Synthesis of 'head-to-tail' cyclized peptides on solid support using a chelating amide as new orthogonal protecting group

Journal of Peptide Science : an Official Publication of the European Peptide Society
Myriam Lay, Willi Bannwarth

Abstract

The synthesis of 'head-to-tail' cyclized peptides requires orthogonal protecting groups. Herein, we report on the introduction of bis(2-pyridylmethyl)amine (Bpa) as a new protecting group for carboxylic functions in SPPS. The synthesis of the Bpa-protected aspartic acid was straightforward, and its utility was investigated under standard peptide synthesis conditions. The new protecting group was cleaved in a very mild way using Cu(OAc)2 and 2-(trimethylsilyl)ethanol as nucleophile in a microwave oven without affecting other groups. Hence, the new group is ideally suited for the synthesis of 'head-to-tail' cyclic peptides, as demonstrated for a cyclic pentapeptide and cyclic hexapeptides.

References

Jan 1, 1992·Annual Review of Biochemistry·J Rizo, L M Gierasch
Jan 1, 1997·Methods in Enzymology·I AnnisG Barany
Apr 9, 1999·The Journal of Peptide Research : Official Journal of the American Peptide Society·M L ValeroD Andreu
Dec 13, 1996·The Journal of Organic Chemistry·Angelika EhrlichMichael Bienert
Sep 4, 2003·Journal of Peptide Science : an Official Publication of the European Peptide Society·John S Davies
Jan 22, 2004·Bioconjugate Chemistry·Roland HaubnerMarkus Schwaiger
May 4, 2004·Journal of Peptide Science : an Official Publication of the European Peptide Society·Maria C AlcaroAnna M Papini
Aug 4, 2004·Journal of Biotechnology·Miroslav MalesevicNorbert Sewald
Dec 22, 2004·Biotechnology Advances·Grzegorz Bulaj
Mar 3, 2010·Journal of Peptide Science : an Official Publication of the European Peptide Society·Mattan HurevichChaim Gilon
Jun 24, 2011·Nature Chemistry·Christopher J White, Andrei K Yudin

❮ Previous
Next ❯

Citations


❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Journal of Peptide Science : an Official Publication of the European Peptide Society
Raz KhandadashGerardo Byk
Journal of Peptide Science : an Official Publication of the European Peptide Society
Taku YoshiyaYuji Nishiuchi
Journal of Peptide Science : an Official Publication of the European Peptide Society
Julien TailhadesJohn D Wade
Journal of Peptide Science : an Official Publication of the European Peptide Society
Hajime HibinoYuji Nishiuchi
Environmental Science & Technology
© 2022 Meta ULC. All rights reserved