Chiroptical properties of streptorubin B: the synergy between theory and experiment

Chirality
Marta S AndradeHenry S Rzepa

Abstract

Analysis of the calculated and measured optical rotation (OR) together with other calculated chiroptical properties such as electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) of the prodigiosin alkaloid streptorubin B shows that these are dominated by the pseudoenantiomeric atropisomers anti-(S)-streptorubin B (1A) and syn-(S)-streptorubin (1B). Atropisomerism is a dynamic phenomenon with a potentially nonequilibrium population of isomers, and accordingly the measured chiroptical responses may vary with time, concentration, temperature, and the anion of the salts used. Streptorubin also has the potential to form stacked homodimers for which the optical rotations measured at 589 nm can vary greatly due to the presence of ECD-active electronic transitions in this region.

References

Feb 26, 1969·Journal of the American Chemical Society·H H WassermanD D Keith
Aug 30, 2001·Journal of the American Chemical Society·P E Harrington, M A Tius
Aug 30, 2001·Journal of the American Chemical Society·D L Boger, J Hong
Nov 17, 2006·Nature Reviews. Microbiology·Neil R WilliamsonGeorge P C Salmond
Mar 31, 2007·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Prasad L Polavarapu
Nov 29, 2007·Future Microbiology·Neil R WilliamsonGeorge P C Salmond
Jun 17, 2008·Journal of Natural Products·Takashi KawasakiYoichi Hayakawa
Apr 22, 2009·Accounts of Chemical Research·Parag MukhopadhyayDavid N Beratan
Dec 21, 2010·Journal of the American Chemical Society·Stuart W HaynesGregory L Challis
Dec 21, 2010·Journal of the American Chemical Society·Dennis X HuRegan J Thomson
Jul 21, 2012·The Journal of Organic Chemistry·María García-ValverdeRoberto Quesada
Mar 5, 2013·Journal of the American Chemical Society·James H Frederich, Patrick G Harran

❮ Previous
Next ❯

Citations

May 11, 2018·Chirality·Daniela PeixotoPrasad L Polavarapu

❮ 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.