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The Kiliani-Fischer synthesis is a pivotal reaction in organic chemistry, crucial for the elongation of monosaccharide chains. Named after Heinrich Kiliani and Hermann Emil Fischer, it involves the addition of hydrogen cyanide to aldose sugars, forming cyanohydrins. This process introduces new chiral centers, resulting in diastereomers and enabling the synthesis of important biological molecules like nucleosides and various glycosides. Despite challenges such as racemization and selectivity, advancements in methodology continue to enhance its efficiency and selectivity.
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The Kiliani-Fischer synthesis is a chemical reaction used to increase the carbon chain length of monosaccharides
Chemists Heinrich Kiliani and Hermann Emil Fischer
The Kiliani-Fischer synthesis is named after chemists Heinrich Kiliani and Hermann Emil Fischer
The Kiliani-Fischer synthesis is essential in the field of carbohydrate chemistry for the synthesis of complex carbohydrates
The Kiliani-Fischer synthesis involves the addition of hydrogen cyanide to an aldose sugar to form a cyanohydrin intermediate
Formation of a Cyanohydrin Intermediate
The cyanohydrin intermediate is formed through the hydrolysis of the nitrile group in the Kiliani-Fischer synthesis
Reduction of the Intermediate
The intermediate in the Kiliani-Fischer synthesis is reduced to form a new stereocenter and extend the carbon chain
The Kiliani-Fischer synthesis results in a mixture of two diastereomers due to the introduction of a new chiral center
The Kiliani-Fischer synthesis is widely used for the elongation of aldose sugars in the synthesis of complex carbohydrates
Nucleosides
The Kiliani-Fischer synthesis is instrumental in the production of nucleosides, essential components of DNA and RNA
Glycosides
The Kiliani-Fischer synthesis is used to synthesize various glycosides found in bioactive natural products
The Kiliani-Fischer synthesis enables the construction of complex carbohydrates from simpler ones, playing a critical role in biochemistry and molecular biology
Recent advancements have improved the efficiency and selectivity of the Kiliani-Fischer synthesis, including the use of biocatalysts and green chemistry principles
Formation of Racemic Mixtures
The Kiliani-Fischer synthesis can result in racemic mixtures, limiting the yield of the desired enantiomer
Limited Selectivity
The Kiliani-Fischer synthesis has limited selectivity, making it challenging to synthesize larger carbohydrates
Despite its limitations, the Kiliani-Fischer synthesis remains a vital technique in organic chemistry, fostering further scientific discoveries and understanding of molecular structures
00
The ______-______ synthesis is crucial for extending the carbon chain of the simplest sugars, monosaccharides.
Kiliani-Fischer
01
In the ______-______ synthesis, hydrogen cyanide is added to an aldose sugar, resulting in a mixture of 'D' and 'L' sugar forms.
Kiliani-Fischer
02
Initial step in Kiliani-Fischer synthesis
Conversion of aldose sugar to aldonic acid via mild oxidation.
