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β-Mannanase-catalyzed synthesis of alkyl mannooligosides

Morrill, Johan LU ; Månberger, Anna LU ; Rosengren, Anna LU ; Naidjonoka, Polina LU ; von Freiesleben, Pernille; Krogh, Kristian B.R.M.; Bergquist, Karl Erik LU ; Nylander, Tommy LU ; Karlsson, Eva Nordberg LU and Adlercreutz, Patrick LU , et al. (2018) In Applied Microbiology and Biotechnology 102(12). p.5149-5163
Abstract

β-Mannanases catalyze the conversion and modification of β-mannans and may, in addition to hydrolysis, also be capable of transglycosylation which can result in enzymatic synthesis of novel glycoconjugates. Using alcohols as glycosyl acceptors (alcoholysis), β-mannanases can potentially be used to synthesize alkyl glycosides, biodegradable surfactants, from renewable β-mannans. In this paper, we investigate the synthesis of alkyl mannooligosides using glycoside hydrolase family 5 β-mannanases from the fungi Trichoderma reesei (TrMan5A and TrMan5A-R171K) and Aspergillus nidulans (AnMan5C). To evaluate β-mannanase alcoholysis capacity, a novel mass spectrometry-based method was developed that allows for relative comparison of the... (More)

β-Mannanases catalyze the conversion and modification of β-mannans and may, in addition to hydrolysis, also be capable of transglycosylation which can result in enzymatic synthesis of novel glycoconjugates. Using alcohols as glycosyl acceptors (alcoholysis), β-mannanases can potentially be used to synthesize alkyl glycosides, biodegradable surfactants, from renewable β-mannans. In this paper, we investigate the synthesis of alkyl mannooligosides using glycoside hydrolase family 5 β-mannanases from the fungi Trichoderma reesei (TrMan5A and TrMan5A-R171K) and Aspergillus nidulans (AnMan5C). To evaluate β-mannanase alcoholysis capacity, a novel mass spectrometry-based method was developed that allows for relative comparison of the formation of alcoholysis products using different enzymes or reaction conditions. Differences in alcoholysis capacity and potential secondary hydrolysis of alkyl mannooligosides were observed when comparing alcoholysis catalyzed by the three β-mannanases using methanol or 1-hexanol as acceptor. Among the three β-mannanases studied, TrMan5A was the most efficient in producing hexyl mannooligosides with 1-hexanol as acceptor. Hexyl mannooligosides were synthesized using TrMan5A and purified using high-performance liquid chromatography. The data suggests a high selectivity of TrMan5A for 1-hexanol as acceptor over water. The synthesized hexyl mannooligosides were structurally characterized using nuclear magnetic resonance, with results in agreement with their predicted β-conformation. The surfactant properties of the synthesized hexyl mannooligosides were evaluated using tensiometry, showing that they have similar micelle-forming properties as commercially available hexyl glucosides. The present paper demonstrates the possibility of using β-mannanases for alkyl glycoside synthesis and increases the potential utilization of renewable β-mannans.

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published
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keywords
Alcoholysis, Alkyl glycoside, Surfactant, Transglycosylation, β-Mannanase
in
Applied Microbiology and Biotechnology
volume
102
issue
12
pages
15 pages
publisher
Springer
external identifiers
  • scopus:85045744814
ISSN
0175-7598
DOI
10.1007/s00253-018-8997-2
language
English
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yes
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5dcdf96d-fd01-488e-82e6-e969ea2b4913
date added to LUP
2018-05-23 08:39:35
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2019-10-15 06:38:30
@article{5dcdf96d-fd01-488e-82e6-e969ea2b4913,
  abstract     = {<p>β-Mannanases catalyze the conversion and modification of β-mannans and may, in addition to hydrolysis, also be capable of transglycosylation which can result in enzymatic synthesis of novel glycoconjugates. Using alcohols as glycosyl acceptors (alcoholysis), β-mannanases can potentially be used to synthesize alkyl glycosides, biodegradable surfactants, from renewable β-mannans. In this paper, we investigate the synthesis of alkyl mannooligosides using glycoside hydrolase family 5 β-mannanases from the fungi Trichoderma reesei (TrMan5A and TrMan5A-R171K) and Aspergillus nidulans (AnMan5C). To evaluate β-mannanase alcoholysis capacity, a novel mass spectrometry-based method was developed that allows for relative comparison of the formation of alcoholysis products using different enzymes or reaction conditions. Differences in alcoholysis capacity and potential secondary hydrolysis of alkyl mannooligosides were observed when comparing alcoholysis catalyzed by the three β-mannanases using methanol or 1-hexanol as acceptor. Among the three β-mannanases studied, TrMan5A was the most efficient in producing hexyl mannooligosides with 1-hexanol as acceptor. Hexyl mannooligosides were synthesized using TrMan5A and purified using high-performance liquid chromatography. The data suggests a high selectivity of TrMan5A for 1-hexanol as acceptor over water. The synthesized hexyl mannooligosides were structurally characterized using nuclear magnetic resonance, with results in agreement with their predicted β-conformation. The surfactant properties of the synthesized hexyl mannooligosides were evaluated using tensiometry, showing that they have similar micelle-forming properties as commercially available hexyl glucosides. The present paper demonstrates the possibility of using β-mannanases for alkyl glycoside synthesis and increases the potential utilization of renewable β-mannans.</p>},
  author       = {Morrill, Johan and Månberger, Anna and Rosengren, Anna and Naidjonoka, Polina and von Freiesleben, Pernille and Krogh, Kristian B.R.M. and Bergquist, Karl Erik and Nylander, Tommy and Karlsson, Eva Nordberg and Adlercreutz, Patrick and Stålbrand, Henrik},
  issn         = {0175-7598},
  keyword      = {Alcoholysis,Alkyl glycoside,Surfactant,Transglycosylation,β-Mannanase},
  language     = {eng},
  month        = {04},
  number       = {12},
  pages        = {5149--5163},
  publisher    = {Springer},
  series       = {Applied Microbiology and Biotechnology},
  title        = {β-Mannanase-catalyzed synthesis of alkyl mannooligosides},
  url          = {http://dx.doi.org/10.1007/s00253-018-8997-2},
  volume       = {102},
  year         = {2018},
}