Advanced Biochemistry and Chemical Biology CHM4034 Spring 2008

1. Advanced Biochemistry and Chemical BiologyCHM4034 Spring 2008 • Dr. Lyons office hours lyons@chem.ufl.edu 846-3392 • W 10-11 AM • T,R 4:00-5:00 PM Class website http://www.chem.ufl.edu/~lyons/

2. Monosaccharides are modified

3. Monosaccharides are modified

4. Oxidation reduction reactions : The aldehyde moiety in aldoses can be oxidize to yield a carboxylic acid, the resulting compounds are known as aldonic acids. Aldose Aldonic Acid Uronic Acid Glucose Gluconic Acid Glucuronic Acid

5. Monosaccharides are modified

6. - The reduction of the carbonyl group in aldoses and ketoses yields polyols known as alditols Ribitol Ribose

7. Inositol Glycerol

8. Nucleic Acids The Ultimate Building Blocks

11. Purines Adenosine monophosphate NUCLEOTIDE Adenine BASE Deoxyadenosine monophosphate DEOXYNUCLEOTIDE Deoxyadenosine DEOXYNUCLEOSIDE Adenosine NUCLEOSIDE

12. Purines Guanosine monophosphate NUCLEOTIDE Guanine BASE Deoxyguanosine monophosphate DEOXYNUCLEOTIDE Deoxyguanosine DEOXYNUCLEOSIDE Guanosine NUCLEOSIDE

13. Pyrimidines Cytidine monophosphate NUCLEOTIDE Cytosine BASE Deoxycytidine monophosphate DEOXYNUCLEOTIDE Deoxycytidine DEOXYNUCLEOSIDE Cytidine NUCLEOSIDE

14. Pyrimidines (DNA only) Thymidine monophosphate NUCLEOTIDE Thymine BASE Deoxythymidine monophosphate DEOXYNUCLEOTIDE Deoxythymidine DEOXYNUCLEOSIDE Thymidine NUCLEOSIDE

15. Pyrimidines (RNA only) Uracil BASE Uridine Monophosphate NUCLEOTIDE Uridine NUCLEOSIDE

16. AMP/dAMP Nucleotide monphosphate ADP/dADP Nucleotide diphosphate ATP/dATP Nucleotide triphosphate

20. Signaling nucleotides

22. The stability of RNA v. DNA

24. Functions for nucleotides other than for DNA/RNA Enter ATP GTP, CTP, UTP and TTP also used in this capacity

28. NADP+ has a 2’ phosphate

30. Ribitol

32. Cobalamin Vitamin B12 Becomes Coenzyme B12

34. Fatty Acids

36. Nomenclature Saturated = -anoic acid, -anoate Unsaturated = -enoic acid, -enoate Three systems of nomenclature symbol, systematic, common Take the example of fatty acid with 16 carbons 16 carbon hydrocarbon = hexadecane Fatty acid C16:0 hexadecanoic acid (hexadecanoate) palmitic acid (palmitate) 1 double bond = C16:1, hexadecenoic acid 2 double bonds = C16:2, hexadecadienoic acid

37. Symbol Common Name Systematic Name 12:0 Lauric acid Dodecanoic acid 14:0 Myristic acid Tetradecanoic acid 16:0 Palmitic acid Hexadecanoic acid 16:1 ∆9 Palmitoleic acid 9-Hexadecenoic acid 18:0 Stearic acid Octadecanoic acid 18:1 ∆9 Oleic acid 9-octadecenoic acid 18:2 ∆9∆12 Linoleic acid 9,12-octadecadienoic acid 18:3 ∆9∆12∆15 Linolenic acid 9,12,14-octadecatrienoic acid 20:0 Arachidic acid Eicosanoic acid 20:4 ∆5∆8∆11∆14 Arachidonic acid 5,8,11,14-eicosatetraenoic acid 20:5 ∆5∆8∆11∆14∆17 Eicospentaenoic acid 5,8,11,14,17-eicosapentaenoic acid 22:0 Behenic acid Docosanoic acid 24:0 Lignoceric acid Tetracosanoic acid 24:1 ∆15 Nervonic acid 15-tetracosenoic acid

38. Storage lipids/Neutral lipids Triglycerides Triacylglycerol Sterylesters

41. Structural Lipids - Membrane components Diphytanyl lipids Sphingolipids Glycerolipids

42. Signaling Lipids Inositol containing lipids Ceramides Eicosanoids Steroids

44. Thiamine pyrophosphate (TPP)

50. Phosphohexose isomerase