プサマプリシンA,M,O,QとセラチナミドAの総合成
Andrew P Morrow1, Myles W Smith1
1UT Southwestern Medical Center, 5323 Harry Hines Blvd., Dallas, Texas 75390, United States.
Journal of the American Chemical Society
|January 22, 2024
まとめ
研究者たちは新しいサイクル添加法を使って プサマプリスンと呼ばれる海洋アルカロイドを合成しました この研究は5つのpsammaplysinファミリーへのアクセスを提供し, (-) -psammaplysin Aの絶対的な構成を確認します.
科学分野:
- 海洋自然産物の化学
- 有機合成
- 薬剤化学
背景:
- プサマプリスンは 独特の類のブローミングされた海洋アルカロイドです
- これらの化合物は,チラミン由来ユニットに関連した特徴的な5/7-スピロイソキサゾリン-オキシペインコアを特徴としています.
研究 の 目的:
- いくつかのpsammaplysinファミリーの全合成を報告する.
- (-) -psammaplysin Aの最初の非対称合成を達成し,その絶対的構成を確認します.
主な方法:
- 定位で生成されたニトリル酸化物と7基のエネディオールジースの二極循環加減反応を用いた.
- 機能化されたスパイロサイクルの形成のために酸化変換を使用した.
- チラミン由来アミンと直接結合している.
- 非対称な合成のための適用された運動解像度.
主要な成果:
- 代表的なpsammaplysinファミリーの5つのメンバー:psammaplysins A,M,O,Q,およびセラチナミドAを成功裏に合成しました.
- (-) -psammaplysin Aの最初の非対称合成を達成しました.
- (-) プサマプリシンAの絶対構成を確認しました
結論:
- 開発された合成戦略は,プサマプリシンアルカロイドに効率的なアクセスを提供します.
- この合成により 海洋自然産物化学の理解が進んでいます
- 非対称合成は,鍵となる化合物の絶対的構成を検証する.
関連する概念動画
Carboxylic 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:
Structure of Amines
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
Glycosaminoglycans
Glycosaminoglycans (GAGs), also known as mucopolysaccharides, are long and linear polymers comprising of specific repeating disaccharides - the amino sugar that can be N-acetylglucosamine or N-acetylgalactosamine, and a uronic acid that is usually glucuronic acid or iduronic acid.
GAGS are found in the extracellular matrix of vertebrates, invertebrates, and bacteria. Due to their polar nature they attract water, and serve as excellent lubricants or shock absorbers in an animal body.
Hyaluronic...
GAGS are found in the extracellular matrix of vertebrates, invertebrates, and bacteria. Due to their polar nature they attract water, and serve as excellent lubricants or shock absorbers in an animal body.
Hyaluronic...
Composition of Polyprotic Acid Solutions as a Function of pH
Polyprotic acids of the type H2M constitute two ionizable protons. As a result, on titration with a base, they exhibit two equivalence points in the titration curve. During titration, the species H2M, HM−, and M2− will be present in the solution at different points. The fractions of H2M, HM−, and M2− present at the various instances of the titration are denoted by α0, α1, and α2, respectively.
A graph with the alpha values is plotted against the volume of base added during titration. Here, a...
A graph with the alpha values is plotted against the volume of base added during titration. Here, a...
Peptidoglycan Synthesis
Structure of PeptidoglycanPeptidoglycan is a vital structural component of the bacterial cell wall, providing mechanical strength and shape to the cell. It consists of repeating units of two sugars—N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM)—linked by β-1,4 glycosidic bonds. These sugar chains are cross-linked by short peptide chains, forming a mesh-like polymer that surrounds the bacterial plasma membrane.Cytoplasmic Phase – Precursor SynthesisPeptidoglycan biosynthesis begins in...
Sulfur Assimilation
Sulfur is an essential element in biological systems, contributing to synthesizing key biomolecules, including amino acids such as cysteine and methionine, and cofactors such as coenzyme A and biotin. Microorganisms primarily assimilate sulfur as sulfate (SO₄²⁻) from the environment, which must undergo a series of biochemical transformations before it can be incorporated into cellular components. As sulfate is highly oxidized, it must undergo assimilatory sulfate reduction to become...


