Absolute configurational determination of an all-trans-retinal dimer isolated from photoreceptor outer segments

Chirality
Nathan FishkinNina Berova

Abstract

An all-trans-retinal (ATR) dimer (1) isolated from photoreceptor outer segments was found to have a stereogenic center at C13' flanked by tetraene (295 nm) and hexaenal (438 nm) chromophores. Analytical chiral HPLC (Chiralcel OD) revealed that the isolated retinoid had formed in 13% enantiomeric excess. Using a combination of (1)H-(1)H NOESY constraints, molecular modeling, and CD exciton coupling analysis, it was determined that the favored enantiomer was 13'(R). Three low-energy conformers of the 13'(S) model were found with MMFF/DFT and were used to calculate the CD spectrum of the ATR dimer (DeVoe method). The Boltzmann weighted spectrum was found to exhibit a positive exciton couplet, in excellent agreement with the experimental spectrum for the first eluted enantiomer. This further suggested that despite the large energy difference between the two interacting chromophores, the dominant source of optical activity in the CD spectrum is the nondegenerate exciton mechanism.

References

Dec 9, 1998·Proceedings of the National Academy of Sciences of the United States of America·C A ParishJ Sparrow
Jun 15, 2000·Proceedings of the National Academy of Sciences of the United States of America·N L MataG H Travis
Jan 5, 2002·The Journal of Biological Chemistry·Shimon Ben-ShabatJanet R Sparrow
Aug 21, 2003·Organic & Biomolecular Chemistry·Nathan FishkinKoji Nakanishi

❮ Previous
Next ❯

Citations

May 3, 2005·Experimental Eye Research·Janet R Sparrow, Mike Boulton
Sep 24, 2010·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Janet R SparrowJilin Zhou
May 5, 2005·Proceedings of the National Academy of Sciences of the United States of America·Nathan E FishkinKoji Nakanishi
Dec 1, 2007·Proceedings of the National Academy of Sciences of the United States of America·So R KimJanet R Sparrow
May 30, 2009·The Journal of Biological Chemistry·Yalin WuJanet R Sparrow
Jan 5, 2008·Photochemistry and Photobiology·Jilin ZhouJanet R Sparrow
Apr 17, 2008·The Journal of Clinical Investigation·Mariacarmela AlloccaAlberto Auricchio
Aug 12, 2009·Journal of Lipid Research·Janet R SparrowJilin Zhou
Aug 6, 2008·Bioorganic & Medicinal Chemistry·Bennie J BenchCoran M H Watanabe
Oct 6, 2009·Vision Research·So Ra KimJanet R Sparrow
Nov 17, 2011·Progress in Retinal and Eye Research·Jennifer J HunterDavid R Williams
Nov 9, 2010·Molecular BioSystems·Bennie J BenchCoran M H Watanabe
Jun 10, 2016·Journal of the American Society for Mass Spectrometry·Neville J A CoughlanEvan J Bieske
Dec 7, 2018·Molecular Diversity·Abdolali AlizadehLong-Guan Zhu
Jun 22, 2017·Chirality·Gennaro Pescitelli, Lorenzo Di Bari

❮ 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.