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  5. Engineered biosynthesis and characterisation of disaccharide-modified 8-deoxyamphoteronolides
 
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Engineered biosynthesis and characterisation of disaccharide-modified 8-deoxyamphoteronolides

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Download Caffrey_Walmsley_AMAB_D_16_02148_accepted_manuscript.pdf330.72 KB
Download Caffrey_Walmsley_AMAB_D_16_02148_supplementary_information.pdf572.5 KB
Author(s)
Walmsley, Simon 
De Poire, Eimear 
Rawlings, Bernard 
Caffrey, Patrick 
Uri
http://hdl.handle.net/10197/8286
Date Issued
March 2017
Date Available
17T02:00:10Z November 2017
Abstract
Several polyene macrolides are potent antifungal agents that have severe side effects. Increased glycosylation of these compounds can improve water solubility and reduce toxicity. Three extending glycosyltransferases are known to add hexoses to the mycosaminyl sugar residues of polyenes. The Actinoplanes caeruleus PegA enzyme catalyses attachment of a D-mannosyl residue in a β-1,4 linkage to the mycosamine of the aromatic heptaene 67-121A to form 67-121C. NppY from Pseudonocardia autotrophica adds an N-acetyl-D-glucosamine to the mycosamine of 10-deoxynystatin. NypY from Pseudonocardia sp. P1 adds an extra hexose to a nystatin, but the identity of the sugar is unknown. Here, we express the nypY gene in Streptomyces nodosus amphL and show that NypY modifies 8-deoxyamphotericins more efficiently than C-8 hydroxylated forms. The modified heptaene was purified and shown to be mannosyl-8-deoxyamphotericin B. This had the same antifungal activity as amphotericin B but was slightly less haemolytic. Chemical modification of this new disaccharide polyene could give better antifungal antibiotics.
Sponsorship
Science Foundation Ireland
Type of Material
Journal Article
Publisher
Springer
Journal
Applied Microbiology and Biotechnology
Volume
101
Issue
5
Start Page
1899
End Page
1905
Copyright (Published Version)
2016 Springer
Keywords
  • Streptomyces nodosus

  • Glycosyltransferases

  • Amphotericin disaccha...

DOI
10.1007/s00253-016-7986-6
Language
English
Status of Item
Peer reviewed
This item is made available under a Creative Commons License
https://creativecommons.org/licenses/by-nc-nd/3.0/ie/
Owning collection
Biomolecular and Biomedical Science Research Collection
Scopus© citations
6
Acquisition Date
Jan 25, 2023
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1256
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Acquisition Date
Jan 26, 2023
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Acquisition Date
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