2.4.1.140: alternansucrase
This is an abbreviated version!
For detailed information about alternansucrase, go to the full flat file.
Word Map on EC 2.4.1.140
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2.4.1.140
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leuconostoc
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mesenteroides
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lactobacillus
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dextrans
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glucosylated
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dextransucrase
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prebiotic
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citreum
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gluco-oligosaccharides
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reuteransucrase
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reuteran
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glucosyltransferases
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weissella
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confusa
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levansucrase
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cibaria
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alpha-d-glucans
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glucan-binding
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downei
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homopolysaccharide
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fructansucrase
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transglucosylation
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alpha-1,6
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synthesis
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drug development
- 2.4.1.140
- leuconostoc
- mesenteroides
- lactobacillus
- dextrans
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glucosylated
- dextransucrase
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prebiotic
- citreum
- gluco-oligosaccharides
-
reuteransucrase
-
reuteran
-
glucosyltransferases
- weissella
- confusa
- levansucrase
- cibaria
- alpha-d-glucans
-
glucan-binding
- downei
-
homopolysaccharide
- fructansucrase
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transglucosylation
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alpha-1,6
- synthesis
- drug development
Reaction
Synonyms
alternansucrase, ASR, glucansucrase, glucosyltransferase, sucrose-1,6(3)-alpha-glucan 6(3)-alpha-, Lcalt, sucrose:1,6-, 1,3-alpha-D-glucan 3-alpha- and 6-alpha-D-glucosyltransferase
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2.4.1.140 alternansucraseAdvanced search results
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results (Substrates Products
Substrates Products on EC 2.4.1.140 - alternansucrase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
sucrose + leucrose
?
-
regioselectivity of alternansucrase differs from dextransucrase. Alternansucrase shows greater ability to use leucrose as an acceptor, alternansucrase continues to transfer glucosyl units to leucrose, resulting in some unusual glucosyl-fructose oligosaccharides
-
-
?
sucrose + luteolin
luteolin-3'-O-alpha-D-glucopyranoside + luteolin-4'-O-alpha-D-glucopyranoside
sucrose + methyl alpha-D-allo-pyranoside
methyl alpha-D-glucopyranosyl-(1,6)-alpha-D-allopyranoside + alpha-D-glucopyranosyl-(1,6)-alpha-D-glucopyranosyl-(1,6)-alpha-D-allopyranoside + beta-D-fructofuranose
-
-
the product methyl alpha-D-glucopyranosyl-(1,6)-alpha-D-allopyranoside is subsequently glucosylated at position 6 to give rise to the trisaccharide methyl alpha-D-glucopyranosyl-(1,6)-alpha-D-glucopyranosyl-(1,6)-alpha-D-allopyranoside. Higher DP products are observed
-
?
sucrose + methyl alpha-D-galactopyranoside
methyl alpha-D-glucopyranosyl-(1,3)-alpha-D-galactopyranoside + methyl alpha-D-glucopyranosyl-(1,4)-alpha-D-galactopyranoside + beta-D-fructofuranose
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two initial products methyl alpha-D-glucopyranosyl-(1,3)-alpha-D-galactopyranoside and methyl alpha-D-glucopyranosyl-(1,4)-alpha-D-galactopyranoside, in a 2.5:1 molar ratio
-
?
sucrose + methyl alpha-D-galactopyranoside
methyl alpha-D-glucopyranosyl-(1,4)-alpha-D-galactopyranoside + methyl alpha-D-glucopyranosyl-(1,3)-alpha-D-galactopyranoside + beta-D-fructofuranose
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-
production of methyl alpha-D-glucopyranosyl-(1, 4)-alpha-D-galactopyranoside and methyl alpha-D-glucopyranosyl-(1,3)-alpha-D-galactopyranoside in the ratio 2.5:1
-
?
sucrose + methyl alpha-D-mannopyranoside
methyl alpha-D-glucopyranosyl-(1,6)-alpha-D-mannopyranoside + methyl-3,6-di-O-alpha-D-glucopyranosyl-alpha-D-mannopyranoside + beta-D-fructofuranose
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-
the major initial acceptor product is methyl alpha-D-glucopyranosyl-(1,6)-alpha-D-mannopyranoside, but several minor products are also isolated and characterized, including a 3,6-di-O-substituted mannopyranoside
-
?
sucrose + methyl-beta-D-glucopyranoside
methyl beta-isomaltoside + methyl beta-isomaltotrioside + methyl alpha-D-glucopyranosyl-(1,3)-alpha-D-glucopyranosyl-(1,6)-beta-D-glucopyranoside + beta-D-fructofuranose
-
-
the initial product arising is methyl beta-isomaltoside, which is subsequently glucosylated to yield methyl beta-isomaltotrioside and methyl alpha-D-glucopyranosyl-(1,3)-alpha-D-glucopyranosyl-(1,6)-beta-D-glucopyranoside
-
?
stevioside + sucrose
?
