリン酸化を含む信号伝導経路の研究および調節のための貴重なツールとして機能することができます.
- 強化された安定性と阻害特性により,治療や研究用途の有望な候補となります.
さらに関連する動画
関連する概念動画
03:02Organic Compounds
All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
02:17What is Organic Chemistry?
Organic chemistry is the study of compounds of carbon called organic compounds. Organic compounds either originate from living organisms or are synthesized by chemists. A defining trait of these compounds is the presence of carbon as the principal element, which is bonded to other carbon atoms and other elements such as hydrogen, oxygen, nitrogen, and sulfur. The existence of a wide array of organic molecules is a consequence of carbon atoms’ ability to form up to four strong bonds to other...
01:28IR and UV–Vis Spectroscopy of Carboxylic Acids
In IR spectroscopy of carboxylic acids, the C=O bond shows a characteristic band between 1710 and 1760 cm⁻¹, and the O–H bond exhibits a broad band between 2500 and 3300 cm⁻¹.
However, the stretching absorptions for the C=O bond vary depending on the structure of carboxylic acids. The C=O bond of the free carboxylic acids shows a higher stretching frequency, 1760 cm−1, while H-bonded carboxylic acids (dimers) exhibit stretching absorptions at a lower frequency, 1710 cm−1. The C=O bond of the...
However, the stretching absorptions for the C=O bond vary depending on the structure of carboxylic acids. The C=O bond of the free carboxylic acids shows a higher stretching frequency, 1760 cm−1, while H-bonded carboxylic acids (dimers) exhibit stretching absorptions at a lower frequency, 1710 cm−1. The C=O bond of the...
01:15Carboxylic Acid Derivatives: Overview
Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:
01:28Structures of Carboxylic Acid Derivatives
Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
01:13Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.