Synthesis of a non-natural glucose-2-phosphate ester able to dupe the acc system of Agrobacterium fabrum

Literature Information

Publication Date 2019-01-04
DOI 10.1039/C8OB03086C
Impact Factor 3.876
Authors

Si-Zhe Li, Armelle Vigouroux, Mohammed Ahmar, Abbas El Sahili, Laurent Soulère, Laïla Sago, David Cornu, Solange Moréra, Yves Queneau


View Original

Abstract

The first non-natural derivative of the rare D-glucose-2-phosphate (G2P), namely glucose-2-(O-lactic acid phosphate) (G2LP), has been synthesized. When used as sole carbon source, G2LP enables bacterial growth of the plant pathogenic strain Agrobacterium fabrum C58 (formerly referred to as Agrobacterium tumefaciens). X-ray crystallography and affinity measurements investigations reveal that G2LP binds the periplasmic binding protein (PBP) AccA similarly to the natural compounds and with the same affinity. Moreover, enzymatic assays show that it is able to serve as substrate of the phosphodiesterase AccF. The properties found for G2LP demonstrate that the very unusual glucose-2-phosphoryl residue, present in G2LP, can be used as structural feature for designing non-natural systems fully compatible with the Acc cascade of A. fabrum.

Related Literature

From atactic to isotactic CO/p-methylstyrenecopolymer by proper modification of Pd(ii) catalysts bearing achiral α-diimines

Barbara Binotti, Carla Carfagna, Cristiano Zuccaccia, Alceo Macchioni

2004-11-29 Communication

DOI: 10.1039/B411214H

Total synthesis of (+)-belactosin A

Alan Armstrong, James N. Scutt

2004-01-27 Communication

DOI: 10.1039/B316142K

Photon-driven nanomechanical cyclic motion

Hai-Feng Ji, Yu Feng, Xiaohe Xu, Vemana Purushotham, Thomas Thundat, Gilbert M. Brown

2004-09-28 Communication

DOI: 10.1039/B408997A

Gold and silver nanoparticles functionalized with known numbers of oligonucleotides per particle for DNA detection

Yang Chen, Jenny Aveyard, Robert Wilson

2004-11-18 Communication

DOI: 10.1039/B411181H

Dispersing palladium nanoparticles using a water-in-oil microemulsion—homogenization of heterogeneous catalysis

Byunghoon Yoon, Hakwon Kim, Chien M. Wai

2003-04-02 Communication

DOI: 10.1039/B211836J

Palladium catalysed cyclisation–carbonylation of enynes to give cyclic γ,δ-unsaturated acids

Varinder K. Aggarwal, Mike Butters, Paul W. Davies

2003-04-02 Communication

DOI: 10.1039/B300719G

In situ magnetic resonance imaging of electrically-induced water diffusion in a Nafion ionic polymer film

Richard T. Baker, Leila Naji, Karen Lochhead, John A. Chudek

2003-03-18 Communication

DOI: 10.1039/B301039B

Modified micro-space using self-organized nanoparticles for reduction of methylene blue

Xianying Li, Hongzhi Wang, Kouzou Inoue, Masato Uehara, Hiroyuki Nakamura, Masaya Miyazaki, Eiichi Abe, Hideaki Maeda

2003-03-18 Communication

DOI: 10.1039/B300765K

NMR and ion selective electrode studies of hydraphile channels correlate with biological activity in E. coli and B. subtilis

W. Matthew Leevy, Michelle E. Weber, Paul H. Schlesinger

2004-11-25 Communication

DOI: 10.1039/B413588A

You might also like

Compound Q&A

What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?

(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...

16326-97-9(1R,3S)-1,3-Cyclopen...
Compound Q&A

What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?

When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...

637-31-0N'-[4-(Dimethylamino...
Compound Q&A

Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?

There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...

1352318-16-15-(2,4-Difluoropheny...
Compound Q&A

What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?

1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...

382141-68-61-(3-Methoxyphenoxy)...
Compound Q&A

Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?

Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...

18660-81-6Tetrodotoxin Citrate
Compound Q&A

What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?

2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...

225641-84-92-Methyl-2-propanyl ...
Compound Q&A

How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?

Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...

16261-80-64-(2-Hydroxyhexafluo...
Compound Q&A

How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?

2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...

102507-19-72-Methyl-2-propanyl ...
Compound Q&A

What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?

Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...

20735-15-3Benzeneethanamine, α...
Compound Q&A

Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?

In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...

20691-84-33-{(E)-[4-(Dimethyla...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.