An improved synthesis of crystalline mammalian glucagon
- 1 December 1984
- journal article
- research article
- Published by Wiley in European Journal of Biochemistry
- Vol. 145 (3), 601-605
- https://doi.org/10.1111/j.1432-1033.1984.tb08599.x
Abstract
Mammalian glucagon was synthesized by the stepwise solid-phase method using several improvements developed in recent years. Peptide was assembled on a 4-(oxymethyl)phenylacetamidomethyl-copoly(styrene-divinyl benzene) resin support with N.alpha.-t-butoxycarbonyl and benzyl-based side-chain protection for most of the trifunctional amino acids. Crude synthetic glucagon was obtained in 75% yield by deprotection and cleavage from the resin with a new modified HF procedure. Pure material was isolated in 48% overall yield by a 1-step purification on preparative C18 reverse-phase chromatography. It was crystallized from aqueous solution at pH 9.2. The synthetic glucagon activated adenylate cyclase in rat liver membranes in the same manner as natural glucagon, with both achieving half-maximal activation at a concentration of 7 nM.This publication has 20 references indexed in Scilit:
- [25-Oxindolylalanine]glucagon and [27-methionine sulfoxide]glucagon: preparation, purification, and characterizationBiochemistry, 1982
- Weak acid‐catalyzed pyrrolidone carboxylic acid formation from glutamine during solid phase peptide synthesisInternational Journal of Peptide and Protein Research, 1982
- Improved deprotection in solid phase peptide synthesis: deprotection of Ni-formyl-tryptophan to tryptophan in low concentrations of HF in Me2S–p- thiocresol mixturesJournal of the Chemical Society, Chemical Communications, 1982
- Solid-phase synthesis of crystalline glucagonBiochemistry, 1981
- A quantitative evaluation of methods for coupling asparagineThe Journal of Organic Chemistry, 1980
- Nα-Trinitrophenyl glucagon An inhibitor of glucagon-stimulated cyclic AMP production and its effects on glycogenolysisBiochimica et Biophysica Acta (BBA) - General Subjects, 1979
- A new synthetic route to tert-butyloxycarbonylaminoacyl-4-(oxymethyl)phenylacetamidomethyl-resin, an improved support for solid-phase peptide synthesisThe Journal of Organic Chemistry, 1978
- Synthesis of a nonadecapeptide corresponding to residues 37-55 of ovine prolactin. Detection and isolation of the sulfonium form of methionine-containing peptidesJournal of the American Chemical Society, 1976
- The monitoring of reactions in solid-phase peptide synthesis with picric acidAnalytica Chimica Acta, 1972
- Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid unter Zusatz von 1‐Hydroxy‐benzotriazolenEuropean Journal of Inorganic Chemistry, 1970