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Bengt Erik Haug's picture

Bengt Erik Haug

Professor
  • E-mailBengt-Erik.Haug@uib.no
  • Phone+47 55 58 34 68
  • Visitor Address
    Realfagbygget, Allégt. 41
    Room 
    3008
  • Postal Address
    Postboks 7803
    5020 BERGEN

We are interested in research questions that lie on the interface of chemistry and biology. The research projects that we are involved in are rooted within medicinal chemistry and biological chemistry, and we apply synthetic organic chemistry to address our research questions. A fair number of our projects also require access to synthetic peptides, and the group has established and runs the Peptide synthesis laboratory at the Department of Chemistry.

Academic article
  • Show author(s) 2020. Unequivocal structure confirmation of a breitfussin analog by anisotropic NMR measurements. Chemical Science. 12081-12088.
  • Show author(s) 2020. Total synthesis of phorbazole B. Molecules. 1-10.
  • Show author(s) 2019. Kinase chemodiversity from the Arctic: the breitfussins. Journal of Medicinal Chemistry. 10167-10181.
  • Show author(s) 2018. Structural determinants and cellular environment define processed actin as the sole substrate of the N-terminal acetyltransferase NAA80. Proceedings of the National Academy of Sciences of the United States of America. 4405-4410.
  • Show author(s) 2018. Aldol condensations on a 3-alkylidene-2,5-diketopiperazine - synthesis of two marine natural products. Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry. 1303-1306.
  • Show author(s) 2017. Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism. Tetrahedron. 3866-3877.
  • Show author(s) 2017. Oncolytic peptide LTX-315 induces an immune-mediated abscopal effect in a rat sarcoma model. Oncoimmunology. 1-13.
  • Show author(s) 2017. LTX-315: a first-in-class oncolytic peptide that reprograms the tumor microenvironment. Future Medicinal Chemistry. 1339-1344.
  • Show author(s) 2017. Influence of chain length on the activity of tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4). Bioorganic & Medicinal Chemistry. 646-657.
  • Show author(s) 2016. Discovery of a 9-mer cationic peptide (LTX-315) as a potential first in class oncolytic peptide. Journal of Medicinal Chemistry. 2918-2927.
  • Show author(s) 2016. Crystal structure of the Golgi-associated human N-alpha acetyltransferase 60 (Naa60/NatF) reveals the molecular determinants for substrate-specific acetylation. Structure. 1044-1056.
  • Show author(s) 2015. Pseudoaeruginosins, nonribosomal peptides in nodularia spumigena. ACS Chemical Biology. 725-733.
  • Show author(s) 2015. Probing the molecular interactions between CXC chemokine receptor 4 (CXCR4) and an arginine-based tripeptidomimetic antagonist (KRH-1636). Journal of Medicinal Chemistry. 8141-8153.
  • Show author(s) 2015. Discovery of a Specific Inhibitor of Pyomelanin Synthesis in Legionella pneumophila. Journal of Medicinal Chemistry. 8402-8412.
  • Show author(s) 2015. A concise total synthesis of breitfussin A and B. Organic Letters. 122-125.
  • Show author(s) 2014. Reversible ketomethylene-based inhibitors of human neutrophil proteinase 3. Journal of Medicinal Chemistry. 9396-9408.
  • Show author(s) 2014. In silico design, synthesis, and assays of specific substrates for proteinase 3: Influence of fluorogenic and charged groups. Journal of Medicinal Chemistry. 1111-1115.
  • Show author(s) 2014. Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4). Bioorganic & Medicinal Chemistry. 4759-4769.
  • Show author(s) 2013. Synthesis and docking of novel piperidine renin inhibitors. Monatshefte für Chemie. 479-494.
  • Show author(s) 2013. Nitroreductase, a near-infrared reporter platform for in vivo time-domain optical imaging of metastatic cancer. Cancer Research. 1276-1286.
  • Show author(s) 2012. The relative spatial positions of tryptophan and cationic residues in helical membrane-active peptides determines their cytotoxicity. Journal of Biological Chemistry. 233-244.
  • Show author(s) 2012. Interaction of local anaesthetic articaine enantiomers with brain lipids: A Langmuir monolayer study. European Journal of Pharmaceutical Sciences. 394-401.
  • Show author(s) 2012. Debenzylation of Functionalized 4-and 5-substituted 1,2,3-fTriazoles. Synthesis (Stuttgart). 2070-2078.
  • Show author(s) 2012. 1,3-Dipolar cycloaddition of benzyl azide to two highly functionalized alkynes. Monatshefte für Chemie. 505-512.
  • Show author(s) 2011. Synthesis of trans-4-Triazolyl-Substituted 3-Hydroxypiperidines. Synthesis (Stuttgart). 749-754.
  • Show author(s) 2011. Intramolecular hydrogen bonding in articaine can be related to superior bone tissue penetration: A molecular dynamics study. Biophysical Chemistry. 18-25.
  • Show author(s) 2008. Synthetic antimicrobial peptidomimetics with therapeutic potential. Journal of Medicinal Chemistry. 4306-4314.
  • Show author(s) 2008. Antimicrobial Peptides with Stability toward Tryptic Degradation. Biochemistry. 3777-3788.
  • Show author(s) 2007. Application of the Suzuki-Miyaura cross-coupling to increase antimicrobial potency generates promising novel antibacterials. Bioorganic & Medicinal Chemistry Letters.
  • Show author(s) 2005. Facile degradative lactonization of Gln-Arg and Gln-Phe hydroxyethylene dipeptide derivatives. Journal of Peptide Research.
  • Show author(s) 2004. Synthesis of a Gln-Phe hydroxyethylene dipeptide isostere. Organic Letters. 4783-4786.
  • Show author(s) 2004. Bulky nonproteinogenic amino acids permit the design of very small and effective cationic antibacterial peptides. Journal of Medicinal Chemistry. 4159-4162.
  • Show author(s) 2003. The Pharmacophore of Short Cationic Antibacterial Peptides. Journal of Medicinal Chemistry. 1567-1570.
  • Show author(s) 2003. Enhanced antitumor activity of 15-residue bovine lactoferricin derivatives containing bulky aromatic amino acids and lipophilic N-terminal modifications. Journal of Peptide Science. 510-517.
