N-Acetylhexosaminidase inhibitory properties of C-1 homologated GlcNAc- and GalNAc-thiazolines

Bioorganic & Medicinal Chemistry Letters
Benjamin AmorelliSpencer Knapp

Abstract

Several C-1 homologated GlcNAc- and GalNAc-thiazolines, as well as a related GalNAc-thiazole, have been prepared. The compounds are analogues of GlcNAc-thiazoline, a potent transition-state-mimicking inhibitor of retaining beta-N-acetylglycosaminidases. Kinetic evaluation of these fused pyranose-heterocycles against the bacterial N-acetylhexosaminidase SpHex suggests active site steric restrictions around the substrate anomeric carbon.

References

Apr 15, 1973·Science·G E Lienhard
Aug 16, 1969·Nature·R Wolfenden
Jan 2, 2001·The Journal of Biological Chemistry·B L MarkM N James
May 12, 2001·The Journal of Organic Chemistry·S Knapp, D S Myers
Sep 5, 2001·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·J A Hanover
Apr 27, 2002·The Journal of Organic Chemistry·Spencer Knapp, David S Myers
Dec 21, 2006·Journal of the American Chemical Society·Helge C DorfmuellerDaan M F van Aalten
Mar 28, 2007·Journal of the American Chemical Society·Jacqueline WickiStephen G Withers
May 19, 2007·Organic Letters·Spencer KnappJohn A Hanover

❮ Previous
Next ❯

Citations

Mar 25, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jana KrejzováVladimír Křen
Mar 13, 2013·The Journal of Biological Chemistry·Tasuku ItoShinya Fushinobu
May 5, 2010·Biotechnology Advances·Kristýna SlámováVladimír Kren
May 29, 2016·Enzyme and Microbial Technology·Jana KrejzováVladimír Křen
May 6, 2016·Biochemistry·Matthew G AlteenTracey M Gloster
Apr 20, 2012·Chembiochem : a European Journal of Chemical Biology·Mitchell HattieKeith A Stubbs
May 7, 2010·The Journal of Organic Chemistry·Ethan D Goddard-Borger, Keith A Stubbs
Sep 9, 2010·Bioorganic & Medicinal Chemistry·Eun Ju KimSpencer Knapp

❮ 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.