| Title | Leuconostoc mesenteroides glucansucrase synthesis of flavonoid glucosides by acceptor reactions in aqueous-organic solvents |
|---|---|
| Author | Anne Bertrand, Sandrine Morel, François Lefoulon, Yves Rolland, Pierre Monsan, Magali Remaud-Simeon |
| DOI | 10.1016/j.carres.2006.02.008 |
| Abstract | The enzymatic glucosylation of luteolin was attempted using two glucansucrases: the dextransucrase from Leuconostoc mesenteroides NRRL B-512F and the alternansucrase from L. mesenteroides NRRL B-23192. Reactions were carried out in aqueous-organic solvents to improve luteolin solubility. A molar conversion of 44% was achieved after 24h of reaction catalysed by dextransucrase from L. mesenteroides NRRL B-512F in a mixture of acetate buffer (70%)/bis(2-methoxyethyl) ether (30%). Two products were characterised by nuclear magnetic resonance (NMR) spectroscopy: luteolin-3’-O-alpha-d-glucopyranoside and luteolin-4’-O-alpha-d-glucopyranoside. In the presence of alternansucrase from L. mesenteroides NRRL B-23192, three additional products were obtained with a luteolin conversion of 8%. Both enzymes were also able to glucosylate quercetin and myricetin with conversion of 4% and 49%, respectively. |
Uniprot ID: Q9RE05
Protein: Dextransucrase
Organism: Leuconostoc mesenteroides
Length: 2,057 AA
Taxonomic identifier: 1245 [NCBI]
| Source | Domain | Start | End | E-value (Domain) | Coverage |
|---|---|---|---|---|---|
| Pfam-A | Glyco_hydro_70 | 453 | 1312 | 4.8e-302 | 0.998 |
Program: hmmscan
Version: 3.1b2 (February 2015)
Method: hmmscan --domtblout hmmscan.tbl --noali -E 1e-5 pfam query.fa
Date: Mon Jul 20 14:32:16 2020
Description:
Glyco_hydro_70
Members of this family belong to glycosyl hydrolase family 70[1] Glucosyltransferases or sucrose 6-glycosyl transferases (GTF-S) catalyse the transfer of D-glucopyramnosyl units from sucrose onto acceptor molecules[2] EC:2.4.1.5. This family roughly corresponds to the N-terminal catalytic domain of the enzyme. Members of this family also contain the Putative cell wall binding domain PF01473 which corresponds with the C-terminal glucan-binding domain.
O-Glycosyl hydrolases (3.2.1.) are a widespread group of enzymes that hydrolyse the glycosidic bond between two or more carbohydrates, or between a carbohydrate and a non-carbohydrate moiety. A classification system for glycosyl hydrolases, based on sequence similarity, has led to the definition of 85 different families [3][4]. This classification is available on the CAZy (CArbohydrate-Active EnZymes) website.
Glucosyltransferases or sucrose 6-glycosyl transferases (GTF-S) (2.4.1.5, GH70) catalyse the transfer of D-glucopyramnosyl units from sucrose onto acceptor molecules [2:1]. This entry represents a domain that roughly corresponds to the N-terminal catalytic domain of the enzyme. Members of this family also contain the putative cell wall binding domain PF01473 which corresponds with the C-terminal glucan-binding domain.
Information is taken from Pfam and InterPro web site.
