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12_lec_12_2006 - SH peptides 1 and 2 can be very...

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Chemistry 5.13 Native Chemical Ligation October 6, 2008 thioester cysteine O O SR + HS peptide 1 N NH 2 H peptide 2 reversible good excellent electrophile nucleophile peptide 1 S O N H NH 2 O peptide 2 RS–H + N-to-S acyl H O shift N target protein peptide 2 N H peptide 1 O irreversible
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Unformatted text preview: SH peptides 1 and 2 can be very large (utility) very mild reaction conditions (compatibility/tolerance) side reactions common to polypeptide synthesis avoided (higher yield) requires that target protein contain ( Cys ); best if near the middle of the sequence...
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