Organic chemistry of0life - uniurb.it · Organic chemistry of life.ppt Author: giovanni Created...
Transcript of Organic chemistry of0life - uniurb.it · Organic chemistry of life.ppt Author: giovanni Created...
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Organicchemistryof life
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Life begins with nucleic acidsThere are five heterocyclic bases in DNA and RNA
• There are only two purine bases found in nucleic acids: adenine (A), which we havealready met, and guanine (G)• The three pyrimidine bases are simpler: uracil (U), thymine (T), and cytosine (C).Cytosine is found in DNA and RNA, uracil in RNA only, and thymine in DNA only.
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The s>mulants in tea and coffee are methylated purines
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Nucleic acids exist in a double helix
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HIV and AIDS are treated with modified nucleosides
Cyclic nucleosides and stereochemistry
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Proteins are made of amino acids
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Amino acids combine to form pep>des and proteins
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Structural proteins must be tough and flexible
An>obio>cs exploit the special chemistry of bacteria
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Drugs based on pep>des or pep>domime>cs
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Sugars—just energy sources?
Sugars normally exist in cyclic forms with much stereochemistry
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Sugars can be fixed in one shape by acetal forma>on
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Glycosides in nature
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Glycosides in nature
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Most sugars are embedded in complexcarbohydrates
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Amino sugars add versa>lity to saccharides
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Lipids
Oil and water do not mix
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Mechanisms in biological chemistry
Nature’s NaBH4 is a nucleo>de: NADH or NADPH
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Nature’s NaBH4 is a nucleo>de: NADH or NADPH
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Reduc>ve amina>on in nature
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Nature’s enolate equivalents: lysine enamines and coenzyme A
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Phosphoenolpyruvate
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The shikimic acid pathway
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Natural products
Alkaloids are made by amino acid metabolism
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Pyrrolidine alkaloids are made from the amino acid ornithine
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Pyrrolidine alkaloids are made from the amino acid ornithine
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Benzyl isoquinoline alkaloids are made from tyrosine
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Benzyl isoquinoline alkaloids are made from tyrosine
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FaVy acids and other polyke>des are made from acetyl CoA
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FaVy acids and other polyke>des are made from acetyl CoA
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What is so important about unsaturated faVy acids?
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Aroma>c polyke>des
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Terpenes are vola>le cons>tuents of plants
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Terpenes are vola>le cons>tuents of plants
The steroids are another group of compounds derived from mevalonic acid. Theyinclude sex hormones such as testosterone and progesterone, and the cholesterolneeded to build cell membranes but also implicated in the damage to arteriescaused by atherosclerosis.