Synthesis of a partially purified fragment of salmon calcitonin 1-16 using a phenylhydrazide protective group
Semenov, A.N.; Lomonosova, I.V.
Bioorganicheskaia Khimiia 19(2): 182-189
1993
ISSN/ISBN: 0132-3423 PMID: 8498959 Document Number: 414262
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.