luteolin ⇒ luteolin-3’-O-α-D-glucopyranoside + luteolin-4’-O-α-Dglucopyranoside + luteolin-4’-O-α-D-tri-glucoside + luteolin-4’-O-α-di-glucosides
Henrissat B. A classification of glycosyl hydrolases based on amino acid sequence similarities[J]. Biochemical journal, 1991, 280(2): 309-316. ↩︎
Monchois V, Willemot R M, Remaud-Simeon M, et al. Cloning and sequencing of a gene coding for a novel dextransucrase from Leuconostoc mesenteroides NRRL B-1299 synthesizing only α (1–6) and α (1–3) linkages[J]. Gene, 1996, 182(1-2): 23-32. ↩︎ ↩︎
Henrissat B, Callebaut I, Fabrega S, et al. Conserved catalytic machinery and the prediction of a common fold for several families of glycosyl hydrolases[J]. Proceedings of the National Academy of Sciences, 1995, 92(15): 7090-7094. ↩︎
Davies G, Henrissat B. Structures and mechanisms of glycosyl hydrolases[J]. Structure, 1995, 3(9): 853-859. ↩︎
| Title | Leuconostoc mesenteroides glucansucrase synthesis of flavonoid glucosides by acceptor reactions in aqueous-organic solvents |
|---|---|
| Author | Anne Bertrand, Sandrine Morel, François Lefoulon, Yves Rolland, Pierre Monsan, Magali Remaud-Simeon |
| DOI | 10.1016/j.carres.2006.02.008 |
| Abstract | The enzymatic glucosylation of luteolin was attempted using two glucansucrases: the dextransucrase from Leuconostoc mesenteroides NRRL B-512F and the alternansucrase from L. mesenteroides NRRL B-23192. Reactions were carried out in aqueous-organic solvents to improve luteolin solubility. A molar conversion of 44% was achieved after 24h of reaction catalysed by dextransucrase from L. mesenteroides NRRL B-512F in a mixture of acetate buffer (70%)/bis(2-methoxyethyl) ether (30%). Two products were characterised by nuclear magnetic resonance (NMR) spectroscopy: luteolin-3’-O-alpha-d-glucopyranoside and luteolin-4’-O-alpha-d-glucopyranoside. In the presence of alternansucrase from L. mesenteroides NRRL B-23192, three additional products were obtained with a luteolin conversion of 8%. Both enzymes were also able to glucosylate quercetin and myricetin with conversion of 4% and 49%, respectively. |
Uniprot ID: Q9ZAR4
Protein: Dextransucrase
Organism: Leuconostoc mesenteroides
Length: 1,527 AA
Taxonomic identifier: 1245 [NCBI]
| Source | Domain | Start | End | E-value (Domain) | Coverage |
|---|---|---|---|---|---|
| Pfam-A | Glyco_hydro_70 | 370 | 1169 | 0 | 0.999 |
Program: hmmscan
Version: 3.1b2 (February 2015)
Method: hmmscan --domtblout hmmscan.tbl --noali -E 1e-5 pfam query.fa
Date: Mon Jul 20 14:32:16 2020
Description:
Glyco_hydro_70
Members of this family belong to glycosyl hydrolase family 70[1] Glucosyltransferases or sucrose 6-glycosyl transferases (GTF-S) catalyse the transfer of D-glucopyramnosyl units from sucrose onto acceptor molecules[2] EC:2.4.1.5. This family roughly corresponds to the N-terminal catalytic domain of the enzyme. Members of this family also contain the Putative cell wall binding domain PF01473 which corresponds with the C-terminal glucan-binding domain.
O-Glycosyl hydrolases (3.2.1.) are a widespread group of enzymes that hydrolyse the glycosidic bond between two or more carbohydrates, or between a carbohydrate and a non-carbohydrate moiety. A classification system for glycosyl hydrolases, based on sequence similarity, has led to the definition of 85 different families [3][4]. This classification is available on the CAZy (CArbohydrate-Active EnZymes) website.
Glucosyltransferases or sucrose 6-glycosyl transferases (GTF-S) (2.4.1.5, GH70) catalyse the transfer of D-glucopyramnosyl units from sucrose onto acceptor molecules [2:1]. This entry represents a domain that roughly corresponds to the N-terminal catalytic domain of the enzyme. Members of this family also contain the putative cell wall binding domain PF01473 which corresponds with the C-terminal glucan-binding domain.
Information is taken from Pfam and InterPro web site.
luteolin ⇒ luteolin-3’-O-α-D-glucopyranoside + luteolin-4’-O-α-Dglucopyranoside
![[L1]luteolin](../static/images/chemical_structure/FR2/[L1]luteolin.png)
![[R1]luteolin-3'-O-a-D-glucopyranoside](../static/images/chemical_structure/FR2/[R1]luteolin-3'-O-a-D-glucopyranoside.png)
![[R2]luteolin-4'-O-a-D-glucopyranoside](../static/images/chemical_structure/FR2/[R2]luteolin-4'-O-a-D-glucopyranoside.png)
Henrissat B. A classification of glycosyl hydrolases based on amino acid sequence similarities[J]. Biochemical journal, 1991, 280(2): 309-316. ↩︎
Monchois V, Willemot R M, Remaud-Simeon M, et al. Cloning and sequencing of a gene coding for a novel dextransucrase from Leuconostoc mesenteroides NRRL B-1299 synthesizing only α (1–6) and α (1–3) linkages[J]. Gene, 1996, 182(1-2): 23-32. ↩︎ ↩︎
Henrissat B, Callebaut I, Fabrega S, et al. Conserved catalytic machinery and the prediction of a common fold for several families of glycosyl hydrolases[J]. Proceedings of the National Academy of Sciences, 1995, 92(15): 7090-7094. ↩︎
Davies G, Henrissat B. Structures and mechanisms of glycosyl hydrolases[J]. Structure, 1995, 3(9): 853-859. ↩︎