Kiliani Fischer Synthesis

Embark on an in-depth journey into the realm of Kiliani Fischer Synthesis - a vital procedure within the boundaries of organic chemistry. This comprehensive exploration grants detailed insights into the definition, role, and mechanistic process, as well as the advantages, disadvantages, and real-world applications of Kiliani Fischer Synthesis. Understand its significance in carbohydrate synthesis and learn about the benefits and limitations it presents in laboratory and industrial settings. Lastly, delve into the variations on the process and advances made in the techniques of this critical chemical reaction.

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Table of contents

    Understanding Kiliani Fischer Synthesis

    Kiliani Fischer Synthesis is a key concept you'll encounter in your studies of organic chemistry. It centres around carbohydrates and monosaccharides—important tasks you'll often see in biochemistry and molecular biology.

    The Kiliani-Fischer Synthesis, named after its discoverers Heinrich Kiliani and Emil Fischer, is a traditional laboratory method for the synthesis of monosaccharides. Specifically, monosaccharides with greater numbers of carbon atoms.

    Definition of Kiliani Fischer Synthesis

    In essence, Kiliani Fischer Synthesis is a method used to elongate carbon chains in monosaccharides. The technique involves two primary steps:
    • Adding cyanide to the carbohydrate to extend the chain.
    • Reducing the newly added cyanide to an alcohol, which forms a new stereocenter.
    This process is significantly useful because it is stereospecific. That's a term you'll often hear in organic chemistry – it refers to a reaction that can give different stereoisomers depending on the stereochemistry of the reactant. Here's a simple summary of the process in a table:
    Addition of cyanide to carbohydrate Creation of a new nitrile functionality
    Reduction of cyanide to alcohol Formation of a new stereocenter

    Role of Kiliani Fischer Synthesis in Organic Chemistry

    Kiliani Fischer Synthesis plays an important role in preparing and altering monosaccharides, which are crucial components of many bioactive substances and natural products. Because the method alters the stereochemistry of the carbohydrate, it can be used to synthesize both 'D' and 'L' stereoisomers of sugars.

    Consider D-erythrose. By using the Kiliani-Fischer Synthesis method, you can extend the carbon chain of D-erythrose to form D-ribose and D-arabinose, two sugars that are incredibly important in biochemistry: D-ribose forms the backbone of RNA, and D-arabinose is a component of many bioactive natural products.

    While Kiliani Fischer Synthesis is an instrumental technique for synthesizing sugars, it's important to note that it produces a mixture of 'D' and 'L' sugars. This is because it creates a new stereocenter with no control over the stereochemistry.

    You might be wondering why having control over stereochemistry is important in the first place. Well, different stereoisomers (like 'D' and 'L' sugars) can have different physical properties and biological activities. In biochemistry and drug discovery, it's often necessary to have pure stereoisomers rather than a mixture because even small differences in stereochemistry can dramatically affect a substance's properties.

    In eliminating the shortcomings of Kiliani Fischer Synthesis, biochemists have sought alternative methods to do stereocontrolled carbohydrate synthesis. Still, understanding the basics of Kiliani Fischer Synthesis is an essential foundation for anyone studying organic chemistry.

    The Kiliani Fischer Synthesis Process

    The Kiliani Fischer Synthesis Process is an intriguing aspect of chemistry, involving chemical reactions that revolve around organic compounds. More specifically, this synthesis facilitates the conversion of an aldose to a larger aldose, that is, a carbohydrate with more carbon atoms.

