title: Preparation of acetylmercapto-3-carboxypropanoyl insulins using preparative high-performance liquid chromatography on an anion-exchange column.
abstract: A method for the preparation of insulin derivatives which have protected sulfhydryl group(s) at definite site(s) on the molecule is described. Porcine insulin reacts with S-acetylmercaptosuccinic anhydride to afford four species of insulin derivatives that have 2 (or 3)-acetylmercapto-3-carboxypropanoyl group(s) at i) Gly(A1), ii) Gly(A1) and Phe(B1), iii) Gly(A1) and Lys(B29), and iv) Gly(A1), Phe(B1) and Lys(B29) positions. The derivatives are efficiently separated in a preparative scale by anion-exchange high-performance liquid chromatography on a TSKgel DEAE-2SW column. The four derivatives are all readily deacetylated with hydroxylamine to give the corresponding sulfhydryl insulin derivatives.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
authors.forename: M
authors.initials: M
authors.lastname: Nanami
authors.forename: K
authors.initials: K
authors.lastname: Zaitsu
authors.forename: Y
authors.initials: Y
authors.lastname: Ohkura
mesh_terms: D015097:3-Mercaptopropionic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D002852:Chromatography, Ion Exchange; D007328:Insulin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013552:Swine
chemical_list: D007328:Insulin; D015097:3-Mercaptopropionic Acid