マイクログラムの量から得られたジュラポリケチド由来スピロボラート色素の構造と絶対的構成
Klaus Wolkenstein1, Han Sun2, Heinz Falk3
1Department of Geobiology, Geoscience Centre, University of Göttingen , Goldschmidtstraße 3, 37077 Göttingen, Germany.
Journal of the American Chemical Society
|October 8, 2015
まとめ
研究者達は ジュラ紀の藻類から 古代のボロンを含んだ色素である ボロリトクロームの構造を明らかにした. これらの発見は古代と近代のポリケチドを結びつけ 自然産物の化学に関する 進化的洞察を明らかにしています
科学分野:
- 自然製品化学
- 古化学
- 有機化学
背景:
- 自然産物,特に古代代謝産物の構造の解明は,入手可能性と複雑性が限られているため,困難です.
- 古代の二次代謝物は 自然製品の進化史に洞察を与えます
- ボロンを含む天然製品は稀で,その進化的起源はよくわかっていない.
研究 の 目的:
- ジュラ紀の生物の謎の色素である ボロリトクロームの完全な構造と絶対的な構成を決定する
- 古代のボロン含有ピグメントの起源と進化の重要性を調査する.
- 古代代謝物質の分析におけるマイクロクリオプローブ NMR の有用性を実証する.
主な方法:
- 構造的決定のためのマイクロクリオプローブNMRスペクトロスコーピー
- 円形二重化スペクトロスコーピーは,絶対的な構成です.
- 構造的発見を支持する密度関数理論の計算.
主要な成果:
- ボロリトクロームの完全な構造と絶対的構成が解明され,特定のペンタサイクルのリガンドを持つスピロボラートとして明らかにされた.
- sec-ブチル群の構成は (S) として決定された.
- ジュラ紀のボロリトクロームと現代のポリケチドクロストルビンの間の構造的なリンクが確立され,共通の進化的起源と潜在的な細菌の産生を示唆した.
結論:
- ボロリトクロームは,最初に発見されたボロ酸性芳香性ポリケチドであり,既知のボロ酸性ポリケチドとは根本的に異なる.
- これらの発見は,これらの古代二次代謝物のほぼオリジナルの保存の証拠を提供します.
- この研究は,クロストルビン型ポリケチドの進化的意義と,古代生物分子の分析のためのマイクロクリオプローブNMRの可能性を強調しています.
さらに関連する動画
08:46Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
8.3K
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
3.6K
関連する概念動画
03:24Hybridization of Atomic Orbitals I
69.4K
The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
69.4K
02:34Structural Isomerism
22.4K
Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can...
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can...
22.4K
01:18Structure of Benzene: Molecular Orbital Model
13.8K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
13.8K
02:52Resonance
70.9K
The Lewis structure of a nitrite anion (NO2−) may actually be drawn in two different ways, distinguished by the locations of the N-O and N=O bonds.
70.9K
02:30Chirality at Nitrogen, Phosphorus, and Sulfur
7.4K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
7.4K
01:24π Molecular Orbitals of 1,3-Butadiene
12.7K
Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
12.7K