  • Show author(s) 2002. Synthesis of a 2-arylsulphonylated tryptophan: the antibacterial activity of bovine lactoferricin peptides containing Trp(2-Pmc). Journal of Peptide Science. 307-313.
  • Show author(s) 2002. Simple parameterization of non-proteinogenic amino acids for QSAR of antibacterial peptides. Journal of Peptide Science. 302-306.
  • Show author(s) 2001. The effects of charge and lipophilicity on the antibacterial activity of undecapeptides derived from bovine lactoferricin. Journal of Peptide Science. 425-432.
  • Show author(s) 2001. The Role of Tryptophan in the Antibacterial Activity of a 15-Residue Bovine Lactoferricin Peptide. Journal of Peptide Science. 190-196.
  • Show author(s) 2001. Important structural features of 15-residue lactoferricin derivatives and methods for improvement of antimicrobial activity. International Journal of Biochemistry and Cell Biology.
  • Show author(s) 2001. Bulky Aromatic Amino Acids Increase the Antibacterial Activity of Bovine Lactoferricin Peptides. Journal of Peptide Science. 425-432.
  • Show author(s) 2000. Fargestoffer i Sopp. Kjemi.
Lecture
  • Show author(s) 2014. Havet - vårt nye medisinskap?
Popular scientific lecture
  • Show author(s) 2016. Peptider, peptidomimetika og legemiddelutvikling.
  • Show author(s) 2013. Hvordan lager man legemiddelmolekyler?
  • Show author(s) 2012. The Nobel Prize in Chemistry 2012.
  • Show author(s) 2012. Peptider og legemiddelutvikling.
  • Show author(s) 2012. Hvordan lager man et legemiddel?
  • Show author(s) 2007. Antimikrobielle peptider - En kilde til utvikling av fremtidenslegemidler mot mikrober og kreft?
Academic lecture
  • Show author(s) 2020. Synthesis and Biological Activity of the Breitfussins.
  • Show author(s) 2016. Discovery of LTX-315 - A potential first-in-class oncolytic peptide.
  • Show author(s) 2016. BIOSNet - From marine natural products to commercial leads.
  • Show author(s) 2015. Total synthesis of breitfussin A and B.
  • Show author(s) 2014. Design and synthesis of substrates and inhibitors for Proteinase 3.
  • Show author(s) 2014. Design and synthesis of ketomethylene-based inhibitors of human neutrophil Proteinase 3.
  • Show author(s) 2012. Synthesis of piperidine derivatives.
  • Show author(s) 2012. Novel Renin Inhibitors.
  • Show author(s) 2012. Hvordan lager man et legemiddel?
  • Show author(s) 2010. [3+2] Cycloaddition of benzyl azide to two highly functionalized alkynes.
  • Show author(s) 2009. Synthesis of biologically active peptides and peptidomimetics.
  • Show author(s) 2006. Synthesis of a Gln-Phe hydroxyethylene dipeptide isostere.
  • Show author(s) 2001. Antibacterial Activity of 15-Residues Bovine Lactoferricin Derivatives Employing non-coded Aromatic Amino Acids, Peptides 2000.
  • Show author(s) 2000. Increased Antibacterial activity of 15-residues Bovine Lactoferricin Derivatives employing non-coded Aromatic Amino Acids,.
Other product
  • Show author(s) 2001. Antimicrobial compounds and formulations.
Compendium
  • Show author(s) 2010. IUPAC ICOS-18 Proceedings.
Popular scientific article
  • Show author(s) 2001. FARGESTOFFER I SOPP. Blekksoppen. 16-19.
Doctoral dissertation
  • Show author(s) 2016. Synthesis of Bicyclic CXCR4 Antagonists .
  • Show author(s) 2014. Synthesis of serine protease inhibitors.
  • Show author(s) 2012. Synthesis of novel renin inhibitors.
  • Show author(s) 2012. Synthesis of Some Nitrogen Heterocycles of Medicinal Relevance.
Abstract
  • Show author(s) 2012. Synthesis and docking of 4-triazolyl substituted piperidine derivatives as novel renin inhibitors. Journal of Peptide Science. S125-S125.
  • Show author(s) 2011. SAR and Binding Mode for CXCR4 Antagonists Based on an Arg-Arg-Nal Tripeptide Motif. Biopolymers. 492-492.
Poster
  • Show author(s) 2020. Inhibition of the Actin N-terminal acetyltransferase NAA80.
  • Show author(s) 2018. naa10 knockdown and NatA inhibition point to role for the NatA complex in zebrafish dorsoventral axis formation .
  • Show author(s) 2018. Inhibition of the Actin N-terminal acetyltransferase NAA80.
  • Show author(s) 2017. Synthesis of the natural product (3Z,6Z)-3-((1H-imidazol-5-yl)methylene)-6-(2-methylpropylidene)-piperazine-2,5-dione.
  • Show author(s) 2017. Halogenation of electron rich heterocycles: Where does it go?
  • Show author(s) 2016. Total Synthesis of Breitfussin A and B.
  • Show author(s) 2016. Synthesis of a Challenging Amide.
  • Show author(s) 2016. Synthesis of Analogues of the Bioactive Compound Barettin.
  • Show author(s) 2016. Scaffold-based tripeptidomimetic CXCR4 antagonists.
  • Show author(s) 2015. Synthetic studies towards peptidomimetic CXCR4 antagonists.
  • Show author(s) 2015. Synthetic studies towards nitroreductase-activated fluorescent probes.
  • Show author(s) 2015. Synthetic studies towards CXCR4 antagonists.
  • Show author(s) 2014. Synthetic studies towards CXCR4 antagonists.
  • Show author(s) 2014. Synthetic studies towards CXCR4 antagonists.
  • Show author(s) 2014. Synthesis and biological evaluation of pseudopeptide inhibitors of Proteinase 3.
  • Show author(s) 2012. Synthesis of a Ketomethylene Dipeptide Isostere.
  • Show author(s) 2012. Synthesis and docking of 4-triazolyl substituted piperidine derivatives as novel renin inhibitors.
  • Show author(s) 2012. Local Anesthetic Articaine Enantiomers interaction with Brain Lipids.
  • Show author(s) 2011. Synthesis of 3,4-disubstituted piperidines.
  • Show author(s) 2011. Synthesis of 3,4-disubstituted piperidines.
  • Show author(s) 2009. Cycloaddition with highly functionalized terminal alkynes.
  • Show author(s) 2006. Novel Antibacterial Tripeptides.
  • Show author(s) 2001. Preparation of (2S)-3-amino-(2,2,5,7,8-pentamethyl-chroman-6-sulfonyl)-1H-indol-3-yl)-propionic acid and its incorporation into antibacterial lactoferricin peptides.
Academic literature review
  • Show author(s) 2015. Progress toward rationally designed small-molecule peptide and peptidomimetic CXCR4 antagonists. Future Medicinal Chemistry. 1261-1283.
  • Show author(s) 2007. The medicinal chemistry of short lactoferricin-based antibacterial peptides. Current Medicinal Chemistry. 1-18.

