Synthesis of a non-natural glucose-2-phosphate ester able to dupe the acc system of Agrobacterium fabrum
Literature Information
Si-Zhe Li, Armelle Vigouroux, Mohammed Ahmar, Abbas El Sahili, Laurent Soulère, Laïla Sago, David Cornu, Solange Moréra, Yves Queneau
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.
Recommended Journals

Critical Reviews in Solid State and Materials Sciences

Atomization and Sprays

Medicinal Chemistry Research

Topics in Catalysis

Polycyclic Aromatic Compounds

Bioorganic & Medicinal Chemistry

Heteroatom Chemistry

Journal of Asian Natural Products Research

Journal of the Indian Institute of Science

Bioorganic & Medicinal Chemistry Letters
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
DOI: 10.1039/B411214H
Total synthesis of (+)-belactosin A
Alan Armstrong, James N. Scutt
DOI: 10.1039/B316142K
Photon-driven nanomechanical cyclic motion
Hai-Feng Ji, Yu Feng, Xiaohe Xu, Vemana Purushotham, Thomas Thundat, Gilbert M. Brown
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
DOI: 10.1039/B411181H
Dispersing palladium nanoparticles using a water-in-oil microemulsion—homogenization of heterogeneous catalysis
Byunghoon Yoon, Hakwon Kim, Chien M. Wai
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
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
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
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
DOI: 10.1039/B413588A
Chemistry of materials under extreme high pressure-high-temperature conditions
DOI: 10.1039/B300963G
You might also like
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...
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...
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 ...
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...
Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?
Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...
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...
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) ...
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...
What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?
Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...
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...
Source Journal
Organic & Biomolecular Chemistry

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.




![N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide structure N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide structure](https://static.chemtradehub.com/structs/480/480452-37-7-0898.webp)