Evaluation of stereochemically dense morpholine-based scaffolds as proline surrogates in beta-turn peptides

Organic & Biomolecular Chemistry
Filippo SladojevichAndrea Trabocchi

Abstract

Four peptides differing for the structure of the new morpholine-based heterocyclic compound acting as a turn inducer were synthesized in solution phase, and the conformational preferences were assessed by means of NMR analysis. All spectroscopic data revealed an adaptive behaviour of the turn peptides in generating turn conformations stabilized by intramolecular hydrogen-bonds, despite the conformational changes of the turn inducer. Thus, this study suggests the possibility of functionalizing morpholine-containing beta-turn peptides with no significant loss of the secondary framework. The 3,4-dihydro-2H-[1,4]oxazine-containing peptide showed a more compact structure stabilized by an additional gamma-turn-forming hydrogen-bond experienced by the Gly amide proton.

References

Jan 1, 1992·Annual Review of Biochemistry·J Rizo, L M Gierasch
Jan 1, 1985·Advances in Protein Chemistry·G D RoseJ A Smith
May 24, 2000·Organic Letters·Y FengK Burgess
Sep 18, 2001·The Journal of Organic Chemistry·E AlonsoJ González
Oct 25, 2001·The Journal of Organic Chemistry·Michael J. Soth, James S. Nowick
Oct 26, 2002·The Journal of Organic Chemistry·M Montserrat FernándezErnest Giralt
Dec 8, 2004·Bioorganic & Medicinal Chemistry Letters·Jun ChibaAngela Wong
Aug 9, 2005·Bioorganic & Medicinal Chemistry Letters·J I LevinJ S Skotnicki
Feb 1, 2006·Organic & Biomolecular Chemistry·David BlombergJan Kihlberg
May 1, 2007·The Journal of Organic Chemistry·Filippo SladojevichAntonio Guarna
Jun 27, 2007·Journal of the American Chemical Society·Gorka PerisScott J Miller
Dec 13, 2007·Chemical Reviews·Elizabeth A Colby DavieScott J Miller
Sep 20, 2008·Organic & Biomolecular Chemistry·Filippo SladojevichAntonio Guarna

❮ Previous
Next ❯

Citations

Aug 24, 2012·Chemical Communications : Chem Comm·Kuruppanthara N VijayadasGangadhar J Sanjayan
Aug 26, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Monika KovačevićLidija Barišić
May 7, 2015·Biochemistry·Jiun Ru WongFangwei Shao
Aug 27, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Monika KovačevićLidija Barišić
May 8, 2019·Chembiochem : a European Journal of Chemical Biology·Charlène GadaisSteven Ballet

❮ 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.