August 2011 – Page 2 – Organic & Biomolecular Chemistry Blog

Archive for August, 2011

HOT: Using precursor-directed biosynthesis to open new fronts in the battle against cancer

11 Aug 2011

Supplying an organism with modified precursor materials for biosynthesis is a great way of hijacking the synthetic machinery of an organism to make the compounds you want. In this paper Cormac Murphy and colleagues from University College Dublin and Ecole Normale Superieure demonstrate that precursor-directed biosynthesis is a convenient way to create analogs of rumbrin with tunable potency and selectivity, also showing that the 3-chloropyrrole moiety is not absolutely essential for biological activity in this class of polyenes. One of the compounds prepared showed dramatically improved activity against lung cancer cells.

Interested? Read this article in OBC, it is free to access for the next four weeks!

Production of anticancer polyenes through precursor-directed biosynthesis
Benjamin R. Clark, Stephen O’Connor, Deirdre Fox, Jacques Leroy and Cormac D. Murphy
Org. Biomol. Chem., 2011, Advance Article

DOI: 10.1039/C1OB05667K

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Review: Glycoconjugates degradation – the enzymes involved and their probes

09 Aug 2011

Glycoconjugates play a major role in a number of biological processes, for example modulating cellular interactions, and chemical tools have been instrumental in understanding these aspects of the glycosciences.

In this OBC Perspective Herman Overkleeft and co-authors provide an overview of the enzymes involved in the degradation of glycoconjugates, and the activity-based probes that have been used to study these enzymes, along with the advantages and disadvantages of these probes. Addressing all facets of carbohydrate enzymology, the authors identify a number of key areas for future development in the field.

Are you a glycoscientist or a bioorganic chemist? Then this OBC Perspective is for you! Download the article to read the full details:
Irreversible inhibitors and activity-based probes as research tools in chemical glycobiology
Martin D. Witte, Gijsbert A. van der Marel, Johannes M. F. G. Aerts and Herman S. Overkleeft
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05531C, Perspective

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HOT: Novel drugs fight back against MRSA

05 Aug 2011

The enormous success of antibiotics is seriously threatened by the development of resistance to many drugs available on the market. So the search for new antibiotics that are less prone to resistance is on.

Antimicrobial peptides (AMPs) are a possible solution that has attracted considerable attention but they have some drawbacks including high cost of manufacturing. Now Steven Firestine and colleagues at Wayne State University in the US have examined the potential of a new class of benzophenone-based membrane targeted antibiotics (BPMTAs).

Firestine shows that these agents release potassium ions from treated bacteria which results in disruption of the bacterial membrane potential. This membrane-targeted disruption means that BPMTAs have excellent activity against antibiotic-resistant strains like MRSA and VRSA.

The team have demonstrated the promising potential of these agents by using them to cure mice of a lethal MRSA infection. They were also unable to develop a mutant resistant to the agents.

Interested? Read the article in OBC that is free to access for the next four weeks!

Examination of a synthetic benzophenone membrane-targeted antibiotic
Sunil K. Vooturi, Mahender B. Dewal and Steven M. Firestine
Org. Biomol. Chem., 2011, DOI: 10.1039/C1OB05643C

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RCM synthesis of amphidinolactone A core on the cover of Issue 16

05 Aug 2011

On the front cover of this issue is work from Debendra Mohapatra at the Indian Institute of Chemical Technology, together with colleagues at Hyderabad University and King Saud University on the ring-closing metathesis based synthesis of the macrolactone core of amphidinolactone A.

The convergent synthesis achieved the macrolactone core in 32% yield and demonstrated the steric hinderance resulting from protecting groups in the RCM reaction. PMB (p-methoxybenzyl ether) protecting groups on the macrolactonization precursor prevented the RCM reaction from proceeding, but simple de-protection to the subsequent diol achieved the 13-membered lactone ring system present in amphidinolactone A in 76% yield. Further work to incorporate the the RCM reaction into the total synthesis of amphidinolactone A is ongoing.

Ring-closing metathesis (RCM) based synthesis of the macrolactone core of amphidinolactone A
Debendra K. Mohapatra, Manas R. Pattanayak, Pragna P. Das, Tapas R. Pradhan and J. S. Yadav
Org. Biomol. Chem., 2011,
DOI: 10.1039/C1OB05335C

View the rest of the articles in Issue 16

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Organic & Biomolecular Chemistry Blog

Archive for August, 2011

HOT: Using precursor-directed biosynthesis to open new fronts in the battle against cancer

Review: Glycoconjugates degradation – the enzymes involved and their probes

HOT: Novel drugs fight back against MRSA

RCM synthesis of amphidinolactone A core on the cover of Issue 16

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