2006springlastlecture-aminoacids

2006springlastlecture-aminoacids - Organic Chemistry 140C...

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Organic Chemistry 140C June 8, 2006 Last lecture…
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R H 3 N O O Amino acids, Peptides and Proteins α -Amino acids
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Amino acids - Synthesis OH O Br 2 , PBr 3 OH O Br NH 3 O O H 3 N rac - Alanine N 3 ! OH O N 3 H 2 (cat.) O O H 3 N H O NH 3 H HN H C N C N H 2 N H H 3 O + , H 2 O ! OH C O H 3 N Strecker Synthesis:
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OEt O EtO O OEt O EtO O R H 3 O + , H 2 O, ! " CO 2 OH O R EtO " , R X OEt O EtO O Br N O O OEt O EtO O N O O H EtO ! , R X OEt O EtO O N O O R H 3 O + , H 2 O, ! " CO 2 OEt O EtO O N O O R OH O HO O NH 3 R OH O NH 3 R A more general solution - Gabriel Synthesis:
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R H 3 N O H O R H 3 N O O R H 2 N O O p K a1 ~ 2.5 pH 0 13 p K a2 ~ 9.5 Acid/Base Properties pI = p K 1 + p K 2 2 Charge: 1+ 0 1 - @ pH = pI [zwitterionic structure] is greatest!
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pH O H O O O % 50 0 100 p K a At pH = p K a , 50% ionization
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Primary Structure of Peptides/Proteins = Amino Acid Sequence H 2 N O R 2 N N O R 4 N H N O R 1 O H H H R 3 R 5 O R n-1 N N O OH O H H R n O N R 1 H O N R 1 H Double bond character
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2 N O R 2 N N O R 4 N H N O R 1 O H H H R 3 R 5 O R n-1 N N O OH O H H R n R 2 H 2 N O OH R 4 H 2 N O OH R n-1 H 2 N O OH H 2 N O R 1 OH H 2 N O R 3 OH H 2 N O R 5 OH H 2 N O OH R n 6N HCl, 110 o C, 24h 1. Determine amino acid composition Result : 3 Ala, 1 Asp, 5 Leu…. . Mechanism: acid catalyzed
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This note was uploaded on 09/18/2010 for the course CHEM 140C taught by Professor Nefzi during the Spring '06 term at UCSD.

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2006springlastlecture-aminoacids - Organic Chemistry 140C...

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