-
transglucosylation
the product is composed of mono-, di-, and triglucosylated stevioside and their isomers
-
?
stevioside + sucrose
?
-
transglucosylation
the product is composed of mono-, di-, and triglucosylated stevioside and their isomers
-
?
sucrose + alpha-D-glucan
alternating-1,6-1,3-alpha-D-glucan
-
-
-
?
sucrose + alpha-D-glucan
alternating-1,6-1,3-alpha-D-glucan
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-
-
?
sucrose + alpha-D-glucan
alternating-1,6-1,3-alpha-D-glucan
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-
-
-
?
sucrose + alpha-D-glucan
alternating-1,6-1,3-alpha-D-glucan
-
-
-
?
sucrose + alpha-D-glucan
alternating-1,6-1,3-alpha-D-glucan
-
-
-
?
sucrose + alpha-D-glucan
alternating-1,6-1,3-alpha-D-glucan
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-
-
-
?
sucrose + alpha-D-glucan
alternating-1,6-1,3-alpha-D-glucan
-
-
-
-
?
sucrose + alpha-D-glucan
alternating-1,6-1,3-alpha-D-glucan
-
-
-
-
?
sucrose + alpha-D-glucan
alternating-1,6-1,3-alpha-D-glucan
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-
the product is an insoluble D-glucan that consists of 76 mol% 1,3-alpha-linked glucose and 24 mol% 1,6-alpha-linked glucose
?
sucrose + alpha-D-glucan
alternating-1,6-1,3-alpha-D-glucan
-
-
glucan consists of 49.1 mol% 1,6-alpha-linked glucose and 33.9 mol% 1,3-alpha-linked glucose with 13.6 mol% terminal glucose and 3.3 mol% 1,3,6-alpha-branched glucose
?
sucrose + alpha-D-glucopyranosyl-(1,4)-L-glucose
?
-
-
-
-
?
sucrose + cellobiose
oligosaccharides
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-
alpha-D-glucopyranosyl-(1,2)-(beta-D-glucopyranosyl-(1,4))-D-glucopyranose + alpha-D-glucopyranosyl-(1,6)-beta-D-glucopyranosyl-(1,4)-D-glucopyranose, the last compound in turn can be glycosylated leading to the synthesis of a tetrasaccharide with an additional alpha-(1,6)-linkage at the non-reducing end
?
sucrose + cellobiose
oligosaccharides
-
-
alpha-D-glucopyranosyl-(1,2)-(beta-D-glucopyranosyl-(1,4))-D-glucopyranose + alpha-D-glucopyranosyl-(1,6)-beta-D-glucopyranosyl-(1,4)-D-glucopyranose, the last compound in turn can be glycosylated leading to the synthesis of a tetrasaccharide with an additional alpha-(1,6)-linkage at the non-reducing end
?
sucrose + D-tagatose
alpha-D-glucopyranosyl-(1,1)-beta-D-tagatopyranose
-
-
-
-
?
sucrose + D-tagatose
alpha-D-glucopyranosyl-(1,1)-beta-D-tagatopyranose
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-
-
-
?
sucrose + gentiobiose
?
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gentiobiose is better as an acceptor than isomaltose, acceptor products from gentiobiose, form in good yields (nearly 90% in unoptimized reactions). The initial product is a single trisaccharide, alpha-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-D-Glc. Two tetrasaccharides are formed in approximately equal quantities: alpha-D-Glcp-(1-3)-alpha-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-D-Glc and alpha-D-Glcp-(1-6)-alpha-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-D-Glc. One pentasaccharide is isolated from the reaction mixture, alpha-D-Glcp-(1-6)-alpha-D-Glcp-(1-3)-alpha-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-D-Glc
-
-
?
sucrose + gentiobiose
?
