aaPeptide - Chem234OrganicChemistryII...

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Chem 234 Organic Chemistry II   Professor Duncan J. Wardrop University of Illinois at Chicago Spring 2004 H N N Cl O N 3 HO N NH O O CH 3 N H H N Br O O Br N O O N H H H H H O MeO O O OMe OMe O OMe O HO O O O O HO N CO 2 H S O HN NH H H H HO N N CF 3 CH 3 H 2 NSO 2 Cl Cl Cl OH
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Chapters Covered: 1. Today:  Chapter 27  (amino acids, etc), Part 1 2. Thursday:  Chapter 27  (amino acids, etc), Part 2 3. Tuesday, April 20 :  Chapter 25  (carbohydrates),  Part 1 4. Thursday, April 22:  Chapter 25  (carbohydrates),  Part 2 5. Tuesday, April 27:  Chapter 28  (nucleic acids) 6. Thursday, April 29 (last meeting):  Review Session    Chem 234 - Now to Finals Week
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Chapter 27  Amino Acids, Peptides, and Proteins
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Topics Covered: 1. Amino Acids 1. Stereochemistry of  α- Amino Acids 1. Common  α- Amino Acids: Review of Structure 1. Effect of pH on the Structure of  α- Amino Acids 1. Isoelectric Point of Amino Acids    1. Preparation of  α- Amino Acids: Alkylation, Strecker  Synthesis 1. Reactions of  α- Amino Acids:  N- Acylation, Esterification,  Ninhydrin Today’s Lecture
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27.1  Classification of Amino Acids
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Classification of Amino Acids amino  acids  are  classified  as  α, β, γ etc .  to indicate where the nitrogen atom is relative to the carboxylic acid: O O N H H H α-Αμ ινο Αχιδ α Ο Ο Ν Η β-Αμ ινο Αχιδ Η Ν α β Ο Ο Η γ-Αμ ινο Αχιδ Ν α β Η Η γ
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Selected Amino Acids 1-Aminocyclopropanecarboxylic Acid an  α -amino acid that is an intermediate in the biosynthesis of ethylene 3-Aminopropanoic Acid β -amino acid that is one  of the structural units present  in coenzyme A 4-Aminobutanoic Acid   γ -amino acid involved in the transmission of nerve impulses α O O N H H N a b O O H N a b H H g NH 2 O OH
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α- Amino Acids are Most  Ubiquitous in Nature O O N H H H α-Αμ ινο Αχιδ α Ο Ο Ν Η β-Αμ ινο Αχιδ Η Ν α β Ο Ο Η β-Αμ ινο Αχιδ Ν α β Η Η γ
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Revision: Amines are Brønsted Bases N H X N X Amines are electron-rich and have a reactive lone pair, which can form a covalent bond to a proton to form an ammonium ion.
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Amino Acids Exist as Zwitterions While  their  name  implies  that  amino  acids are  compounds  that  contain  an  amine  (— NH 2 )  and  a  carboxylic  acid  (-CO 2 H),  these groups  are  actually  present  as  their conjugate  acid  (—NH 3 + )  and  conjugate base (—CO 2 ), respectively .
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Amino Acids Exist as Zwitterions Basic Amine Acidic Carboxylic Acid O O N H H H α O O N H H α Η O O N H H α Η Resonance-Stabilized Zwitterion
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Zwitterions Defined Zwitterionic Compounds/Zwitterions neutral  compounds  having  formal  unit  electrical charges  of  opposite  sign.  Some  chemists  restrict
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This note was uploaded on 09/30/2011 for the course CHEM ORGANIC CH taught by Professor Dotsevisogah during the Spring '09 term at Cornell University (Engineering School).

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aaPeptide - Chem234OrganicChemistryII...

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