Directed microbial biosynthesis of deuterated biosurfactants and potential future application to other bioactive molecules

Thomas Smyth, Amedea Perfumo, R Marchant, Ibrahim Banat

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Deuterated rhamnolipids were produced using strain AD7 of Pseudomonas aeruginosa, which was progressively adapted to increasing levels of deuterium in D2O and carbon substrates. Fourteen different deuterated rhamnolipid structures, including structural isomers, were produced which is similar to normal protonated structures. There were two main products monorhamnolipid Rha-C-10-C-10 and dirhamnolipid Rha(2)-C-10-C-10. The levels of deuteration varied from 16% with 25% D2O + h-glycerol to 90% with 100% D2O + d-glycerol. When d-tetradecane was used with H2O, virtually all the deuterium appeared in the lipid chains while using h-tetradecane + D2O led to the majority of deuterium in the sugars. The adaptation to growth in deuterium appeared to be metabolic since no genetic changes could be found in the key rhamnolipid biosynthetic genes, the rhamnosyl transferases RhlB and RhlC. Deuterated sophorolipids were similarly produced using Candida bombicola and Candida apicola although in this case, no adaptation process was necessary. Up to 40 different sophorolipids were produced by these yeasts. However, unlike the rhamnolipids, use of D2O did not lead to any deuteration of the lipid chains, but direct incorporation into the lipid was achieved using d-isostearic acid. The results from these experiments show the feasibility of producing deuterated bioactive compounds from microorganisms coupled with the possibility of manipulating the pattern of labelling through judicious use of different deuterated substrates.
LanguageEnglish
Pages1347-1354
JournalApplied Microbiology and Biotechnology
Volume87
Issue number4
DOIs
Publication statusPublished - Aug 2010

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biosurfactants
deuterium
biosynthesis
sophorolipids
glycerol
lipids
Candida
transferases
Pseudomonas aeruginosa
isomers
rhamnolipids
yeasts
sugars
microorganisms
carbon
acids

Cite this

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abstract = "Deuterated rhamnolipids were produced using strain AD7 of Pseudomonas aeruginosa, which was progressively adapted to increasing levels of deuterium in D2O and carbon substrates. Fourteen different deuterated rhamnolipid structures, including structural isomers, were produced which is similar to normal protonated structures. There were two main products monorhamnolipid Rha-C-10-C-10 and dirhamnolipid Rha(2)-C-10-C-10. The levels of deuteration varied from 16{\%} with 25{\%} D2O + h-glycerol to 90{\%} with 100{\%} D2O + d-glycerol. When d-tetradecane was used with H2O, virtually all the deuterium appeared in the lipid chains while using h-tetradecane + D2O led to the majority of deuterium in the sugars. The adaptation to growth in deuterium appeared to be metabolic since no genetic changes could be found in the key rhamnolipid biosynthetic genes, the rhamnosyl transferases RhlB and RhlC. Deuterated sophorolipids were similarly produced using Candida bombicola and Candida apicola although in this case, no adaptation process was necessary. Up to 40 different sophorolipids were produced by these yeasts. However, unlike the rhamnolipids, use of D2O did not lead to any deuteration of the lipid chains, but direct incorporation into the lipid was achieved using d-isostearic acid. The results from these experiments show the feasibility of producing deuterated bioactive compounds from microorganisms coupled with the possibility of manipulating the pattern of labelling through judicious use of different deuterated substrates.",
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Directed microbial biosynthesis of deuterated biosurfactants and potential future application to other bioactive molecules. / Smyth, Thomas; Perfumo, Amedea; Marchant, R; Banat, Ibrahim.

In: Applied Microbiology and Biotechnology, Vol. 87, No. 4, 08.2010, p. 1347-1354.

Research output: Contribution to journalArticle

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AU - Perfumo, Amedea

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AU - Banat, Ibrahim

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AB - Deuterated rhamnolipids were produced using strain AD7 of Pseudomonas aeruginosa, which was progressively adapted to increasing levels of deuterium in D2O and carbon substrates. Fourteen different deuterated rhamnolipid structures, including structural isomers, were produced which is similar to normal protonated structures. There were two main products monorhamnolipid Rha-C-10-C-10 and dirhamnolipid Rha(2)-C-10-C-10. The levels of deuteration varied from 16% with 25% D2O + h-glycerol to 90% with 100% D2O + d-glycerol. When d-tetradecane was used with H2O, virtually all the deuterium appeared in the lipid chains while using h-tetradecane + D2O led to the majority of deuterium in the sugars. The adaptation to growth in deuterium appeared to be metabolic since no genetic changes could be found in the key rhamnolipid biosynthetic genes, the rhamnosyl transferases RhlB and RhlC. Deuterated sophorolipids were similarly produced using Candida bombicola and Candida apicola although in this case, no adaptation process was necessary. Up to 40 different sophorolipids were produced by these yeasts. However, unlike the rhamnolipids, use of D2O did not lead to any deuteration of the lipid chains, but direct incorporation into the lipid was achieved using d-isostearic acid. The results from these experiments show the feasibility of producing deuterated bioactive compounds from microorganisms coupled with the possibility of manipulating the pattern of labelling through judicious use of different deuterated substrates.

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