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gentiobiose is better as an acceptor than isomaltose, acceptor products from gentiobiose, form in good yields (nearly 90% in unoptimized reactions). The initial product is a single trisaccharide, alpha-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-D-Glc. Two tetrasaccharides are formed in approximately equal quantities: alpha-D-Glcp-(1-3)-alpha-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-D-Glc and alpha-D-Glcp-(1-6)-alpha-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-D-Glc. One pentasaccharide is isolated from the reaction mixture, alpha-D-Glcp-(1-6)-alpha-D-Glcp-(1-3)-alpha-D-Glcp-(1-6)-beta-D-Glcp-(1-6)-D-Glc
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-
?
sucrose + L-glucose
alpha-D-glucopyranosyl-(1,6)-alpha-D-glucopyranosyl-(1,4)-L-glucose
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-
-
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?
sucrose + L-glucose
alpha-D-glucopyranosyl-(1,6)-alpha-D-glucopyranosyl-(1,4)-L-glucose
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-
-
-
?
sucrose + luteolin
luteolin-3'-O-alpha-D-glucopyranoside + luteolin-4'-O-alpha-D-glucopyranoside
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8% conversion
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-
?
sucrose + luteolin
luteolin-3'-O-alpha-D-glucopyranoside + luteolin-4'-O-alpha-D-glucopyranoside
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8% conversion
-
-
?
sucrose + luteolin
luteolin-3'-O-alpha-D-glucopyranoside + luteolin-4'-O-alpha-D-glucopyranoside
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8% conversion
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-
?
sucrose + maltose
?
maltose undergoes alpha-1,6 glucosylation alone to give the oligodextran of DP3 (OD3 panose, alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->4)-D-Glc), which can be further elongated at either the O6 or the O3 position of the nonreducing unit to give the structures OD4 (alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->4)-D-Glc) and OA4 (alpha-D-Glcp-(1->3)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->4)-D-Glc), respectively. The oligosaccharide OA4 is quick to appear at the beginning of the reaction (1 min) and accumulates at a much higher level than OD4, indicating that panose is preferentially elongated with an alpha-1,3 linkage. A very small peak of OD5 originating from OD4 only appears toward the end of the reaction (after about 30 min) and is not elongated further (no OD6 is found). As soon as the OA4 starts to accumulate, it is efficiently converts to OA5 (alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->3)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->4)-D-Glc). The OA5 itself can act as an acceptor for the formation of two OA6s (alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->3)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->4)-DGlc and alpha-D-Glcp-(1->3)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->3)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->4)-D-Glc)
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-
?
sucrose + maltose
?
Leuconostoc citreum NRRL B-1355
maltose undergoes alpha-1,6 glucosylation alone to give the oligodextran of DP3 (OD3 panose, alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->4)-D-Glc), which can be further elongated at either the O6 or the O3 position of the nonreducing unit to give the structures OD4 (alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->4)-D-Glc) and OA4 (alpha-D-Glcp-(1->3)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->4)-D-Glc), respectively. The oligosaccharide OA4 is quick to appear at the beginning of the reaction (1 min) and accumulates at a much higher level than OD4, indicating that panose is preferentially elongated with an alpha-1,3 linkage. A very small peak of OD5 originating from OD4 only appears toward the end of the reaction (after about 30 min) and is not elongated further (no OD6 is found). As soon as the OA4 starts to accumulate, it is efficiently converts to OA5 (alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->3)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->4)-D-Glc). The OA5 itself can act as an acceptor for the formation of two OA6s (alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->3)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->4)-DGlc and alpha-D-Glcp-(1->3)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->3)-alpha-D-Glcp-(1->6)-alpha-D-Glcp-(1->4)-D-Glc)
-
-
?
sucrose + maltose
?
-
alternansucrase acceptor products from maltose do not contain dextran-type linkage sequences. Instead, the product series is comprised of an alternan-type linkage sequence, with some pairs of consecutive alpha-(1,6) linkages in the evennumbered members of the series. The distribution and sequence of linkages is apparently kinetically controlled. Branch formation is not detected below DP 8. Alternansucrase forms alpha-(1,3) linkages only when the acceptor is a-(1,6)-linked, thereby prohibiting the formation of sequences of alpha-(1,3) linkages. Furthermore, the enzyme appears not to make products containing more than two sequential alpha-(1,6) linkages, thereby prohibiting the formation of dextran-like linkage sequences
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-
?
sucrose + maltose
?
-
alternansucrase acceptor products from maltose do not contain dextran-type linkage sequences. Instead, the product series is comprised of an alternan-type linkage sequence, with some pairs of consecutive alpha-(1,6) linkages in the evennumbered members of the series. The distribution and sequence of linkages is apparently kinetically controlled. Branch formation is not detected below DP 8. Alternansucrase forms alpha-(1,3) linkages only when the acceptor is a-(1,6)-linked, thereby prohibiting the formation of sequences of alpha-(1,3) linkages. Furthermore, the enzyme appears not to make products containing more than two sequential alpha-(1,6) linkages, thereby prohibiting the formation of dextran-like linkage sequences
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-
?
sucrose + maltose
oligoalternan
-
-
panose is the first acceptor product
?
sucrose + maltose
oligoalternan
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-
panose is the first acceptor product
?
sucrose + methyl-alpha-D-glucoside
oligoalternan
-
-
-
?
sucrose + raffinose
?
