Chemoenzymatic synthesis of sialylated lactuloses and their inhibitory effects on Staphylococcus aureus.
BACKGROUND:Sialylated glycoconjugates play important roles in physiological and pathological processes. However, available sialylated oligosaccharides source is limited which is a barrier to study their biological roles. This work reports an efficient approach to produce sialic acid-modified lactulo...
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| Format: | Article |
| Language: | English |
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Public Library of Science (PLoS)
2018-01-01
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| Series: | PLoS ONE |
| Online Access: | http://europepmc.org/articles/PMC6010273?pdf=render |
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| author | Jie Zeng Yajie Hu Tian Jia Ruiyao Zhang Tongchao Su Junliang Sun Haiyan Gao Guanglei Li Meng Cao Mengdi Song |
| author_facet | Jie Zeng Yajie Hu Tian Jia Ruiyao Zhang Tongchao Su Junliang Sun Haiyan Gao Guanglei Li Meng Cao Mengdi Song |
| author_sort | Jie Zeng |
| collection | DOAJ |
| description | BACKGROUND:Sialylated glycoconjugates play important roles in physiological and pathological processes. However, available sialylated oligosaccharides source is limited which is a barrier to study their biological roles. This work reports an efficient approach to produce sialic acid-modified lactuloses and investigates their inhibitory effects on Staphylococcus aureus (S. aureus). METHODS:A one-pot two-enzyme (OPTE) sialylation system was used to efficiently synthesize sialylated lactuloses. Silica gel flash chromatography column was employed to purify the sialylated products. The purity and identity of the product structures were confirmed with mass spectrometry (MS) and nuclear magnetic resonance (NMR). The inhibitory effect of sialylated lactuloses against S. aureus was evaluated by using microplate assay, fluorescence microscopy, DAPI (4',6-diamidino-2-phenylindole) fluorescence staining and protein leakage quantification. RESULTS:Neu5Ac-containing sialylated lactuloses with either α2,3- or α2,6-linkages were efficiently synthesized via an efficient OPTE sialylation system using α-2,3-sialyltransferase or α-2,6-sialyltransferase, respectively. Neu5Ac-α2,3-lactulose and Neu5Ac-α2,6-lactulose significantly inhibited the growth of S. aureus. Fluorescence microscopy and DAPI fluorescence staining indicated that the sialylated lactuloses might disrupt nucleic acid synthesis of S. aureus. CONCLUSIONS:Neu5Ac-containing sialylated lactuloses had higher antibacterial activity against S. aureus than non-sialylated lactulose. The inhibitory effect of Neu5Ac-α2,3-lactulose was superior to that of Neu5Ac-α2,6-lactulose. The sialylated lactuloses might inhibit S. aureus by causing cell membrane leakage and disrupting nucleic acid synthesis. |
| first_indexed | 2024-04-12T12:42:15Z |
| format | Article |
| id | doaj.art-f2589864f20a49ef952fd44b79b7e299 |
| institution | Directory Open Access Journal |
| issn | 1932-6203 |
| language | English |
| last_indexed | 2024-04-12T12:42:15Z |
| publishDate | 2018-01-01 |
| publisher | Public Library of Science (PLoS) |
| record_format | Article |
| series | PLoS ONE |
| spelling | doaj.art-f2589864f20a49ef952fd44b79b7e2992022-12-22T03:32:45ZengPublic Library of Science (PLoS)PLoS ONE1932-62032018-01-01136e019933410.1371/journal.pone.0199334Chemoenzymatic synthesis of sialylated lactuloses and their inhibitory effects on Staphylococcus aureus.Jie ZengYajie HuTian JiaRuiyao ZhangTongchao SuJunliang SunHaiyan GaoGuanglei LiMeng CaoMengdi SongBACKGROUND:Sialylated glycoconjugates play important roles in physiological and pathological processes. However, available sialylated oligosaccharides source is limited which is a barrier to study their biological roles. This work reports an efficient approach to produce sialic acid-modified lactuloses and investigates their inhibitory effects on Staphylococcus aureus (S. aureus). METHODS:A one-pot two-enzyme (OPTE) sialylation system was used to efficiently synthesize sialylated lactuloses. Silica gel flash chromatography column was employed to purify the sialylated products. The purity and identity of the product structures were confirmed with mass spectrometry (MS) and nuclear magnetic resonance (NMR). The inhibitory effect of sialylated lactuloses against S. aureus was evaluated by using microplate assay, fluorescence microscopy, DAPI (4',6-diamidino-2-phenylindole) fluorescence staining and protein leakage quantification. RESULTS:Neu5Ac-containing sialylated lactuloses with either α2,3- or α2,6-linkages were efficiently synthesized via an efficient OPTE sialylation system using α-2,3-sialyltransferase or α-2,6-sialyltransferase, respectively. Neu5Ac-α2,3-lactulose and Neu5Ac-α2,6-lactulose significantly inhibited the growth of S. aureus. Fluorescence microscopy and DAPI fluorescence staining indicated that the sialylated lactuloses might disrupt nucleic acid synthesis of S. aureus. CONCLUSIONS:Neu5Ac-containing sialylated lactuloses had higher antibacterial activity against S. aureus than non-sialylated lactulose. The inhibitory effect of Neu5Ac-α2,3-lactulose was superior to that of Neu5Ac-α2,6-lactulose. The sialylated lactuloses might inhibit S. aureus by causing cell membrane leakage and disrupting nucleic acid synthesis.http://europepmc.org/articles/PMC6010273?pdf=render |
| spellingShingle | Jie Zeng Yajie Hu Tian Jia Ruiyao Zhang Tongchao Su Junliang Sun Haiyan Gao Guanglei Li Meng Cao Mengdi Song Chemoenzymatic synthesis of sialylated lactuloses and their inhibitory effects on Staphylococcus aureus. PLoS ONE |
| title | Chemoenzymatic synthesis of sialylated lactuloses and their inhibitory effects on Staphylococcus aureus. |
| title_full | Chemoenzymatic synthesis of sialylated lactuloses and their inhibitory effects on Staphylococcus aureus. |
| title_fullStr | Chemoenzymatic synthesis of sialylated lactuloses and their inhibitory effects on Staphylococcus aureus. |
| title_full_unstemmed | Chemoenzymatic synthesis of sialylated lactuloses and their inhibitory effects on Staphylococcus aureus. |
| title_short | Chemoenzymatic synthesis of sialylated lactuloses and their inhibitory effects on Staphylococcus aureus. |
| title_sort | chemoenzymatic synthesis of sialylated lactuloses and their inhibitory effects on staphylococcus aureus |
| url | http://europepmc.org/articles/PMC6010273?pdf=render |
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