Studies on Peptides. CLVI. Synthesis of Second Human Calcitonin Gene-Related Peptide (β-hCGRP) by Application of a New Disulfide-Bonding Reaction with Thallium (III) Trifluoroacetate

NOBUTAKA FUJII; TOSHIHIRO WATANABE; AKIRA OTAKA; KIYOSHI BESSHO; ITSUO YAMAMOTO; TOSHIHARU NODA; HARUAKI YAJIMA

doi:10.1248/cpb.35.4769

NOBUTAKA FUJII, TOSHIHIRO WATANABE, AKIRA OTAKA, KIYOSHI BESSHO, ITSUO YAMAMOTO, TOSHIHARU NODA, HARUAKI YAJIMA

著者情報

キーワード: second human calcitonin gene-related peptide synthesis, new disulfide bonding reaction, thallium trifluoroacetate oxidation, air-oxidized disulfide bonding reaction, Met (O) reduction, ammonium iodide, trimethylsilyl trifluoromethanesulfonate deprotection, hard-acid deprotection, soft base, diphenyl sulfide, inhibitory bone calcium resorption, lowering serum calcium, lowering serum phosphate ion

ジャーナルフリー

1987 年 35 巻 12 号 p. 4769-4776

DOI https://doi.org/10.1248/cpb.35.4769

詳細

抄録

A 37-residue peptide corresponding to the entire amino acid sequence of second human calcitonin gene-related peptide (β-hCGRP) was synthesized by assembling seven peptide fragments, followed by two successive treatments; i.e., first with thallium (III) trifluoroacetate to establish the disulfide bond between two Cys (Ad) residues and then with 1 M trimethylsilyl trifluoromethane-sulfonate/trifluoroacetic acid in the presence of diphenyl sulfide and ammonium iodide to remove all protecting groups employed and at the same time to reduce Met (O) to Met. The result was compared with that obtained by the usual air-oxidation procedure.
Synthetic β-hCGRP exhibited a weak inhibitory action against bone Ca-resorption stimulated by [1-34] -parathyroid hormone in vitro and lowered the Ca and Pi levels in rat serum.

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