Dolbier HW Solutions 668

Dolbier HW Solutions 668 - 2 COCH 2 O O O O CH 2 C 6 H 5...

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The amino group of glycine is then exposed by removal of the protecting group. Typical conditions for this step involve treatment with hydrogen chloride in acetic acid. To attach phenylalanine to resin-bound glycine, we must f rst protect the amino group of phenyl- alanine. A Boc protecting group is appropriate. Peptide bond formation occurs when the resin-bound glycine and Boc-protected phenylalanine are combined in the presence of DCCI. Remove the Boc group with HCl and then treat with HBr in tri F uoroacetic acid to cleave Phe-Gly from the solid support. 27.21 The numbering of the ring in uracil and its derivatives parallels that in pyrimidine. Pyrimidine 1 2 3 4 5 6 N N Uracil 1 2 3 4 5 6 N H O HN O 5-Fluorouracil 5 N H F O HN O Boc-Protected, resin-bound Phe-Gly (CH 3 ) 3 COCNHCHCNHCH
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Unformatted text preview: 2 COCH 2 O O O O CH 2 C 6 H 5 resin 1. HCl, acetic acid 2. HBr, trifluoroacetic acid H 3 NCHCNHCH 2 CO 2 2 1 CH 2 C 6 H 5 Phe-Gly (CH 3 ) 3 COCNHCHCO 2 H 1 O Boc-Protected phenylalanine Boc-Protected, resin-bound Phe-Gly CH 2 C 6 H 5 (CH 3 ) 3 COCNHCHCNHCH 2 COCH 2 O O O CH 2 C 6 H 5 H 2 NCH 2 COCH 2 resin O resin DCCI Resin-bound glycine (CH 3 ) 3 COCCl (CH 3 ) 3 COCNHCHCO 2 H H 3 NCHCO 2 2 O 1 O 1 tert-Butoxycarbonyl chloride Phenylalanine Boc-Protected phenylalanine CH 2 C 6 H 5 CH 2 C 6 H 5 (CH 3 ) 3 COCNHCH 2 COCH 2 resin O O H 2 NCH 2 COCH 2 resin O HCl acetic acid Boc-Protected, resin-bound glycine Resin-bound glycine 762 AMINO ACIDS, PEPTIDES, AND PROTEINS. NUCLEIC ACIDS...
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