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Chirality in Nature02:30

Chirality in Nature

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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
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Directly Acting Muscle Relaxants: Dantrolene and Botulinum Toxin01:26

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This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
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A racemic mixture, or racemate, is an equimolar mixture of enantiomers of a molecule that can be separated using their unique interaction with chiral molecules or media. Racemic mixtures are denoted by the (±)- prefix. This ‘optical rotation descriptor’ applies to the whole solution of a racemic mixture rather than a specific stereoisomer. Enantiomers typically have the same physical and chemical properties. Hence, they are not easily separable. However, enantiomers can exhibit...
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A High Content Imaging Assay for Identification of Botulinum Neurotoxin Inhibitors
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バトラコトキシンの非対称合成:エナティオメア毒素は,NaVに対する機能的差異を示している.

Matthew M Logan1, Tatsuya Toma1, Rhiannon Thomas-Tran1

  • 1Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA.

Science (New York, N.Y.)
|November 19, 2016
PubMed
まとめ

研究者らはバトラキトキシンエナントイオマーを合成し,非自然な (+) 形態が,天然のアゴニストとは異なり,電圧ゲートナトリウムチャネル (NaV) 反抗体として作用することを発見した. これは共有された結合部位とNaVダイナミクスを調節する新しい方法を示しています.

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Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
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科学分野:

  • 神経科学と薬理学
  • 有機化学と化学生物学

背景:

  • (-) バトラホトキシン (Batrachotoxin) はステロイド性神経毒素で,電圧ゲートナトリウムチャネル (NaVs) を強力に活性化する.
  • バトラコトキシンの構造-活性関係を理解することは,NaV機能の調節剤の開発に不可欠です.

研究 の 目的:

  • 自然 (-) と非自然 (+) のバトラコトキシンの両方の簡潔な非対称合成を達成する.
  • C-20ベンゾアート改変バトラキシン誘導体のエナンチオマーを合成する.
  • これらの合成された分子のNaVサブタイプにおける機能的活動を調査し,それらの結合部位を特定する.

主な方法:

  • バトラコトキシンとその誘導体の非対称合成
  • 様々なNaVサブタイプで合成された化合物の電気生理学的特徴付け.
  • NaVチャネル内の結合部位を特定するためのタンパク質変異.

主要な成果:

  • (-) と (+) バトラホトキシンエナントイオマーとそのC-20ベンゾ酸導体の合成に成功.
  • 非天然の (+) バトラキトキシンエナントイオメルは,天然の (-) - バトラキトキシンアゴニストとは異なるNaVチャネルの可逆性アンタゴニストとして機能する.
  • ミュタゲネーシスのデータは,NaVチャネルの内孔腔内の両エナントオメアの共通の結合部位を示唆する.

結論:

  • バトラコトキシンの反対のエナティオメアは,対極のチャネル活性を示し,NaVsとのステレオスペシフィックな相互作用を強調する.
  • NaVの内孔にある共通の結合部位は,アゴニストとアンタゴニストの両方のエナンチオメールを収容する.
  • これらの発見は,チャネルダイナミクスを調節するためにNaVの内孔をターゲットとする新しい小分子設計の基礎を提供します.