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Transcript
Armstrong Foothill College CHEM 12C OUTLINE: KLEIN CHAPTER 25: AMINO ACIDS AND POLYPEPTIDES 1) Amino Acid Structure A) Stereochemistry B) Acid/Base properties C) Zwitterion D) pI definition and calculations E) Gel electrophoresis 2) Synthesis of Amino Acids A) Hell-Volhard-Zelinsky: Carboxylic acid to α-haloacid then SN2 reaction w excess ammonia B) Streker Synthesis: Aldehyde with NH4Cl and NaCN C) Amido Malonate Synthesis: Diethyl acetamidomalonate alkylation, hydrolysis and decarboxylation 3) Peptides : Primary structure A) The peptide bond B) Hindered rotation and 1H NMR C) Sequencing via Selective Cleavage i) With aqueous acid at every peptide bond ii) Edman Degradation: N terminus iii) DNFB to identify N-terminus iv) Chymotripsin at C-terminus v) With cyanogen bromide BrCN at methionine C terminus vi) With chymotripsin at C end of phe, tyr, trp vii) With Tripsin at C end of lys, arg D) Separation and Identification of aa fragments via Gel electrophoresis, Ionexchange chromatography, and Mass Spectrometry 4) Peptide Synthesis A) Traditional solution synthesis i) Role of DCC ii) N-protecting groups: BOC and FMOC iii) C-protecting groups: PhCH2OH and 1° ROH B) Merrifield Solid Phase synthesis LEARNING OUTCOMES: 1) Deduce a polypeptide structure from a series of selective enzyme cleavage experimental results. 2) Propose the synthesis of a racemic amino acid from an aldehyde or carboxylic acid. 3) Interpret the 1H NMR of a dipeptide 4) Predict the structure/ proton state of an amino acid at any given pH. EXAMPLE PROBLEMS: 1) 2) Name and draw the amino acid formed in the following reaction sequence O O H3O+ 1. NaOEt EtO OEt 2. 1-chloro-2-methylpropane heat HN O 3) Use three letter codes to identify the following polypeptide: SH O O H N H N H2N N H O OH O OH