More information in national current research information system (CRIStin)

Targeting novel antibacterial targets

The group in involved in several research projects where novel targets for future antibiotics are investigated. Our focus is on processes that are essential in bacteria and in our work we address several different riboswitches, which are non-codning structural elements in mRNA that regulate gene expression by binding to small organic molecules, in addition to key enzymes in the fatty acid synthesis machinery in bacteria.

Early drug discovery

The group is partner in the RESPOND3 project on responsible early digital drug discovery within the Centre for Digital Life Norway. This project focuses on developing better computational approaches and responsible innovation strategies in early drug discovery with applications to antibiotics and COPD.

 

Molecular imaging

The group is part of the Tracer Development Center of the Norwegian Nuclear Medicine Consortium.

 

Inhibitors of N-terminal acetyl transferases

Proteins constitute an essential part of the machinery of life and display enormous variation in both structure and function. In addition to the diversity inferred by the 20 coded amino acids, proteins are often covalently modified during or after biosynthesis, which adds additional layers of complexity.

Acetylation is one of the most common co- or post-translational protein modifications, and occurs either on the amino group of lysine side chains (K-acetylation) or on the alpha-amino group of N-terminal residues (Nt-acetylation).

Nt-acetylation of proteins is extremely common and occurs on more than 80% of all human proteins. Biochemically it consists of transfer of an acetyl group from acetyl coenzyme A (Ac-CoA) to the protein substrate and is catalysed by the N-terminal acetyltransferase (NAT) group of enzymes.

Although our understanding of the NATs has increased in recent years, there are fundamental questions that remain unanswered in the field:
- What are the cellular roles of NAT enzymes (and thus Nt-acetylation)?
- Can NATs be targeted for therapeutic intervention in cancer and other diseases? 

Access to specific and potent NAT inhibitors is a prerequisite to answer these questions, and we are working toward equipping the scientific community with these molecular tools.