Literature DB >> 18406613

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

Benjamin Amorelli1, Chunhua Yang, Brian Rempel, Stephen G Withers, Spencer 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.

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Year:  2008        PMID: 18406613     DOI: 10.1016/j.bmcl.2008.03.067

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  5 in total

1.  The first crystal structure of a family 129 glycoside hydrolase from a probiotic bacterium reveals critical residues and metal cofactors.

Authors:  Mayo Sato; Dorothee Liebschner; Yusuke Yamada; Naohiro Matsugaki; Takatoshi Arakawa; Siobhán S Wills; Mitchell Hattie; Keith A Stubbs; Tasuku Ito; Toshiya Senda; Hisashi Ashida; Shinya Fushinobu
Journal:  J Biol Chem       Date:  2017-05-25       Impact factor: 5.157

2.  OGA inhibition by GlcNAc-selenazoline.

Authors:  Eun Ju Kim; Dona C Love; Etzer Darout; Mohannad Abdo; Brian Rempel; Stephen G Withers; Paul R Rablen; John A Hanover; Spencer Knapp
Journal:  Bioorg Med Chem       Date:  2010-08-11       Impact factor: 3.641

3.  sp2-Iminosugars targeting human lysosomal β-hexosaminidase as pharmacological chaperone candidates for late-onset Tay-Sachs disease.

Authors:  Manuel González-Cuesta; Irene Herrera-González; M Isabel García-Moreno; Roger A Ashmus; David J Vocadlo; José M García Fernández; Eiji Nanba; Katsumi Higaki; Carmen Ortiz Mellet
Journal:  J Enzyme Inhib Med Chem       Date:  2022-12       Impact factor: 5.756

4.  Crystal structures of a glycoside hydrolase family 20 lacto-N-biosidase from Bifidobacterium bifidum.

Authors:  Tasuku Ito; Takane Katayama; Mitchell Hattie; Haruko Sakurama; Jun Wada; Ryuichiro Suzuki; Hisashi Ashida; Takayoshi Wakagi; Kenji Yamamoto; Keith A Stubbs; Shinya Fushinobu
Journal:  J Biol Chem       Date:  2013-03-11       Impact factor: 5.157

5.  Mechanism of Human Nucleocytoplasmic Hexosaminidase D.

Authors:  Matthew G Alteen; Verena Oehler; Ivana Nemčovičová; Iain B H Wilson; David J Vocadlo; Tracey M Gloster
Journal:  Biochemistry       Date:  2016-05-05       Impact factor: 3.162

  5 in total

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