Synthesis of 1,4-Oxazepane-2,5-diones via Cyclization of Rotationally Restricted Amino Acid Precursors and Structural Reassignment of Serratin

The Journal of Organic Chemistry
Ewout RuysberghSven Mangelinckx

Abstract

Several natural products containing a 1,4-oxazepane-2,5-dione-core are known. One example is serratin, isolated from Serratia marcescens. Because of the presence of a carboxylic amide, which has a preference for a trans-conformation, and the presence of a labile lactone in this core, many synthetic methodologies commonly used for the cyclization toward medium-sized heterocycles cannot be applied. As N-acyl amino acids lacking a third substituent at nitrogen failed to undergo ring-closure, several N-protecting groups were evaluated. With the use of the removable PMB-group, an N-unsubstituted 1,4-oxazepane-2,5-dione was synthesized. Via the application of pseudoprolines (i.e. serine-derived oxazolidines as another type of protecting group), a compound with the presumed structure of the natural product serratin was obtained. As a result of the differences in spectral data, the incorrect structural assignment of the natural product serratin was identified. Instead of the predicted seven-membered heterocycle, a symmetrical serratamolide analogue is proposed to be the correct structure of serratin.

References

Aug 1, 1987·Journal of Medicinal Chemistry·M OgataY Kawamura
Jul 1, 1986·Journal of Medicinal Chemistry·C G PittJ Metterville
Mar 1, 1972·Journal of Bacteriology·A Eberhard
Oct 21, 1970·Journal of the American Chemical Society·C M DeberE R Blout
Sep 16, 1994·Journal of Medicinal Chemistry·F E KoehnJ K Reed
Jan 3, 1997·The Journal of Biological Chemistry·L R DickR L Stein
Oct 18, 2001·Journal of the American Chemical Society·J R PorterM L Snapper
Dec 12, 2002·Biochemistry·William J WedemeyerHarold A Scheraga
Jul 10, 2003·Chemical Reviews·Christophe Dugave, Luc Demange
Aug 30, 2003·Organic & Biomolecular Chemistry·Hans BieräugelJan H van Maarseveen
Dec 1, 1957·The Biochemical Journal·N J CARTWRIGHT
Sep 23, 2003·Angewandte Chemie·Olivier DavidJan H van Maarseveen
Jul 22, 2004·Bioorganic & Medicinal Chemistry·Francesca AielloNouri Neamati
Dec 4, 2004·The Journal of Organic Chemistry·Danielle SkropetaPeter Turner
Dec 30, 2004·Proceedings of the National Academy of Sciences of the United States of America·Gunnar F KaufmannKim D Janda
Jul 15, 2005·Proceedings of the National Academy of Sciences of the United States of America·Andrew P BroganKim D Janda
Jun 20, 2006·Bioorganic & Medicinal Chemistry Letters·Peter JeschkeHans-Christoph Weiss
Jul 31, 2007·Journal of the American Chemical Society·James J FlemingJ Du Bois
Sep 28, 2007·Journal of Oleo Science·Eiko OshimuraKazutami Sakamoto
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Feb 29, 2008·Journal of Natural Products·Deepti DwivediVictor Wray
Jul 7, 2012·Chemical Communications : Chem Comm·Jochem P A RuttersJan H van Maarseveen
Sep 15, 2012·Organic & Biomolecular Chemistry·Khanh HaAlan R Katritzky
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Jun 14, 2016·Integrative Biology : Quantitative Biosciences From Nano to Macro·Frances Y McWhorterWendy F Liu

❮ Previous
Next ❯

Citations

Dec 15, 2020·Organic & Biomolecular Chemistry·Ardalan A NabiJonathan Sperry
Oct 1, 2021·Chemical Communications : Chem Comm·Álvaro Velasco-RubioCarlos Saá

❮ 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.