Synthetic Phosphodiester-Linked 4-Amino-4-deoxy-l-arabinose Derivatives Demonstrate that ArnT is an Inverting Aminoarabinosyl Transferase.
Burkholderia
carbohydrates
glycolipids
glycosyl transferases
lipopolysaccharide
Journal
Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Titre abrégé: Chembiochem
Pays: Germany
ID NLM: 100937360
Informations de publication
Date de publication:
02 12 2019
02 12 2019
Historique:
received:
28
05
2019
pubmed:
25
6
2019
medline:
14
8
2020
entrez:
25
6
2019
Statut:
ppublish
Résumé
4-Amino-4-deoxy-l-arabinopyranose (Ara4N) residues have been linked to antibiotic resistance due to reduction of the negative charge in the lipid A and core regions of the bacterial lipopolysaccharide (LPS). To study the enzymatic transfer of Ara4N onto lipid A, which is catalysed by the ArnT transferase, we chemically synthesised a series of anomeric phosphodiester-linked lipid Ara4N derivatives containing linear aliphatic chains as well as E- and Z-configured monoterpene units. Coupling reactions were based on sugar-derived H-phosphonates, followed by oxidation and global deprotection. The enzymatic Ara4N transfer was performed in vitro with crude membranes from a deep-rough mutant from Escherichia coli as acceptor. Product formation was detected by TLC and LC-ESI-QTOF mass spectrometry. Out of seven analogues tested, only the α-neryl derivative was accepted by the Burkholderia cenocepacia ArnT protein, leading to substitution of the Kdo
Identifiants
pubmed: 31233657
doi: 10.1002/cbic.201900349
pmc: PMC6902282
doi:
Substances chimiques
Amino Sugars
0
Bacterial Proteins
0
Lipid A
0
Organophosphates
0
Organophosphonates
0
4-amino-4-deoxyarabinose
33406-49-4
Pentosyltransferases
EC 2.4.2.-
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
2936-2948Subventions
Organisme : Austrian Science Fund FWF
ID : P 28826_N26
Pays : Austria
Informations de copyright
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
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