    Step-by-step Breakdown of Kiliani Fischer Synthesis Mechanism

    In discussing the process of the Kiliani Fischer Synthesis Mechanism, a step-by-step approach indeed helps to demystify its mechanics. Here is a comprehensive breakdown:
    Step 1: Oxidation
    Step 2: Cyanohydrin Formation
    Step 3: Hydrolysis
    Step 4: Reduction
    In the first step, oxidation occurs. The aldose is oxidised to an aldonic acid. This step involves the conversion of the aldehyde functionality \( \text{R-CHO} \) to a carboxylic acid functionality \( \text{R-COOH} \). A common reagent used for this conversion is nitric acid \( \text{HNO}_{3} \). The second step involves cyanohydrin formation. Here, the aldonic acid reacts with hydrocyanic acid \( \text{HCN} \), forming a cyanohydrin. Cyanohydrin is an organic compound containing a hydroxy and cyano group. Notably, the \( \text{CN}- \) group attaches to the carbon atom in the place of the removed hydroxyl \( \text{OH}- \) group during this process, resulting in an increase in the total carbon count. Then comes the third stage, hydrolysis. The cyanohydrin undergoes this process, converting the \( \text{CN}- \) group to a \( \text{COOH}- \) group, thus forming an aldonic acid but with an extended chain. In the fourth and final step, reduction takes place. The aldonic acid is reduced to yield a mixture of aldoses. This process involves the mild reduction of the carboxylic acid functionality back to an aldehyde functionality. Typically, reagents like \( \text{NaBH}_{4} \) or \( \text{LiAlH}_{4} \) are used in this process.
           OH  O                OH  O                         OH  O
         HC     C             HC     C                      HC     C
           HO CH                      HO CH                       HO CH
         HC     C             HC     C                      HC     C
           |                     |                              |
           H                     CN              --->            COOH
           -                     -                              -
       D-Glucose          Cyanohydrin          Oxidized to form Aldonic acid
    Overall, Kiliani Fischer Synthesis serves as an exceptional procedure to lengthen carbohydrates, enabling the creation of more complex organic molecules. As with all chemistry processes, understanding each step and the chemical reactions involved is key to gaining in-depth knowledge about this Synthesis Mechanism.

    Application of Kiliani Fischer Synthesis

    Kiliani Fischer Synthesis finds its application predominantly in the arena of carbohydrate chemistry. This process offers a controlled way to elongate the carbon chain in an aldose monosaccharide, forming a larger carbohydrate. The process creates an additional asymmetric carbon atom, bringing along an increased complexity. It thereby allows for the possibility of creating an array of products from a relatively simpler monosaccharide.

    Use of Kiliani Fischer Synthesis in Carbohydrate Synthesis

    Carbohydrate synthesis has always been a complex branch of organic chemistry due to the plethora of isomers that even a simple carbohydrate can have. Kiliani Fischer Synthesis offers valuable support in this intricate field. Diving deeper into the details, monosaccharides are extremely important carbohydrates. They serve as energy sources and also act as building blocks for complex carbohydrates. But the diversity and complexity of carbohydrates present in nature surpasses the few monosaccharides attainable conveniently through extraction from natural sources. This is where Kiliani Fischer Synthesis steps in. It provides a method of extending the carbon chain of carbohydrates systematically. Through this method, it's possible to create a new carbon, thus forming more complex carbohydrates from simpler ones. Here's a glimpse of the reactions that take place in the Kiliani Fischer Synthesis:
    Oxidation of aldose\(RCHO \rightarrow RCOOH\)
    Cyanohydrin Formation\(RCOOH + HCN \rightarrow RCOOH_{C|N}/OH\)
    Hydrolysis\(RCOOH_{C|N}/OH \rightarrow RCOOH_{C|OH}/OH\)
    Reduction\(RCOOH_{C|OH}/OH \rightarrow RCH_{2}OH_{C|OH}/OH\)
    These series of reactions, when meticulously controlled, can extend the carbon chain in a monosaccharide. This process not only achieves controlled growth but also forms a new stereocenter. Note that the term 'stereocenter' here refers to the carbon atom bonded to four different groups, making it asymmetric. However, it is important to consider the limitations of the synthesis. The method creates a new stereocenter with no control over the stereochemistry, therefore producing a racemic mixture of D and L isomers.

