Assessing the ability of a short fluorinated antifreeze glycopeptide and a fluorinated carbohydrate derivative to inhibit ice recrystallization

Bioorganic & Medicinal Chemistry Letters
Jennifer L Chaytor, Robert N Ben

Abstract

A short fluorinated antifreeze glycopeptide (2) was synthesized and evaluated for ice recrystallization inhibition (IRI) activity. The activity of 2 was compared to native biological antifreeze AFGP 8 and a rationally designed C-linked AFGP analogue (OGG-Gal, 1). In addition, a simple fluorinated galactose derivative was prepared and its IRI activity was compared to non-fluorinated compounds. The results from this study suggest that the stereochemistry at the anomeric position in the carbohydrate plays a role in imparting ice recrystallization inhibition activity and that incorporation of hydrophobic groups such as fluorine atoms cause a decrease in IRI activity. These observations are consistent with the theory that fluorine atoms increase ordering of bulk water resulting in a decrease of IRI activity, supporting our previously proposed mechanism of ice recrystallization inhibition.

References

Aug 1, 1971·Cryobiology·P F Scholander, J E Maggert
Apr 29, 1994·Biochemical and Biophysical Research Communications·B RubinskyC Y Lee
Nov 14, 1997·Journal of Surgical Oncology·H KoushafarB Rubinsky
Oct 27, 1998·Cryobiology·A A Gage, J Baust
Apr 7, 1999·Cryobiology·L PhamB Rubinsky
Sep 1, 2000·Carbohydrate Research·S J Williams, S G Withers
May 4, 2004·Chembiochem : a European Journal of Chemical Biology·Justin C BiffingerStephen G DiMagno
Mar 15, 2006·Annals of the New York Academy of Sciences·Alex Fowler, Mehmet Toner
Feb 16, 2008·Journal of the American Chemical Society·Pawel CzechuraRobert N Ben
Dec 5, 2008·Journal of the American Chemical Society·Roger Y TamRobert N Ben
Oct 15, 2009·Journal of the American Chemical Society·Roger Y TamRobert N Ben

❮ Previous
Next ❯

Citations

Aug 6, 2011·Bioconjugate Chemistry·Mathieu LeclèreRobert N Ben
Feb 2, 2013·Journal of Medicinal Chemistry·Hannguang ChaoR Michael Lawrence
Apr 13, 2011·Chemistry : a European Journal·Sophie ColombelXavier Pannecoucke
Oct 15, 2011·Nature Biotechnology·Kazuo N Watanabe, Guat Hong Teh
Oct 30, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Indrapal Singh Aidhen, Naveenkumar Thoti

❮ 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.