Synthesis of the partially protected fragment 1-16 of salmon calcitonin by using the phenylhydrazide protecting group.
The partially protected fragment BOC-Cys(Acm)-Ser(But)-Asn-Leu-Ser(But)-Thr(But)- Cys(Acm)-Val-Leu-Gly-Lys(epsilon-BOC)-Leu-Ser(But)-Glu(OBut)-Leu-O H of salmon calcitonin was synthesized by segment condensation in solution. Segments were synthesized in solution by the DCC/HOBt method using the phenylhydrazide as a semipermanent protecting group for protection of the carboxyl function of the C-terminal residue. The phenylhydrazide protecting group was removed by oxidation with air oxygen catalyzed by copper-pyridine complexes. The segments were then condensed by the DCC/HOBt method according to the scheme (6 + 3) + (3 + 4). The proposed synthetic scheme permits production of gram amounts of the partially protected fragment 1-16 of salmon calcitonin.
Semenov
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AN
Russian-German Joint Venture Constanta, Moscow, Russia.
Lomonosova
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IV
D000595:Amino Acid Sequence; D000818:Animals; D002116:Calcitonin / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction; D010446:Peptide Fragments / Q000138:chemical synthesis*; D010659:Phenylhydrazines / Q000737:chemistry*; D012474:Salmon
D010446:Peptide Fragments; D010659:Phenylhydrazines; C030299:phenylhydrazine; D002116:Calcitonin