    Real-world Kiliani Fischer Synthesis Examples

    While the realm of theoretical learning is essential, often knowing the practical application drives the concept home. In the real world, Kiliani Fischer Synthesis has been pivotal to the growth of biochemistry and molecular biology. Take Deoxyribonucleic Acid (DNA), for instance. It is molecules that contain your genetic code, and every single living organism on the planet possesses it. The backbone structure of these vital molecules comprised pended sugar molecules, the synthesis of which can be traced back to Kiliani Fischer Synthesis. Let's consider D-ribose, an essential component of Ribonucleic Acid (RNA) and various other biochemical molecules. Its synthesis from D-erythrose is facilitated by the Kiliani Fischer synthesis method.
    Kiliani Fischer Synthesis
    Similarly, D-arabinose, another sugar of significant importance in bioactive compounds, can be synthesized from the same D-erythrose compound through this same process. Hence, extending the fundamental understanding of chemistry, these real-world examples highlight the use and significance of the Kiliani Fischer Synthesis. An understanding of this process is, therefore, fundamental not just to mastering organic chemistry but also carving corners in the broader scientific milieu.

    Advantages and Disadvantages of Kiliani Fischer Synthesis

    In order to understand the utility of the Kiliani Fischer Synthesis, it's important to delve into both its advantages and drawbacks. By exploring the benefits and limitations of this intricate process, you can better grasp its vital importance in chemistry and its inherent restrictions.

    Potential Benefits of Kiliani Fischer Synthesis

    Undeniably, the Kiliani Fischer Synthesis signifies an influential organic reaction, capable of transforming simpler carbohydrates into their larger versions. The process not only acknowledges the creation of more complex carbohydrates but also furthers our step towards making new compounds. Let's consider some of the potential benefits of this process:
    • Systematic synthesis of more complex carbohydrates: This process has made the conversion of simpler carbohydrates into more complex ones a systematic concept, allowing chemists to manipulate the size of aldoses with relative ease.
    • Advancement in carbohydrate chemistry: Kiliani Fischer Synthesis serves as a rudimentary tool in elucidating carbohydrate structures. It not only paved the way for understanding structural differences in isomers but also offered insights into the intricate stereochemistry associated with carbohydrates.
    • Scope in biochemistry and molecular biology: The synthesis has marked its importance in medical chemistry. Kiliani Fischer Synthesis has the potential to fabricate bioactive compounds and naturally occurring products like nucleosides and glycosides, thereby opening new dimensions in research.
    In terms of chemical reactions, the formation of cyanohydrin marks the elongation process. This reaction essentially introduces an extra carbon atom into the molecule. \[ \text{RCHO} + \text{HCN} \rightarrow \text{RCH(OH)CN} \] The subsequent steps, including hydrolysis and reduction, finalise the process, resulting in an aldose with an extra carbon atom.

    Concerns and Limitations of Kiliani Fischer Synthesis

    Notwithstanding its significant benefits, the Kiliani Fischer Synthesis also has certain limitations and concerns, which are important to consider for a comprehensive understanding of the process. Firstly, one primary limitation of the Kiliani-Fischer synthesis is that it results in a combination of epimers. This process lacks the ability to control over one of the newly formed stereogenic centres, thereby yielding a mix of enantiomers. Thus, this process does not offer a chemically efficient path to either of the larger sugars, but rather a mixture. Here are the issues to be considered:
    Creation of a mixture of epimersThe process cannot control the stereochemistry at the new stereogenic center. As a result, both D and L isomers are produced in equal amounts.
    Lack of selectivityThe reaction cannot selectively produce either of the D or L sugars, presenting a lack of control over the product.
    Inefficient yieldAlso, as both D and L sugar molecules are synthesised, obtaining a high yield of a single desired product is challenging.
    Furthermore, the process is not efficient in creating large carbohydrates. That's because with each step, an increased number of isomers are created. Additionally, the increase in carbon atom leads to the formation of new asymmetric carbon atoms, resulting in even more isomers. Moreover, the reduction reaction of the \( \text{RCH(OH)CN} \) to a carbonyl group is not highly selective, contributing to a lower yield of the desired product.
           | Reductive Conversion
      CHO (Desired product) + COH (Unwanted product)
    Consequently, while the Kiliani Fischer Synthesis signifies a crucial step in science and holds potential for creating complex bioactive molecules, its limitations pose hindrances and challenges to chemists and researchers. An understanding of these limitations is vital to working towards innovative solutions and modifications to this process, potentially leading to more effective synthesis techniques in future.

