#chirality

Chirality in Nature: From DNA to Snail Shells

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Introduction Chirality, derived from the Greek word for “hand,” is a property of asymmetry that is ubiquitous in nature. Just as our hands are mirror images but not identical, many biological molecules exhibit this fascinating characteristic. Chirality is not just a molecular curiosity; it profoundly influences the structure and function of DNA, proteins, and enzymes, as well as various physiological and behavioral traits in plants and animals. In this blog, we will explore the role …

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Molecular Handedness: How Chirality Shapes Molecules

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Introduction Molecules can come in two shapes that mirror each other, in the same way as our left and right hands. This attribute, called chirality, can be found in biological molecules like sugars and proteins This property, often referred to as molecular handedness, plays a crucial role in chemistry, biology, and pharmacology. In this article, we will explore the basics of chirality, examine examples of chiral and achiral molecules, and delve into the methods used to …

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Introduction to Chirality: Understanding the Basics

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Lead Chirality, derived from the Greek word “cheir” meaning hand, is a fundamental concept in chemistry that describes an object’s property of being non-superimposable on its mirror image. This property is not just an abstract mathematical idea but has profound implications in various scientific fields, particularly chemistry and biology. Understanding chirality is essential for comprehending molecular interactions and their impacts on our daily lives. This first of this blog series delves into the definition, historical …

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Harnessing JMP’s Prediction Profiler for Multi-Response Optimization of HPLC Method in Chiral Drug Separation

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Synopsis The development of chromatographic methods for the separation of chiral drugs presents a significant challenge, necessitating a comprehensive understanding of the compounds’ chemical properties and the factors influencing their separation. This task is further complicated by the presence of process-related impurities that can disrupt the separation process and compromise the quality of the results. However, the application of advanced statistical tools such as JMP’s Design of Experiments (DoE) and Prediction Profiler can significantly streamline …

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Rediscovery of stereochemistry

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Stereochemistry, in particular chirality, is known to us as early as 1809, when Malus, Arago and Biot discovered plane polarized light and its characteristics. It is observed that during 1950s to the 1970s, the “Golden Age” of drug discovery & development, stereochemistry was largely ignored resulting in approximately 57% of pharmaceuticals being marketed as racemates by the 1980s. Before going further let us examine the stereospecific awareness level that existed during 1980s’. Stereospecific Awareness level  …

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Levamisole

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Levamisole is used as anthelmintic agent to get rid of the intestinal worms. It is (S)-(-)-enantiomer of tetramisole. This drug is used in veterinary to treat hookworm infections.  Levamisole also finds therapeutic application in the treatment of colon cancer when given in conjunction with fluorouracil.   Chirality and biological activity Tetramisole carries one chiral stereogenic center and exists as an enantiomeric pair. The anthelmintic activity resides in the (S)-(-)-enantiomer, levamisole. The (R)- isomer harbors undesirable …

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Beta-Blockers

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Beta blockers, also spelled β-blockers, used as antihypertensive agents (lowering blood pressure), represent a class of chiral drugs that are marketed as racemates since the distomer exhibits no undesirable adverse effects. Three most important β-blockers viz. propranolol, atenolol, and metoprolol are marketed as racemic mixture. Chirality and biological activity β-blockers are aryloxy propanolamines with one stereogenic center and exists as a pair of enantiomers. It is observed that their therapeutic effect resides entirely in the (S)-enantiomer …

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L-Dopa

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Levodopa, L-Dopa, belong to a class of medications called dopamine agonists.  L-Dopa is used to increase dopamine concentrations in the treatment of  Parkinson’s disease. Most commonly, clinicians use levodopa as a dopamine replacement agent for the treatment of Parkinson disease. L-dopa is the precursor to dopamine and crosses the blood-brain barrier to increase dopamine neurotransmission. Chirality and Biological activity L-dopa, the (S)-enantiomer, is a chiral drug with one stereogenic center. It exists as a pair of enantiomers. The initial use …

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Terodiline

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(±)-Terodiline, the antianginal agent, perhaps represents the best authenticated example of a drug that had to be withdrawn from the world market as consequence of proven stereospecific toxicity. Terodiline has a close similarity to prenylamine from a structural and pharmacological view point. It was firs marketed as an antianginal agent but it exhibited urinary retention as a frequent and worrying side-effect. It was decided to exploit the the side-effect. Therefore the drug was redeveloped and …

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Prenylamine

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(±)-Prenylamine, an antianginal agent, was introduced in the market since early 1960. Reports associating Prenylamine with prolongation of the QT interval, ventricular tachycardia, and ventricular fibrillation started to appear. Some of these events had a fatal outcome and the drug was withdrawn from the market world-wide in 1988.  Chirality and drug withdrawals Prenylamine is chemically diphenyl-propyl derivative of phenylalkylamine. The drug is optically active with one stereogenic center (indicated by a red arrows), giving rise …

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