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Chemoenzymatic approach toward the synthesis of 3-O-(α/β)-glucosylated 3-hydroxy-β-lactams

(2018) ACS OMEGA. 3(11). p.15235-15245
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Abstract
Glycosylation significantly alters the biological and physicochemical properties of small molecules. beta-Lactam alcohols comprise eligible substrates for such a transformation based on their distinct relevance in the chemical and medicinal community. In this framework, the unprecedented enzymatic glycosylation of the rigid and highly strained four-membered beta-lactam azaheterocycle was studied. For this purpose, cis-3-hydroxy-beta-lactams were efficiently prepared in three steps by means of a classical organic synthesis approach, while a biocatalytic step was implemented for the selective formation of the corresponding 3-O-alpha- and -beta-glucosides, hence overcoming the complexities typically encountered in synthetic glycochemistry and contributing to the increasing demand for sustainable processes in the framework of green chemistry. Two carbohydrate-active enzymes were selected based on their broad acceptor specificity and subsequently applied for the alpha- or beta-selective formation of beta-lactam-sugar adducts, using sucrose as a glucosyl donor.
Keywords
BETA-LACTAM, ASYMMETRIC-SYNTHESIS, ENZYMATIC GLYCOSYLATION, SUCROSE PHOSPHORYLASE, SIDE-CHAIN, INHIBITORS, EFFICIENT, GLYCOSYLTRANSFERASES, DISACCHARIDE, ANTIBIOTICS

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Citation

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Chicago
Decuyper, Lena, Jorick Franceus, Shari Dhaene, Maarten Debruyne, Kevin Vandoorne, Nicola Piens, Griet Dewitte, Tom Desmet, and Matthias D’hooghe. 2018. “Chemoenzymatic Approach Toward the Synthesis of 3-O-(α/β)-glucosylated 3-hydroxy-β-lactams.” Acs Omega 3 (11): 15235–15245.
APA
Decuyper, L., Franceus, J., Dhaene, S., Debruyne, M., Vandoorne, K., Piens, N., Dewitte, G., et al. (2018). Chemoenzymatic approach toward the synthesis of 3-O-(α/β)-glucosylated 3-hydroxy-β-lactams. ACS OMEGA, 3(11), 15235–15245.
Vancouver
1.
Decuyper L, Franceus J, Dhaene S, Debruyne M, Vandoorne K, Piens N, et al. Chemoenzymatic approach toward the synthesis of 3-O-(α/β)-glucosylated 3-hydroxy-β-lactams. ACS OMEGA. 2018;3(11):15235–45.
MLA
Decuyper, Lena et al. “Chemoenzymatic Approach Toward the Synthesis of 3-O-(α/β)-glucosylated 3-hydroxy-β-lactams.” ACS OMEGA 3.11 (2018): 15235–15245. Print.
@article{8598662,
  abstract     = {Glycosylation significantly alters the biological and physicochemical properties of small molecules. beta-Lactam alcohols comprise eligible substrates for such a transformation based on their distinct relevance in the chemical and medicinal community. In this framework, the unprecedented enzymatic glycosylation of the rigid and highly strained four-membered beta-lactam azaheterocycle was studied. For this purpose, cis-3-hydroxy-beta-lactams were efficiently prepared in three steps by means of a classical organic synthesis approach, while a biocatalytic step was implemented for the selective formation of the corresponding 3-O-alpha- and -beta-glucosides, hence overcoming the complexities typically encountered in synthetic glycochemistry and contributing to the increasing demand for sustainable processes in the framework of green chemistry. Two carbohydrate-active enzymes were selected based on their broad acceptor specificity and subsequently applied for the alpha- or beta-selective formation of beta-lactam-sugar adducts, using sucrose as a glucosyl donor.},
  author       = {Decuyper, Lena and Franceus, Jorick and Dhaene, Shari and Debruyne, Maarten and Vandoorne, Kevin and Piens, Nicola and Dewitte, Griet and Desmet, Tom and D'hooghe, Matthias},
  issn         = {2470-1343},
  journal      = {ACS OMEGA},
  language     = {eng},
  number       = {11},
  pages        = {15235--15245},
  title        = {Chemoenzymatic approach toward the synthesis of 3-O-(\ensuremath{\alpha}/\ensuremath{\beta})-glucosylated 3-hydroxy-\ensuremath{\beta}-lactams},
  url          = {http://dx.doi.org/10.1021/acsomega.8b01969},
  volume       = {3},
  year         = {2018},
}

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