[Synthesis of a partially purified fragment of salmon calcitonin 1-16 using a phenylhydrazide protective group].
The partially protected fragment Boc-Cys(Acm)-Ser(Bu(t))-Asn-Leu-Ser(Bu(t))-Thr (Bu(t))-Cys(Acm)-Val-Leu-Gly-Lys(Boc)-Leu-Ser(Bu(t))-Gln-Glu(OBu(t ))- Leu-OH of salmon calcitonin was synthesized by the segment condensation in solution. Segments were synthesized by the DCC/HOBt method in solution with phenylhydrazide as a semipermanent protecting group for the carboxyl function of the C-terminal residue. The phenylhydrazide group was removed by oxidation with air oxygen catalyzed by copper pyridine complexes under mild conditions. The segments were then condensed by the DCC/HOBt method according to the scheme (6 + 3) + (3 + 4). The proposed scheme makes it possible to product the partially protected fragment 1-16 of salmon calcitonin on the gram scale.
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Semenov
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Lomonosova
D000595:Amino Acid Sequence; D000818:Animals; D002116:Calcitonin / Q000138:chemical synthesis*; D002384:Catalysis; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry; D010446:Peptide Fragments / Q000138:chemical synthesis*; D010659:Phenylhydrazines / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry
D010446:Peptide Fragments; D010659:Phenylhydrazines; D011725:Pyridines; C030299:phenylhydrazine; C028815:salmon calcitonin; D002116:Calcitonin; C023666:pyridine; D010100:Oxygen
Sintez chastichno zashchishchennogo fragmenta 1-16 kal'tsitonina lososia s ispol'zovaniem fenilgidrazidnoĭ zashchitnoĭ gruppy.