Epimerization-free synthesis of cyclic peptide by use of the O-acyl isopeptide method

Journal of Peptide Science : an Official Publication of the European Peptide Society
Taku YoshiyaYoshiaki Kiso

Abstract

A head-to-tail cyclization of a protected linear hexapeptide with a C-terminal O-acyl isopeptide proceeded to give a cyclic O-acyl isopeptide without epimerization. The cyclic O-acyl isopeptide possessed different secondary structures compared with the native cyclic peptide. The isopeptide was then efficiently converted to the desired cyclic peptide via an O-to-N acyl migration reaction using a silica gel-anchored base.

References

Jul 2, 1981·Nature·D F VeberR Hirschmann
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
Jun 11, 2005·Bioorganic & Medicinal Chemistry Letters·Eric Enholm, Ashwin Bharadwaj
Jun 15, 2006·Journal of the American Chemical Society·Jens HentschelHans G Börner
Jan 20, 2007·Biopolymers·Youhei SohmaYoshiaki Kiso
Apr 19, 2007·Tetrahedron Letters·Maciej Stawikowski, Predrag Cudic
Sep 7, 2007·Journal of Peptide Science : an Official Publication of the European Peptide Society·Atsuhiko TaniguchiYoshiaki Kiso
Sep 28, 2007·Chembiochem : a European Journal of Chemical Biology·Akira ShigenagaAkira Otaka
Oct 16, 2007·Journal of Peptide Science : an Official Publication of the European Peptide Society·Irene CoinMichael Beyermann
Sep 4, 2008·Angewandte Chemie·Miquel Vila-PerellóTom W Muir
Oct 31, 2008·Organic Letters·Natalia NepomniaschiyAshraf Brik
Jan 6, 2009·Accounts of Chemical Research·Seong-Chan ParkGilbert M Nathanson
Feb 18, 2009·Chembiochem : a European Journal of Chemical Biology·Atsuhiko TaniguchiYoshiaki Kiso
May 8, 2009·Bioorganic & Medicinal Chemistry Letters·Takaaki MizuguchiKazuki Saito

❮ Previous
Next ❯

Citations

Jun 19, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Allan M PriorDianqing Sun
May 31, 2019·Chembiochem : a European Journal of Chemical Biology·Melrose Mailig, Fa Liu
Jan 21, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Vasso ApostolopoulosIstvan Toth
Apr 8, 2021·Angewandte Chemie·Hironobu HojoYoshio Hirabayashi

❮ 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.