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Dolbier HW Solutions 674 - 768 AMINO ACIDS PEPTIDES AND...

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( f ) The p -nitrophenyl ester prepared in part ( e ) is an active ester. The p -nitrophenyl group is a good leaving group and can be displaced by the amino nitrogen of valine ethyl ester to form a new peptide bond. ( g ) Hydrogenolysis of the Z-protected tetrapeptide ester formed in part ( f ) removes the Z protecting group. 27.32 Consider, for example, the reaction of hydrazine with a very simple dipeptide such as Gly-Ala. Hydrazine cleaves the peptide by nucleophilic attack on the carbonyl group of glycine. It is the C-terminal residue that is cleaved as the free amino acid and identi fi ed in the hydrazinoly- sis of peptides. NHCHCO 2 H 2 NNH 2 H 3 NCH 2 C H 3 NCHCO 2 O H 2 NCH 2 CNHNH 2 O CH 3 CH 3 Gly-Ala
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