Dolbier HW Solutions 673

Dolbier HW Solutions 673 - 2 H CH 2 O O O C O NH 2 CH 2 OH...

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( c ) Phenyl isothiocyanate is a reagent used to identify the N-terminal amino acid of a peptide by the Edman degradation. The N-terminal amino acid is cleaved as a phenylthiohydantoin (PTH) derivative, the remainder of the peptide remaining intact. ( d ) Benzyloxycarbonyl chloride reacts with amino groups to convert them to amides. The only free amino group in Asn-Ser-Ala is the N terminus. The amide function of asparagine does not react with benzyloxycarbonyl chloride. ( e ) The Z-protected tripeptide formed in part ( d ) is converted to its C-terminal p -nitrophenyl ester on reaction with p -nitrophenol and N , N -dicyclohexylcarbodiimide (DCCI). 1 p -Nitrophenol OH O 2 N Z-Asn-Ser-Ala C 6 H 5 CH 2 OCNHCHCNHCHCNHCHCO
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Unformatted text preview: 2 H CH 2 O O O C O NH 2 CH 2 OH CH 3 DCCI Z-Asn-Ser-Ala p-nitrophenyl ester NO 2 C 6 H 5 CH 2 OCNHCHCNHCHCNHCHCO CH 2 O O O C O NH 2 CH 2 OH CH 3 O 1 Benzyloxycarbonyl chloride C 6 H 5 CH 2 OCCl O Asn-Ser-Ala CH 2 CH 2 OH CH 3 H 3 NCHCNHCHCNHCHCO 2 2 1 O O Z-Asn-Ser-Ala C 6 H 5 CH 2 OCNHCHCNHCHCNHCHCO 2 H O O O CH 2 CH 2 OH CH 3 C O NH 2 C O NH 2 Ile-Glu-Phe CH 3 CH 2 CH CH 2 CH 2 CO 2 H CH 3 CH 2 C 6 H 5 H 3 NCHCNHCHCNHCHCO 2 2 1 O O 1. C 6 H 5 N 2. HBr, nitromethane C S 1 Glu-Phe H 3 NCHCNHCHCO 2 2 1 CH 2 CH 2 CO 2 H CH 2 C 6 H 5 O PTH derivative of isoleucine CHCH 2 CH 3 CH 3 S O N C 6 H 5 HN AMINO ACIDS, PEPTIDES, AND PROTEINS. NUCLEIC ACIDS 767...
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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