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


Journal

Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393

Informations de publication

Date de publication:
05 04 2019
Historique:
pubmed: 15 3 2019
medline: 20 8 2019
entrez: 15 3 2019
Statut: ppublish

Résumé

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.

Identifiants

pubmed: 30869905
doi: 10.1021/acs.orglett.9b00813
doi:

Substances chimiques

Peptide Fragments 0
Peptides 0
Liraglutide 839I73S42A
Trifluoroacetic Acid E5R8Z4G708

Types de publication

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

Langues

eng

Pagination

2459-2463

Auteurs

Daniel Carbajo (D)

CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine , University of Barcelona , 08028 Barcelona , Spain.
Institute of Advanced Chemistry of Catalonia (IQAC-CSIC) , Spanish National Research Council (CSIC) , 08034 Barcelona , Spain.

Peter Fransen (P)

CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine , University of Barcelona , 08028 Barcelona , Spain.

Ayman El-Faham (A)

Department of Chemistry, College of Science , King Saud University , 2455, Riyadh 11451 , Saudi Arabia.
Department of Chemistry, Faculty of Science , Alexandria University , 426, Alexandria 21321 , Egypt.

Miriam Royo (M)

CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine , University of Barcelona , 08028 Barcelona , Spain.
Institute of Advanced Chemistry of Catalonia (IQAC-CSIC) , Spanish National Research Council (CSIC) , 08034 Barcelona , Spain.

Fernando Albericio (F)

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

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Classifications MeSH