    Delving into Kiliani Fischer Synthesis

    To further comprehend the Kiliani Fischer Synthesis process, we must first break it down into its components. The method involves a series of carefully controlled chemical reactions that result in the systematic enlargement of the carbon chain of a given carbohydrate, specifically, an aldose. Here, it becomes clear there is no restriction in using D or L-aldoses. It's the nature of the reaction that lends itself to providing a full range of carbohydrates from simple ones. Yes, despite the increased complexity, it is a manageable process, and understanding its intricacies can provide a wealth of opportunities in the related scientific sphere.

    Variations of the Kiliani Fischer Synthesis Process

    Now, let's delve deeper into the actual variations in the Kiliani Fischer Synthesis procedure. There are a few changes possible in the overall process, whether it's in the starting aldose or the subsequent steps of reaction. As a result, an array of products is possible as the reaction does not restrict its ability to just increasing one carbon atom at a time. Want to add more? That's also possible, albeit a more laboured and careful process. However, in this age of scientific progress, changing up the structure is assuredly not out of bounds. There isn't necessarily a "one size fits all" formula for a Kiliani Fischer Synthesis; thus, variations arise from differing methodologies. These variations may include alternate reactions to the given path, different precursor molecules, or adjustments in the environment where the reaction is performed. Let's throw light on the typical stages of Kiliani Fischer Synthesis, represented through elementary variations:
     D-aldose or L-aldose 
           | Oxidation
     D/L-aldonic acid
           | Reaction with HCN
     D/L-aldonic acid cyanohydrin
           | Hydrolysis
     D/L-aldonic acid amide
           | Reduction (using NaBH4 or H2 with a catalyst)
     Two D-and L-aldoses with one more carbon atom than the starting material
    The preliminary step involves the oxidation of the aldehyde \( \text{RCHO} \rightarrow \text{RCOOH} \). Then, the synthesized aldonic acid reacts with hydrogen cyanide to yield aldonic acid cyanohydrin. The following stage involves hydrolysis of the freshly formed nitrile, forming an amide, which is lastly reduced to form a mixture of two aldoses that have one carbon atom more than the initial aldose. While these steps can be replicated in most laboratories with relative ease, the process is not devoid of challenges. The formation of by-products during the reactions is one of the problems faced. The fact that the process fails to selectively lead to one stereoisomer directly is also a considerable limitation. This signifies that the reaction is not enantioselective, forming an obstinate challenge in carbohydrate chemistry.

    Advances in Kiliani Fischer Synthesis Techniques

    The scientific world is dynamic and ever-evolving, and the domain of Kiliani Fischer Synthesis is no exception. Over the years, multiple advances have been made to refine this process and overcome the inherent limitations. While the original methodology remains a fundamental mainstay in carbohydrate chemistry, subsequent scientific advances have contributed to more efficient methods to synthesise carbohydrates with larger carbon chains selectively. These enhancements have predominantly revolved around optimisation of the reaction environment, warehousing of intermediary products and enhancement of the process's enantioselectivity. In terms of optimisation of the reaction environment, novel technologies such as the use of sonic energy have been sourced as potential tools to catalyse the chemical reaction, so it takes less time and ensure that the process is more efficient. Moreover, the scientific community is recognising the significance of "green chemistry," which seeks to minimise the environmental impact of chemical reactions. As such, eco-friendly alternatives to the harsh reducing agents typically used in Kiliani Fischer Synthesis have also surfaced. Interfaces of Kiliani Fischer Synthesis with biocatalytic processes represent another growing field. For instance, ideas hitched on enzyme-catalysed cyanohydrin formations have risen in recent years. A promising study detailed the enzyme-based formation of optically active cyanohydrins, which is a significant step toward asymmetric synthesis, successfully bypassing the racemic mixture produced in traditional Kiliani Fischer Synthesis. Additionally, modifications in the systematic extraction and warehousing of intermediaries have given way to isolation procedures that minimise impurities in the final carbohydrate product, heralding significant improvements.


