title: [Synthesis of a [Glu5, Ala12, Ala18, Ala21]sheep insulin-A-chain by fragment condensation on a polymer support (author's transl)].
abstract: The synthesis of a [Glu5, Ala12, Ala18,-Ala21]sheep insulin-A-chain by condensation of 5 fragments on a polymer support is described. The 5 fragments Boc-Gly-Ile-Val-Glu(gammaOBut)-Glu(gammaOBut) (V), Boc-Cys(SiPr) (IV), Boc--Cys(SiPr)-Ala-Gly-Val (III), Boc-Cys(SiPr)-Ala-Leu-Tyr-Gln-Leu (II) and Boc-Glu(gammaOBut)-Ala--Tyr(Bzl)-Cys(SiPr)-N2H3 (I) were synthesized by conventional methods and coupled with dicyclohexylcarbodiimide/1-hydroxybenzotriazol (II, III, IV, V) and by the azide method (I) with coupling yields of 60-98% on an Ala-polymer. The failure sequence peptides were separated by ion exchange chromatography on DEAE-Sephadex and by chromatography on Biogel P4. The A-chain was obtained in 9% yield, which, after combinations with natural B-chain, gave insulin activities comparable to that obtained with natural A-chain. These results demonstrate that fragment condensation by the solid-phase method together with simple techniques for purification can be used for the synthesis of longer peptides.
mesh_terms: D000818:Animals; D002852:Chromatography, Ion Exchange; D007328:Insulin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification; D008722:Methods; D009842:Oligopeptides / Q000138:chemical synthesis; D009904:Optical Rotation; D012756:Sheep
chemical_list: D007328:Insulin; D009842:Oligopeptides
vernacular_title: Synthese einer [Glu5, Ala12, Ala18, Ala21]Schafinsulin-A-Kette durch Fragmentkondensation am Festkörper