A convergent liquid-phase synthesis of salmon calcitonin.
Salmon calcitonin (sCT) was prepared in good yield and high purity by the condensation of Nalpha-Boc-cyclic decapeptide, Boc-C1SNLSTC7VLG-OH (1,7-disulfide), with protected docosapeptide (Psc)LSQE(OPse)LHK(Psc)LQTYPRTNTGSGTP-NH2 x 3TFA, followed by deprotection of Boc with trifluoroacetic acid and Psc/Pse with piperidine. The 2-(phenylsulfonyl)ethoxycarbonyl (Psc) and 2-(phenylsulfonyl)ethyl (Pse) protecting groups were recently developed. The two peptides were built up by stepwise and fragment condensation using appropriate Nalpha-Boc-amino acids and subsequent deprotection in solution. The synthetic sCT exhibited hypocalcemic potency of more than 4000 IU/mg in rats.
Lee
Y S
YS
Research Institute, Hyundai Pharm. Inc. Co., Ltd., Bucheon, Korea. ynsnlee@hyundaipharm.co.kr
Lee
H J
HJ
Pozdnyakov
P I
PI
Samukov
V V
VV
Kim
H J
HJ
D000595:Amino Acid Sequence; D000818:Animals; D002116:Calcitonin / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005563:Formic Acid Esters / Q000737:chemistry; D006996:Hypocalcemia / Q000139:chemically induced; D008969:Molecular Sequence Data; D051381:Rats
D005563:Formic Acid Esters; C000345:t-butyloxycarbonyl group; C028815:salmon calcitonin; D002116:Calcitonin