Literature DB >> 3643025

The Lossen rearrangement in biological systems. Inactivation of leukocyte elastase and alpha-chymotrypsin by (dl)-3-benzyl-N-(methanesulfonyloxy) succinimide.

W C Groutas, P K Giri, J P Crowley, J C Castrisos, M J Brubaker.   

Abstract

(dl)-3-Benzyl-N-(methanesulfonyloxy) succinimide 5 has been found to inactivate human leukocyte elastase and alpha-chymotrypsin efficiently and irreversibly. The kobsd/[I] values were 1170 and 9000 M-1 s-1 respectively. Porcine pancreatic elastase was not inhibited by 5. Compound 5 may constitute the first example of a mechanism-based inhibitor of a serine proteinase that appears to exert its effect via an unprecedented enzyme-induced Lossen rearrangement.

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Year:  1986        PMID： 3643025     DOI： 10.1016/s0006-291x(86)80235-2

Source DB:  PubMed          Journal:  Biochem Biophys Res Commun        ISSN： 0006-291X            Impact factor:   3.575


  5 in total

1.  Novel histone deacetylase 8 ligands without a zinc chelating group: exploring an 'upside-down' binding pose.

Authors:  Aditya Sudheer Vaidya; Raghupathi Neelarapu; Antonett Madriaga; He Bai; Emma Mendonca; Hazem Abdelkarim; Richard B van Breemen; Sylvie Y Blond; Pavel A Petukhov
Journal:  Bioorg Med Chem Lett       Date:  2012-09-07       Impact factor: 2.823

2.  Why Hydroxamates May Not Be the Best Histone Deacetylase Inhibitors--What Some May Have Forgotten or Would Rather Forget?

Authors:  Sida Shen; Alan P Kozikowski
Journal:  ChemMedChem       Date:  2015-11-25       Impact factor: 3.466

3.  Assessment of the trifluoromethyl ketone functionality as an alternative zinc-binding group for selective HDAC6 inhibition.

Authors:  Yves Depetter; Silke Geurs; Flore Vanden Bussche; Rob De Vreese; Jorick Franceus; Tom Desmet; Olivier De Wever; Matthias D'hooghe
Journal:  Medchemcomm       Date:  2018-05-18       Impact factor: 3.597

4.  Lossen Rearrangement of p-Toluenesulfonates of N-Oxyimides in Basic Condition, Theoretical Study, and Molecular Docking.

Authors:  Monika Kijewska; Abeer A Sharfalddin; Łukasz Jaremko; Marta Cal; Bartosz Setner; Miłosz Siczek; Piotr Stefanowicz; Mostafa A Hussien; Abdul-Hamid Emwas; Mariusz Jaremko
Journal:  Front Chem       Date:  2021-04-15       Impact factor: 5.221

5.  One-pot efficient synthesis of N(α)-urethane-protected β- and γ-amino acids.

Authors:  Marta Cal; Mariusz Jaremko; Łukasz Jaremko; Piotr Stefanowicz
Journal:  Amino Acids       Date:  2012-12-19       Impact factor: 3.520
  5 in total

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