Action of atrop‐Abyssomicin C as an Inhibitor of 4‐Amino‐4‐deoxychorismate Synthase PabB

Keller, Simone; Schadt, Heiko S.; Ortel, Ingo; Süssmuth, Roderich D.

doi:10.1002/anie.200701836

Cited by 66 publications

(54 citation statements)

References 23 publications

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“…5) in which the main compound, atrop-abyssomicin C, was active against Gram-positive bacteria, including multiresistant-and vancomycin-resistant-Staphylococcus aureus isolates Bister et al 2004;Keller et al 2007a). All of the abyssomicins mimic the structure of chorismate, the natural substrate for the PabB subunit of 4-amino-4-deoxychorismate synthase, though only abyssomicin C and atropabyssomicin C bind covalently to PabB by a Michael addition mechanism (Keller et al 2007b).…”

Section: Recent Discoveries From Our Research Groupmentioning

confidence: 99%

A guide to successful bioprospecting: informed by actinobacterial systematics

Goodfellow

Fiedler

2010

Antonie van Leeuwenhoek

296

200

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New structurally diverse natural products are discovered when novel screening procedures are introduced or when high quality biological materials from new sources are examined in existing screens, hence it is important to foster these two aspects of novelty in drug discovery programmes. Amongst prokaryotes, actinomycetes, notably streptomycetes, remain a rich source of new natural products though it has become increasingly difficult to find such metabolites from common actinomycetes as screening 'old friends' leads to the costly rediscovery of known compounds. The bioprospecting strategy which is the subject of this review is based upon the premise that new secondary metabolites can be found by screening relatively small numbers of dereplicated, novel actinomycetes isolated from marine sediments. The success of the strategy is exemplified by the discovery of a range of novel bioactive compounds, notably atrop-abyssomicin C and proximicins A, B and C from Verrucosispora strains isolated from sediment samples taken from the Sea of Japan and the Raune Fjord, respectively, and the dermacozines derived from Dermacoccus strains isolated from the Challenger Deep of the Mariana Trench in the Pacific Ocean. The importance of current advances in prokaryotic systematics in work of this nature is stressed and a plea made that resources be sought to train, support and employ the next generation of actinobacterial systematists.

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Section: Recent Discoveries From Our Research Groupmentioning

confidence: 99%

A guide to successful bioprospecting: informed by actinobacterial systematics

Goodfellow

Fiedler

2010

Antonie van Leeuwenhoek

296

200

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“…Atrop-abyssomycin C was shown to inhibit Bacillus subtilis 4-amino-4-deoxychorismate (ADC) synthase (PabB), and covalent modi-cation of an active site cysteine residue was conrmed using mass-spectrometric analysis. 74 Very recently, the structure of abyssomicin J as a thioether-linked abyssomycin dimer (Fig. 4) and its activity against M. tuberculosis was reported.…”

Section: Bioactivities Of Small Spirotetronatesmentioning

confidence: 98%

Recent advances in the field of bioactive tetronates

et al. 2014

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Covering: up to mid-2014 Over the last several decades, the number of pharmacologically active natural products has significantly increased and several natural product families have taken shape. This review highlights the family of tetronate and spirotetronate compounds, which show a vast structural and functional diversity. The rapid growth of this group has created the need for a comprehensive overview and classification system, which we have devised based on structural characteristics. An updated overview is provided based on known tetronates, intended to spur further research in this field by identifying common structural features and general principles of their biosynthesis. We also compare a selection of chemical syntheses of representative compounds belonging to individual subtypes, both in terms of their efficiency as well as the extent to which they are biomimetic. This review also summarizes progress in unraveling some of the principles underlying the potent and varied bioactivities of natural tetronate antibiotics, and in identifying and better understanding their structure–activity relationships and modes of action.DFG, EXC 314, Unifying Concepts in Catalysi

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“…Furthermore, several natural products containing α,β-unsaturated chemotypes are known to bind covalently with proteins, leading to relevant biological responses. [7,8] Examples include the protein kinase inhibitor hypothemycin [7a] and antibacterial agent atrop -abyssomicin C, [7b] which function by covalently binding to a cysteine residue on their targets. Similarly, syringolin A targets the proteasome via Michael addition of a catalytic threonine to the α,β-unsaturated amide.…”

mentioning

confidence: 99%

Modular Synthesis of Novel Macrocycles Bearing α,β‐Unsaturated Chemotypes through a Series of One‐Pot, Sequential Protocols

Javed

Mahipal

Torres

et al. 2016

Chemistry A European J

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A series of one-pot, sequential protocols was developed for the synthesis of novel macrocycles bearing α,β-unsaturated chemotypes. The method highlights a phosphate tether-mediated approach to establish asymmetry, and consecutive one-pot, sequential processes to access the macrocycles with minimal purification procedures. This library amenable strategy provided diverse macrocycles containing α,β-unsaturated carbon-, sulfur- or phosphorus-based warheads.

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Action of atrop‐Abyssomicin C as an Inhibitor of 4‐Amino‐4‐deoxychorismate Synthase PabB

Cited by 66 publications

References 23 publications

A guide to successful bioprospecting: informed by actinobacterial systematics

A guide to successful bioprospecting: informed by actinobacterial systematics

Recent advances in the field of bioactive tetronates

Modular Synthesis of Novel Macrocycles Bearing α,β‐Unsaturated Chemotypes through a Series of One‐Pot, Sequential Protocols

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