1-07-09 Nucleic acid structure + intro SET 1

Nucleic - Section I(with clinical correlates Nucleic Acid Exists in Two Fundamental Chemical Forms DNA = Deoxyribonucleic acid RNA = Ribonucleic

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Section I (with clinical correlates)
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Nucleic Acid Exists in Two Fundamental Chemical Forms D NA = D eoxyribon ucleic a cid R NA = R ibon ucleic a cid Nucleic acids are Hetero polymers (cf. Proteins and carbohydrates) Building blocks of nucleic acids are MONO NUCLEOTIDES and high molecular weight nucleic acids are often referred to as Poly nucleotides (more later) Mononucleotides serve many other metabolic functions (more later) A mononucleotide has three components in a 1:1:N molar ratio (where N is an integer, usually from 1-3) Nitrogenous BASE Pentose SUGAR ORTHOPHOSPHATE IONS (as PHOSPHORYL groups) There are Several Functional Forms of Nucleic Acid DNA is for storage of genetic information in cellular organisms. RNA’s have several functions for gene expression
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N N N H N N N Pyrimidine Purine (Pyr) (Pur) 1 2 1 2 7 8 Imidazole ring Component 1: Base Heterocyclic Scaffolds of Bases and Numbering Recognize the Scaffolds and learn the Numbering system
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N H N H CH 3 O O N H N N N NH 2 2,4-dioxo, 5-methyl pyrimidine 6-amino purine = = or Thymine ( T ) Adenine ( A ) “Nucleobases” are Functionalized Purines or Pyrimidines Nucleobases are one component (building block) of Nucleic Acids. They: ● come in 5 flavors (T, A, G ,U and C) ● contain H-bond donor and accepting groups ● are conjugated unsaturated and therefore planar ● are relatively insoluble (esp. Purines) ● account largely for the heterogeneity in NA type. ● exist as tautomers – the lactam (keto) and amino forms shown predominate Learn the their chemical and trivial names Recognize the structures and tautomers Identify those typically found in D- and RNA
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N H N H O O COOH N H N N H N O 2,4-dioxo, 6-carboxy pyrimidine 6-oxo purine = = or or Orotate ( O ) Hypoxanthine ( Hx ) “Non-nucleobases” are Metabolic Intermediates These are rarely * components of Nucleic Acids but are intermediates in biosynthesis and degradation of the building blocks and other critical metabolites. (For our purposes), the non-nucleobase: ● comes in 5 flavors (O, Hx, X (xanthine), Dihydroorotate and Uric acid) purines are relatively insoluble (ie. Urate < X < Hx) Learn trivial names of the five nucleobases Recognize the structures. THINK about how nucleobase and non-nucloebase structure are related –this will help with metabolism (more later)
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N H N H O O F N H N N H N S 2,4-dioxo, 5-fluoro pyrimidine 6-mercapto purine = = or Flurouracil (5-FU) 6-MP or 5-flurouracil Base Analogs as Drugs Structurally-simple derivatives of bases are important drugs. The agents shown are: ● classified as antimetabolites ● first line treatments for certain cancers ☺ These and others (e.g. Allopurinol) will be covered during Recitation in terms of Mechanism of Action (MOA)and Clinical Use (more later).
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O OH OH O H OH O H OH O H OH Ribose 2-Deoxy ribose 1 2 3 4 5 Component 2: Pentose Sugar Nucleic Acid sugars and numbering Sugars are another component (building block) of Nucleic Acids.
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This note was uploaded on 03/22/2009 for the course PHCY 422 taught by Professor Bastow during the Spring '09 term at UNC.

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Nucleic - Section I(with clinical correlates Nucleic Acid Exists in Two Fundamental Chemical Forms DNA = Deoxyribonucleic acid RNA = Ribonucleic

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