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Title: Crystal structure of N-{N-[N-acetyl-(S)-leucyl]-(S)-leucyl}norleucinal (ALLN), an inhibitor of proteasome

Journal Article · · Acta Crystallographica. Section E, Crystallographic Communications
 [1];  [1];  [2];  [2]
  1. Peptides International, Inc., Louisville, KY (United States)
  2. Argonne National Lab. (ANL), Argonne, IL (United States)

The title compound, C20H37N3O4, also known by the acronym ALLN, is a tripeptidic inhibitor of the proteolytic activity of the proteasomes, enzyme complexes implicated in several neurodegenerative diseases and other disorders, including cancer. Thus, the crystal structure of ALLN, solved from synchrotron radiation diffraction data, revealed the molecules in extended conformation of the backbone and engaging all peptide N and O atoms in intermolecular hydrogen bonds forming an infinite antiparallel β-sheet.

Research Organization:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Organization:
USDOE
Grant/Contract Number:
AC02-06CH11357; W-31-109-ENG-38
OSTI ID:
1225201
Journal Information:
Acta Crystallographica. Section E, Crystallographic Communications, Vol. 71, Issue 3; ISSN 2056-9890
Publisher:
International Union of CrystallographyCopyright Statement
Country of Publication:
United States
Language:
English

References (18)

20S Proteasome and Its Inhibitors:  Crystallographic Knowledge for Drug Development journal March 2007
Cyclodextrins as templates for the presentation of protease inhibitors journal August 1996
Proteasome Structure, Function, and Lessons Learned from Beta-Lactone Inhibitors journal December 2011
Dysfunction of the ubiquitin-proteasome system in multiple disease conditions: therapeutic approaches journal November 2008
A short history of SHELX journal December 2007
WinGX and ORTEP for Windows : an update journal July 2012
Proteasome Inhibitors: Recent Advances and New Perspectives In Medicinal Chemistry journal February 2010
Stereochemical Criteria for Polypeptide and Protein Chain Conformations journal November 1965
Structure of 20S proteasome from yeast at 2.4Å resolution journal April 1997
Calpains: Attractive Targets for the Development of Synthetic Inhibitors journal February 2010
United States Food and Drug Administration Approval Summary: Bortezomib for the Treatment of Progressive Multiple Myeloma after One Prior Therapy journal May 2006
Inhibition of the Ubiquitin-Proteasome System by Natural Products for Cancer Therapy journal February 2010
Development of proteasome inhibitors as research tools and cancer drugs journal November 2012
Multiparametric scaling of diffraction intensities journal April 2003
Proteasome Inhibitors: An Expanding Army Attacking a Unique Target journal January 2012
Covalent complexes of proteasome model with peptide aldehyde inhibitors MG132 and MG101: docking and molecular dynamics study journal May 2009
STEREOCHEMICAL CRITERIA FOR POLYPEPTIDE AND PROTEIN CHAIN CONFORMATIONS.: VIII. Energy Maps for a Pair of Non-Planar Peptide Units Having Distortion of Bond Angle at the α-Carbon Atom* journal March 1972
20S Proteasome and Its Inhibitors: Crystallographic Knowledge for Drug Development journal May 2007

Cited By (2)

Ceramide Induces the Death of Retina Photoreceptors Through Activation of Parthanatos journal November 2018
The Toxic Effect of ALLN on Primary Rat Retinal Neurons journal May 2016


Figures / Tables (5)