title: Synthesis and properties of [A19-(p-fluorophenylalanine)] insulin.
abstract: The synthesis of [Phe(F)A19]insulin (porcine) is described. First the protected [Phe(F)19]A-chain was assembled by segment condensation of [1-12] and [13-21] using the dicyclohexyldiimide/1-hydroxybenzotriazole procedure. [Phe(F)19]A-chain was purified by ion exchange chromatography after removal of all the protecting groups (Boc, But, OBut and S-Trt) and its conversion into the tetra-S-sulfonated derivative. [Phe(F)A19]insulin was prepared by combination with porcine B-chain and purified by gel filtration and ion-exchange chromatography. The in vitro biological activity of this analogue was 60%. CD spectra in the near and far UV are qualitatively very similar to those of insulin.
authors.affiliation: Institute of Molecular Biology, Bulgarian Academy of Sciences, Sofia.
authors.forename: S
authors.initials: S
authors.lastname: Stoev
authors.forename: S
authors.initials: S
authors.lastname: Zakhariev
authors.forename: E
authors.initials: E
authors.lastname: Golovinsky
authors.forename: H G
authors.initials: HG
authors.lastname: Gattner
authors.forename: V K
authors.initials: VK
authors.lastname: Naithani
authors.forename: A
authors.initials: A
authors.lastname: Wollmer
authors.forename: D
authors.initials: D
authors.lastname: Brandenburg
mesh_terms: D000273:Adipose Tissue / Q000187:drug effects / Q000378:metabolism; D000596:Amino Acids / Q000032:analysis; D000818:Animals; D002942:Circular Dichroism; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D007328:Insulin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D009904:Optical Rotation; D011487:Protein Conformation; D051381:Rats
chemical_list: D000596:Amino Acids; D007202:Indicators and Reagents; D007328:Insulin; C059266:insulin, 4-fluorophenylalanine(A19)-