title: Preparation and application of Nalpha-B1,Nepsilon-B29-bis (ter.-butyloxycarbonyl)insulin.
abstract: Two methods are described for the preparation of NalphaB1,Nepsilon29-Boc2-insulin from Nalpha A1-trifluoroacetyl-insulin and Nalpha A1-citraconyl-insulin in 80 - 90% and 65% yields, respectively. Removal of the Boc protections afforded the fully active insulin. Application of this derivative was demonstrated by the preparations of des-GlyA1-insulin and [A1-guanidinoacetyl]insulin. The former compount exhibited 2% activity in the in vitro free fat cell assay and the latter 88 +/- 5% while NalphaB1-NepsilonB29-Boc2-insulin showed 45 +/- 3% activity only.
mesh_terms: D000596:Amino Acids; D000818:Animals; D001386:Azides / Q000494:pharmacology; D002417:Cattle; D002852:Chromatography, Ion Exchange; D003619:Dansyl Compounds; D004588:Electrophoresis, Cellulose Acetate; D004590:Electrophoresis, Paper; D007328:Insulin / Q000031:analogs & derivatives* / Q000302:isolation & purification; D014269:Trifluoroacetic Acid / Q000378:metabolism
chemical_list: D000596:Amino Acids; D001386:Azides; D003619:Dansyl Compounds; D007328:Insulin; D014269:Trifluoroacetic Acid