Pseudo-Wang Handle for the Preparation of Fully Protected Peptides. Synthesis of Liraglutide by Fragment Condensation

Daniel Carbajo; Peter Fransen; Ayman El-Faham; Miriam Royo; Fernando Albericio

doi:10.1021/acs.orglett.9b00813

Pseudo-Wang Handle for the Preparation of Fully Protected Peptides. Synthesis of Liraglutide by Fragment Condensation

Org Lett. 2019 Apr 5;21(7):2459-2463. doi: 10.1021/acs.orglett.9b00813. Epub 2019 Mar 14.

Authors

Daniel Carbajo^{1

2}, Peter Fransen¹, Ayman El-Faham^{3

4}, Miriam Royo^{1

2}, Fernando Albericio^{1

2

3

5

6}

Affiliations

¹ CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine , University of Barcelona , 08028 Barcelona , Spain.
² Institute of Advanced Chemistry of Catalonia (IQAC-CSIC) , Spanish National Research Council (CSIC) , 08034 Barcelona , Spain.
³ Department of Chemistry, College of Science , King Saud University , 2455, Riyadh 11451 , Saudi Arabia.
⁴ Department of Chemistry, Faculty of Science , Alexandria University , 426, Alexandria 21321 , Egypt.
⁵ Department of Organic Chemistry , University of Barcelona , 08028 Barcelona , Spain.
⁶ School of Chemistry and Physics , University of KwaZulu-Natal , Durban 4001 , South Africa.

PMID: 30869905
DOI: 10.1021/acs.orglett.9b00813

Abstract

A handle for the protection of the C-terminus of peptides after cleaving with low concentration of trifluoroacetic acid (2-4%) is reported. The handle prevents polymerization reactions in the convergent condensation of peptidic fragments. Moreover, it is traceless, being removed during the final deprotection step of the peptide synthesis. This cheap and convenient handle is easily attached to the solid support, causing no disturbance to peptide elongation and thus proving to be useful in the convergent synthesis of long peptides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acid Sequence
Liraglutide
Peptide Fragments / chemical synthesis*
Peptide Fragments / chemistry
Peptides / chemical synthesis*
Peptides / chemistry
Trifluoroacetic Acid / chemistry*

Substances

Peptide Fragments
Peptides
Liraglutide
Trifluoroacetic Acid