Organic Chemistry Special Project

Organic Chemistry Special Project - Simple, High Yield...

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Simple, High Yield Methods for the Synthesis of Aldehydes Directly from o-, m-, and p- Carborane and Their Further Conversions. Santhosh Varadarajan Organic Chemistry Special Project
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In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These are the building blocks of proteins. They form short polymer chains called peptides or longer chains called either polypeptides or proteins through a condensation reaction. Humans can produce 10 of the 20 amino acids. The others must be supplied in the food. Failure to obtain enough of even 1 of the 10 essential amino acids, those that we cannot make, results in degradation of the body's proteins—muscle and so forth—to obtain the one amino acid that is needed. The 20 amino acids that are found within proteins convey a vast array of chemical versatility. Amino acids and proteins are essential to human life and research in this domain is imperative. Methods for introducing aldehyde functionalities into proteins have become central to protein engineering efforts. An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double-bonded to an oxygen atom (chemical formula O=CH-), is very important in organic chemistry. Oxygen is more electronegative than carbon which means it pulls the electrons in the carbon-oxygen bond towards itself, creating an electron deficiency at the carbon atom. Because of this the molecule is said to be polar and can be synthesized relatively easily and be put to use in many reactions. One significant reaction making use of this functional group is the oxidation of proteins by the enzyme myeloperoxidase, in the artery wall. This enzyme oxidizes tyrosine to tyrosyl radical
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using hydrogen peroxide as an oxidizing agent. Myelperoxidase forms the aldehyde p- hydroxyphenylacetaldehyde (pHA), in the process of oxidizing L-Tyrosine. An aldehyde serves as an excellent building block in synthetic chemistry. They are very versatile in the sense that they can be reduced into a primary alcohol (-CH2OH), or oxidized into a carboxylic acid (-COOH). Each of these two groups is also very beneficial in synthesis chemistry. One of the main reactions aldehydes are good for is a nucleophilic addition reaction. The resonance structure of an aldehyde gives a positive charge on the central carbon and a minus charge on the oxygen. This makes it possible for a nucleophile to add to the central carbon forming a stable tetrahedral geometry. The resulting structure is a negatively charged oxygen, a hydrogen, nucleophile and an arbitrary group attached to a central carbon. One of the many examples or this reaction is the Grignard Reaction. The general form of this reaction is shown below.
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The R group on an aldehyde has a major effect on how it will react with compounds under certain conditions. In a biological sense this R group can be an amino acid or protein. This reaction happens all the time in our bodies with proteins and poly
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This note was uploaded on 11/02/2009 for the course CHM 263 taught by Professor Grutzner during the Spring '09 term at Purdue University-West Lafayette.

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Organic Chemistry Special Project - Simple, High Yield...

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