Related Experiment Video
Updated: Oct 2, 2026

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
Published on: May 15, 2012
A practical reagent for reversible amino-protection of insulin, 3,4,5,6-tetrahydrophthalic anhydride
Y Kimura1, K Zaitsu, Y Motomura
1Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
Abstract:
Of the examined dicarboxylic acid anhydrides, 3,4,5,6-tetrahydrophthalic anhydride was found to be the best reagent in practical use for reversible amino-protection of insulin in terms of the rapidity of acid-deprotection. Twelve Gly(A1),Phe(B1),Lys(B29)-triacyl-insulins were prepared by reaction of porcine insulin with the dicarboxylic acid anhydrides and time courses for the deprotection of the acylated insulins with dilute acetic acid were investigated by means of capillary zone electrophoresis, and the tetrahydrophthalyl(THP)-insulin obtained with the reagent was the most rapidly deacylated (6 h, 25 degrees C, 0.1 M acetic acid). Isolation of triacyl-insulins and Gly(A1)-THP-, Gly(A1),Phe(B1)-diTHP- and Gly(A1),Lys(B29)-diTHP-insulins using DEAE anion-exchange high-performance liquid chromatography is also described.
More Related Videos
10:42Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
08:55Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles (PPAs) and Related Biomaterials
Published on: June 25, 2018
Related Concept Videos
Protection of Alcohols
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
Preparation of Acid Anhydrides
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Protecting Groups for Aldehydes and Ketones: Introduction
Insulin: Biosynthesis, Chemistry, and Preparation
Damage or functional impairment of β-cells inhibits insulin production, leading to diabetes. Diabetes treatment primarily uses...