-
the alternansucrase-catalyzed acceptor reaction with raffinose gives a gravimetric yield of alternan of 9.5% relative to the weight of sucrose, indicating that 20% of the glucosyl units are incorporated into alternan, and 80% into oligosaccharide acceptor products. The main products are the tetrasaccharides alpha-D-Glcp-(1-3)-alpha-D-Galp-(1-6)-alpha-D-Glcp-(1-2)-beta-D-Fruf and alpha-D-Glcp-(1-4)-alpha-D-Galp-(1-6)-alpha-D-Glcp-(1-2)-beta-D-Fruf in ratios ranging from 4:1 to 9:1, along with lesser amounts of alpha-D-Glcp-(1-6)-alpha-D-Galp-(1-6)-alpha-D-Glcp-(1-2)-beta-D-Fruf. Pentasaccharides, hexasaccharides and higher oligosaccharides are also produced
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-
?
sucrose + raffinose
?
-
the alternansucrase-catalyzed acceptor reaction with raffinose gives a gravimetric yield of alternan of 9.5% relative to the weight of sucrose, indicating that 20% of the glucosyl units are incorporated into alternan, and 80% into oligosaccharide acceptor products. The main products are the tetrasaccharides alpha-D-Glcp-(1-3)-alpha-D-Galp-(1-6)-alpha-D-Glcp-(1-2)-beta-D-Fruf and alpha-D-Glcp-(1-4)-alpha-D-Galp-(1-6)-alpha-D-Glcp-(1-2)-beta-D-Fruf in ratios ranging from 4:1 to 9:1, along with lesser amounts of alpha-D-Glcp-(1-6)-alpha-D-Galp-(1-6)-alpha-D-Glcp-(1-2)-beta-D-Fruf. Pentasaccharides, hexasaccharides and higher oligosaccharides are also produced
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-
?
additional information
?
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alternansucrase enzyme from Leuconostoc citreum SK24.002 is used to produce di-glycosyl-stevioside through acceptor reaction. Identification of the di-glycosyl-stevioside structure as 13-([alpha-D-glucopyranosyl-(1->3)-alpha-D-glucopyranosyl-(1->6)-beta-D glucopyranosyl-(1->2)-beta-D-glucopyranosyl]oxy)kaur-16-en-19-oic acid beta-D glucopyranosyl ester, method optimization and evaluation, overview
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-
additional information
?
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for the docking calculations, a model of the ASRDELTA2 glucosyl-enzyme intermediate is constructed based on the high resolution structure of the GH13 covalent intermediate (PDB ID 1S46). Maltose is the best known acceptor for ASR
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-
additional information
?
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product analysis, determination of alternan nanoparticle size distribution by dynamic light scattering
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additional information
?
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product analysis, determination of alternan nanoparticle size distribution by dynamic light scattering
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additional information
?
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Leuconostoc citreum ABK-1
product analysis, determination of alternan nanoparticle size distribution by dynamic light scattering
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-
-
additional information
?
-
Leuconostoc citreum NRRL B-1355
for the docking calculations, a model of the ASRDELTA2 glucosyl-enzyme intermediate is constructed based on the high resolution structure of the GH13 covalent intermediate (PDB ID 1S46). Maltose is the best known acceptor for ASR
-
-
-
additional information
?
-
alternansucrase enzyme from Leuconostoc citreum SK24.002 is used to produce di-glycosyl-stevioside through acceptor reaction. Identification of the di-glycosyl-stevioside structure as 13-([alpha-D-glucopyranosyl-(1->3)-alpha-D-glucopyranosyl-(1->6)-beta-D glucopyranosyl-(1->2)-beta-D-glucopyranosyl]oxy)kaur-16-en-19-oic acid beta-D glucopyranosyl ester, method optimization and evaluation, overview
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-
additional information
?
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methyl D-allopyrano-sides are glucosylated primarily at position 6, yielding methyl alpha-D-glucopyranosyl-(1,6)-D-allopyranosides. The latter subsequently gave rise to methyl alpha-D-glucopyranosyl-(1,6)-alpha-D-glucopyranosyl-(1,6)-D-allopyranosides. The methyl alpha-D-hexopyranosides are better acceptors than the corresponding beta-glycosides
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?