    Despite its limitations, the profound legacy of Kiliani Fischer Synthesis remains undisturbed. Its role in biosynthetic applications, such as nucleotide synthesis, cannot be downplayed. With modern modifications and enhancements surfacing every day, Kiliani Fischer Synthesis continues to reign as a cornerstone of carbohydrate chemistry and provides fertile ground for the continuous evolution and development of the scientific world.

    Kiliani Fischer Synthesis - Key takeaways

    • Definition of Kiliani Fischer Synthesis: A chemical process allowing the conversion of an aldose to a larger aldose, meaning a carbohydrate with more carbon atoms.
    • Kiliani Fischer Synthesis process: Broken down into four main steps - oxidation, cyanohydrin formation, hydrolysis, and reduction. This series of reactions facilitate the lengthening of carbohydrates.
    • Application of Kiliani Fischer Synthesis: Predominantly used in carbohydrate chemistry for elongating the carbon chain in an aldose monosaccharide and creating additional asymmetric carbon atoms, thus increasing the complexity.
    • Kiliani Fischer Synthesis examples: Used in real-world contexts, including the synthesis of D-ribose and D-arabinose from D-erythrose. It is also fundamental for advancing organic chemistry, biochemistry, and molecular biology.
    • Advantages and disadvantages of Kiliani Fischer Synthesis: While it presents an important method for creating more complex carbohydrates and understanding their structures, it produces a racemic mixture of D and L isomers due to uncontrolled stereochemistry. It also has low efficiency for producing large carbohydrates.
    Kiliani Fischer Synthesis Kiliani Fischer Synthesis
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    Frequently Asked Questions about Kiliani Fischer Synthesis
    What are the products of Kiliani-Fischer Synthesis? Write in UK English.
    The products of Kiliani-Fischer synthesis are two different monosaccharides, differing in their stereochemistry at one carbon atom. These monosaccharides are higher homologues of the original carbohydrate.
    What is Kiliani-Fischer Synthesis? Write in UK English.
    Kiliani-Fischer Synthesis is a chemistry procedure used to extend an aldose by one carbon atom, essentially resulting in a pair of epimeric sugars. It involves oxidation of an aldose into an aldonic acid, followed by cyanohydrin formation, and hydrolysis to form the new aldose and its epimer.
    How is Kiliani-Fischer Synthesis used?
    Kiliani-Fischer Synthesis is used in the field of organic chemistry to synthesise carbohydrates, specifically, it's utilised to extend the carbon chain of aldoses, producing a pair of diastereomeric sugars in equal proportion.
    How will you synthesise glucose from arabinose?
    To synthesise glucose from arabinose in Kiliani-Fischer synthesis, first arabinose is oxidised to arabinonic acid followed by cyanohydrin formation. This compound is then hydrolysed triggering Aldol condensation, which elongates the carbon chain. Finally, it is reduced to form glucose.
    What is an example of Kiliani-Fischer Synthesis? Please write in UK English.
    An example of Kiliani-Fischer Synthesis is the process used to convert d-glucose into d-mannose and d-galactose, where cyanohydrin formation and subsequent stereoselective reduction is performed.

    Test your knowledge with multiple choice flashcards

    What are the main limitations of the traditional Kiliani Fischer Synthesis process?

    What is the Kiliani Fischer Synthesis Process?

    How does Kiliani Fischer Synthesis contribute to carbohydrate synthesis?


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